# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

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

data_xzp5_1
_audit_block_doi                 10.5517/ccdc.csd.cc23fzbw
_database_code_depnum_ccdc_archive 'CCDC 1949848'
loop_
_audit_author_name
_audit_author_address
'Xie Zeping'
;Binzhou Medical University
China
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;
_chemical_name_systematic        (+)-Actinoxocine
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         320.33
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.6575(2)
_cell_length_b                   12.4737(3)
_cell_length_c                   15.9440(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1522.93(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9344
_cell_measurement_theta_min      4.5006
_cell_measurement_theta_max      72.4389
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            25301
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_theta_min         4.50
_diffrn_reflns_theta_max         72.43
_diffrn_reflns_theta_full        72.43
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3025
_reflns_number_gt                2958
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0694
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         3025
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.2582P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1238 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.40458(15) 0.40778(10) 0.41540(7) 0.0210(3) Uani d . . . 1 . .
O O2 0.81473(15) 0.45987(9) 0.44722(7) 0.0196(2) Uani d . . . 1 . .
O O3 0.86544(14) 0.34682(9) 0.56105(7) 0.0192(2) Uani d . . . 1 . .
O O4 0.87852(18) 0.48199(10) 0.78716(8) 0.0259(3) Uani d . . . 1 . .
H H4A 0.895(3) 0.5168(11) 0.8352(15) 0.039 Uiso calc U . R 1 . .
C C1 0.9226(2) 0.77271(13) 0.52229(11) 0.0202(3) Uani d . . . 1 . .
H H1 0.948466 0.845057 0.536136 0.024 Uiso calc U . R 1 . .
C C2 0.9040(2) 0.69635(13) 0.58719(10) 0.0185(3) Uani d . . . 1 . .
C C3 0.8652(2) 0.58537(13) 0.57092(10) 0.0166(3) Uani d . . . 1 . .
C C4 0.85538(19) 0.51387(13) 0.64209(10) 0.0166(3) Uani d . . . 1 . .
C C5 0.7981(2) 0.39763(13) 0.63558(10) 0.0178(3) Uani d . . . 1 . .
H H11 0.831578 0.356572 0.687003 0.021 Uiso calc U . R 1 . .
C C6 0.6020(2) 0.39449(12) 0.62177(10) 0.0172(3) Uani d . . . 1 . .
C C7 0.5777(2) 0.39051(12) 0.53623(10) 0.0166(3) Uani d . . . 1 . .
C C8 0.4128(2) 0.40285(13) 0.50119(10) 0.0180(3) Uani d . . . 1 . .
C C9 0.2341(2) 0.41659(16) 0.37854(11) 0.0281(4) Uani d . . . 1 . .
H H2 0.162875 0.355025 0.395481 0.042 Uiso calc U . R 1 . .
H H4 0.244776 0.417831 0.317295 0.042 Uiso calc U . R 1 . .
H H5 0.17835 0.482939 0.397684 0.042 Uiso calc U . R 1 . .
C C10 0.9232(3) 0.82304(14) 0.36885(11) 0.0266(4) Uani d . . . 1 . .
H H15 0.808304 0.837422 0.344177 0.04 Uiso calc U . R 1 . .
H H14 1.000584 0.792853 0.325988 0.04 Uiso calc U . R 1 . .
H H3 0.973109 0.890057 0.390155 0.04 Uiso calc U . R 1 . .
C C11 0.9039(2) 0.74431(13) 0.43995(11) 0.0199(3) Uani d . . . 1 . .
C C12 0.8628(2) 0.63701(13) 0.42253(10) 0.0190(3) Uani d . . . 1 . .
H H13 0.847169 0.616457 0.365644 0.023 Uiso calc U . R 1 . .
C C13 0.84393(19) 0.55998(13) 0.48368(11) 0.0169(3) Uani d . . . 1 . .
C C14 0.7514(2) 0.37187(13) 0.49435(10) 0.0180(3) Uani d . . . 1 . .
H H12 0.741676 0.308097 0.456639 0.022 Uiso calc U . R 1 . .
C C15 0.4623(2) 0.40315(13) 0.67701(10) 0.0199(3) Uani d . . . 1 . .
H H8 0.47925 0.405521 0.736008 0.024 Uiso calc U . R 1 . .
C C16 0.2963(2) 0.40817(14) 0.64167(11) 0.0211(3) Uani d . . . 1 . .
H H7 0.197611 0.410152 0.677721 0.025 Uiso calc U . R 1 . .
C C17 0.2699(2) 0.41041(13) 0.55493(11) 0.0204(3) Uani d . . . 1 . .
H H6 0.155276 0.417049 0.53278 0.025 Uiso calc U . R 1 . .
C C18 0.8854(2) 0.55335(13) 0.72168(10) 0.0190(3) Uani d . . . 1 . .
C C19 0.9200(2) 0.66274(14) 0.73723(11) 0.0219(3) Uani d . . . 1 . .
H H9 0.937053 0.68776 0.7929 0.026 Uiso calc U . R 1 . .
C C20 0.9284(2) 0.73167(13) 0.67141(11) 0.0213(3) Uani d . . . 1 . .
H H10 0.951181 0.80536 0.681774 0.026 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.3707(19) ?
O1 C9 . 1.436(2) ?
O2 C13 . 1.3955(19) ?
O2 C14 . 1.4158(19) ?
O3 C14 . 1.411(2) ?
O3 C5 . 1.4420(19) ?
O4 C18 . 1.373(2) ?
O4 H4A . 0.89(3) ?
C1 C11 . 1.367(2) ?
C1 C2 . 1.413(2) ?
C1 H1 . 0.95 ?
C2 C20 . 1.426(2) ?
C2 C3 . 1.440(2) ?
C3 C13 . 1.436(2) ?
C3 C4 . 1.445(2) ?
C4 C18 . 1.380(2) ?
C4 C5 . 1.518(2) ?
C5 C6 . 1.518(2) ?
C5 H11 . 1.0 ?
C6 C7 . 1.377(2) ?
C6 C15 . 1.390(2) ?
C7 C8 . 1.389(2) ?
C7 C14 . 1.507(2) ?
C8 C17 . 1.393(2) ?
C9 H2 . 0.98 ?
C9 H4 . 0.98 ?
C9 H5 . 0.98 ?
C10 C11 . 1.507(2) ?
C10 H15 . 0.98 ?
C10 H14 . 0.98 ?
C10 H3 . 0.98 ?
C11 C12 . 1.403(2) ?
C12 C13 . 1.376(2) ?
C12 H13 . 0.95 ?
C14 H12 . 1.0 ?
C15 C16 . 1.391(2) ?
C15 H8 . 0.95 ?
C16 C17 . 1.398(2) ?
C16 H7 . 0.95 ?
C17 H6 . 0.95 ?
C18 C19 . 1.412(2) ?
C19 C20 . 1.358(2) ?
C19 H9 . 0.95 ?
C20 H10 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C9 . . 116.99(13) ?
C13 O2 C14 . . 121.84(12) ?
C14 O3 C5 . . 107.62(11) ?
C18 O4 H4A . . 109.5 ?
C11 C1 C2 . . 121.19(15) ?
C11 C1 H1 . . 119.4 ?
C2 C1 H1 . . 119.4 ?
C1 C2 C20 . . 117.92(15) ?
C1 C2 C3 . . 122.47(15) ?
C20 C2 C3 . . 119.60(14) ?
C13 C3 C2 . . 114.21(14) ?
C13 C3 C4 . . 128.22(14) ?
C2 C3 C4 . . 117.56(14) ?
C18 C4 C3 . . 119.53(14) ?
C18 C4 C5 . . 116.85(14) ?
C3 C4 C5 . . 123.41(14) ?
O3 C5 C4 . . 111.89(13) ?
O3 C5 C6 . . 102.87(12) ?
C4 C5 C6 . . 108.67(13) ?
O3 C5 H11 . . 111.0 ?
C4 C5 H11 . . 111.0 ?
C6 C5 H11 . . 111.0 ?
C7 C6 C15 . . 121.74(15) ?
C7 C6 C5 . . 106.16(13) ?
C15 C6 C5 . . 131.87(15) ?
C6 C7 C8 . . 121.15(14) ?
C6 C7 C14 . . 108.96(13) ?
C8 C7 C14 . . 129.90(14) ?
O1 C8 C7 . . 116.64(14) ?
O1 C8 C17 . . 125.07(15) ?
C7 C8 C17 . . 118.29(14) ?
O1 C9 H2 . . 109.5 ?
O1 C9 H4 . . 109.5 ?
H2 C9 H4 . . 109.5 ?
O1 C9 H5 . . 109.5 ?
H2 C9 H5 . . 109.5 ?
H4 C9 H5 . . 109.5 ?
C11 C10 H15 . . 109.5 ?
C11 C10 H14 . . 109.5 ?
H15 C10 H14 . . 109.5 ?
C11 C10 H3 . . 109.5 ?
H15 C10 H3 . . 109.5 ?
H14 C10 H3 . . 109.5 ?
C1 C11 C12 . . 117.44(15) ?
C1 C11 C10 . . 122.90(15) ?
C12 C11 C10 . . 119.66(15) ?
C13 C12 C11 . . 123.32(15) ?
C13 C12 H13 . . 118.3 ?
C11 C12 H13 . . 118.3 ?
C12 C13 O2 . . 110.26(14) ?
C12 C13 C3 . . 121.36(14) ?
O2 C13 C3 . . 128.25(14) ?
O3 C14 O2 . . 111.10(12) ?
O3 C14 C7 . . 104.28(12) ?
O2 C14 C7 . . 114.70(13) ?
O3 C14 H12 . . 108.9 ?
O2 C14 H12 . . 108.9 ?
C7 C14 H12 . . 108.9 ?
C6 C15 C16 . . 116.73(15) ?
C6 C15 H8 . . 121.6 ?
C16 C15 H8 . . 121.6 ?
C15 C16 C17 . . 122.25(15) ?
C15 C16 H7 . . 118.9 ?
C17 C16 H7 . . 118.9 ?
C8 C17 C16 . . 119.58(15) ?
C8 C17 H6 . . 120.2 ?
C16 C17 H6 . . 120.2 ?
O4 C18 C4 . . 117.47(14) ?
O4 C18 C19 . . 120.02(15) ?
C4 C18 C19 . . 122.51(15) ?
C20 C19 C18 . . 119.02(15) ?
C20 C19 H9 . . 120.5 ?
C18 C19 H9 . . 120.5 ?
C19 C20 C2 . . 121.73(15) ?
C19 C20 H10 . . 119.1 ?
C2 C20 H10 . . 119.1 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 C1 C2 C20 . . . . 178.93(15) ?
C11 C1 C2 C3 . . . . 0.1(3) ?
C1 C2 C3 C13 . . . . -1.1(2) ?
C20 C2 C3 C13 . . . . -179.90(15) ?
C1 C2 C3 C4 . . . . 177.85(14) ?
C20 C2 C3 C4 . . . . -0.9(2) ?
C13 C3 C4 C18 . . . . 177.92(15) ?
C2 C3 C4 C18 . . . . -0.9(2) ?
C13 C3 C4 C5 . . . . -7.5(2) ?
C2 C3 C4 C5 . . . . 173.72(13) ?
C14 O3 C5 C4 . . . . -83.89(15) ?
C14 O3 C5 C6 . . . . 32.58(15) ?
C18 C4 C5 O3 . . . . -146.01(14) ?
C3 C4 C5 O3 . . . . 39.26(19) ?
C18 C4 C5 C6 . . . . 101.09(16) ?
C3 C4 C5 C6 . . . . -73.64(18) ?
O3 C5 C6 C7 . . . . -25.46(16) ?
C4 C5 C6 C7 . . . . 93.28(15) ?
O3 C5 C6 C15 . . . . 160.14(16) ?
C4 C5 C6 C15 . . . . -81.1(2) ?
C15 C6 C7 C8 . . . . 4.7(2) ?
C5 C6 C7 C8 . . . . -170.35(14) ?
C15 C6 C7 C14 . . . . -175.29(14) ?
C5 C6 C7 C14 . . . . 9.62(17) ?
C9 O1 C8 C7 . . . . 177.79(14) ?
C9 O1 C8 C17 . . . . -2.9(2) ?
C6 C7 C8 O1 . . . . 174.01(13) ?
C14 C7 C8 O1 . . . . -6.0(2) ?
C6 C7 C8 C17 . . . . -5.3(2) ?
C14 C7 C8 C17 . . . . 174.73(15) ?
C2 C1 C11 C12 . . . . 1.0(2) ?
C2 C1 C11 C10 . . . . -179.79(16) ?
C1 C11 C12 C13 . . . . -1.2(2) ?
C10 C11 C12 C13 . . . . 179.60(15) ?
C11 C12 C13 O2 . . . . -176.06(14) ?
C11 C12 C13 C3 . . . . 0.2(2) ?
C14 O2 C13 C12 . . . . -165.15(13) ?
C14 O2 C13 C3 . . . . 19.0(2) ?
C2 C3 C13 C12 . . . . 1.0(2) ?
C4 C3 C13 C12 . . . . -177.86(15) ?
C2 C3 C13 O2 . . . . 176.45(14) ?
C4 C3 C13 O2 . . . . -2.4(3) ?
C5 O3 C14 O2 . . . . 97.11(14) ?
C5 O3 C14 C7 . . . . -26.97(15) ?
C13 O2 C14 O3 . . . . -59.29(17) ?
C13 O2 C14 C7 . . . . 58.64(19) ?
C6 C7 C14 O3 . . . . 10.18(16) ?
C8 C7 C14 O3 . . . . -169.85(15) ?
C6 C7 C14 O2 . . . . -111.55(15) ?
C8 C7 C14 O2 . . . . 68.4(2) ?
C7 C6 C15 C16 . . . . -0.3(2) ?
C5 C6 C15 C16 . . . . 173.35(16) ?
C6 C15 C16 C17 . . . . -3.4(3) ?
O1 C8 C17 C16 . . . . -177.64(16) ?
C7 C8 C17 C16 . . . . 1.6(2) ?
C15 C16 C17 C8 . . . . 2.8(3) ?
C3 C4 C18 O4 . . . . -178.58(14) ?
C5 C4 C18 O4 . . . . 6.5(2) ?
C3 C4 C18 C19 . . . . 2.2(2) ?
C5 C4 C18 C19 . . . . -172.72(14) ?
O4 C18 C19 C20 . . . . 179.15(15) ?
C4 C18 C19 C20 . . . . -1.7(3) ?
C18 C19 C20 C2 . . . . -0.3(3) ?
C1 C2 C20 C19 . . . . -177.31(16) ?
C3 C2 C20 C19 . . . . 1.5(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4A O1 4_665 0.89 2.21 2.9714(18) 143.4 ?
O4 H4A O2 4_665 0.89 2.42 3.0378(17) 127.1 ?
C12 H13 O4 4_664 0.95 2.46 3.206(2) 135.1 ?
C17 H6 O3 1_455 0.95 2.43 3.1989(19) 138.1 ?
C19 H9 O1 4_665 0.95 2.59 3.263(2) 128.2 ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH and CH2Cl2'
_chemical_compound_source        Actinomyces
####################################################################### 
# 
# 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_xzp7
_database_code_depnum_ccdc_archive 'CCDC 1950507'
loop_
_audit_author_name
_audit_author_address
'Xie Zeping'
;Binzhou Medical University
China
;
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         322.34
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.9282(8)
_cell_length_b                   4.7315(3)
_cell_length_c                   27.471(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.048(5)
_cell_angle_gamma                90
_cell_volume                     1549.43(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1007
_cell_measurement_theta_min      3.2195
_cell_measurement_theta_max      67.2157
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680

_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            15513
_diffrn_reflns_av_R_equivalents  0.2082
_diffrn_reflns_av_unetI/netI     0.2261
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         72.54
_diffrn_reflns_theta_full        72.54
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33

_refine_special_details          
;
;

_reflns_number_total             5001
_reflns_number_gt                2651
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1809
_refine_ls_R_factor_gt           0.0904
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.2187
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_number_reflns         5001
_refine_ls_number_parameters     439
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.354
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.4(6)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2005(5) 0.5490(13) 0.1654(2) 0.0381(14) Uani d . . . 1 . .
O O2 0.6454(5) 0.4220(12) 0.0762(2) 0.0374(14) Uani d . . . 1 . .
O O3 0.3807(5) 0.6014(13) 0.0189(2) 0.0417(15) Uani d . . . 1 . .
H H33 0.374492 0.732056 -0.001761 0.063 Uiso calc U . R 1 . .
O O4 0.2375(5) 0.1754(13) 0.0117(2) 0.0402(15) Uani d . . . 1 . .
H H34 0.286068 0.295708 0.020215 0.06 Uiso calc U . R 1 . .
O O5 0.3253(5) 0.9064(14) 0.3101(2) 0.0420(15) Uani d . . . 1 . .
O O6 0.8143(5) 0.8885(11) 0.3600(2) 0.0346(13) Uani d . . . 1 . .
O O7 0.4670(5) 1.0232(12) 0.4262(2) 0.0349(13) Uani d . . . 1 . .
H H35 0.472761 1.158041 0.446058 0.052 Uiso calc U . R 1 . .
O O8 0.5511(5) 0.5665(12) 0.4663(2) 0.0354(13) Uani d . . . 1 . .
H H36 0.532052 0.719702 0.452959 0.053 Uiso calc U . R 1 . .
C C1 -0.1205(9) 0.092(2) 0.2470(4) 0.053(3) Uani d . . . 1 . .
H H3 -0.168634 0.258487 0.249831 0.08 Uiso calc U . R 1 . .
H H4 -0.074361 0.069317 0.276957 0.08 Uiso calc U . R 1 . .
H H1 -0.167333 -0.076497 0.24182 0.08 Uiso calc U . R 1 . .
C C2 -0.0455(8) 0.129(2) 0.2044(4) 0.045(2) Uani d . . . 1 . .
C C3 0.0422(8) 0.336(2) 0.2088(3) 0.039(2) Uani d . . . 1 . .
H H16 0.053171 0.446842 0.237441 0.047 Uiso calc U . R 1 . .
C C4 0.1094(7) 0.3662(18) 0.1695(3) 0.0355(19) Uani d . . . 1 . .
C C5 0.2494(7) 0.4950(17) 0.1171(3) 0.036(2) Uani d . . . 1 . .
H H5 0.25177 0.672943 0.097538 0.043 Uiso calc U . R 1 . .
C C6 0.3666(7) 0.3771(16) 0.1261(3) 0.0316(18) Uani d . . . 1 . .
C C7 0.4560(7) 0.4684(16) 0.0979(3) 0.0326(18) Uani d . . . 1 . .
C C8 0.5624(7) 0.3366(16) 0.1063(3) 0.0296(17) Uani d . . . 1 . .
C C9 0.7538(7) 0.300(2) 0.0857(4) 0.041(2) Uani d . . . 1 . .
H H10 0.77456 0.319975 0.120397 0.061 Uiso calc U . R 1 . .
H H11 0.809298 0.396343 0.066224 0.061 Uiso calc U . R 1 . .
H H2 0.751746 0.098552 0.077134 0.061 Uiso calc U . R 1 . .
C C10 0.3824(8) 0.1720(17) 0.1616(3) 0.0350(19) Uani d . . . 1 . .
H H6 0.32118 0.11307 0.180321 0.042 Uiso calc U . R 1 . .
C C11 0.4872(7) 0.0529(18) 0.1697(3) 0.0347(19) Uani d . . . 1 . .
H H12 0.4977 -0.084866 0.194643 0.042 Uiso calc U . R 1 . .
C C12 0.5775(7) 0.1314(16) 0.1421(3) 0.0332(18) Uani d . . . 1 . .
H H7 0.648774 0.045605 0.147661 0.04 Uiso calc U . R 1 . .
C C13 0.4442(7) 0.6998(17) 0.0607(3) 0.0322(18) Uani d . . . 1 . .
H H9 0.406017 0.864242 0.074987 0.039 Uiso calc U . R 1 . .
H H8 0.519474 0.761309 0.050889 0.039 Uiso calc U . R 1 . .
C C14 0.1719(7) 0.2830(17) 0.0930(3) 0.0327(18) Uani d . . . 1 . .
C C15 0.1640(7) 0.1378(17) 0.0485(3) 0.0337(18) Uani d . . . 1 . .
C C16 0.0781(7) -0.0621(19) 0.0411(4) 0.038(2) Uani d . . . 1 . .
H H15 0.072134 -0.157686 0.010701 0.046 Uiso calc U . R 1 . .
C C17 0.0014(7) -0.1261(19) 0.0763(4) 0.039(2) Uani d . . . 1 . .
H H14 -0.054843 -0.2641 0.069581 0.047 Uiso calc U . R 1 . .
C C18 0.0058(7) 0.0096(17) 0.1217(4) 0.039(2) Uani d . . . 1 . .
C C19 0.0914(8) 0.2099(18) 0.1275(3) 0.0353(19) Uani d . . . 1 . .
C C20 -0.0629(7) -0.0298(19) 0.1630(3) 0.039(2) Uani d . . . 1 . .
H H13 -0.120966 -0.16723 0.161636 0.046 Uiso calc U . R 1 . .
C C21 0.2413(8) 0.799(2) 0.2770(3) 0.043(2) Uani d . . . 1 . .
H H32 0.266145 0.820096 0.243527 0.065 Uiso calc U . R 1 . .
H H17 0.171391 0.904263 0.280694 0.065 Uiso calc U . R 1 . .
H H19 0.228547 0.598494 0.283817 0.065 Uiso calc U . R 1 . .
C C22 0.4304(7) 0.7872(18) 0.3085(3) 0.0354(19) Uani d . . . 1 . .
C C23 0.5085(7) 0.8938(17) 0.3433(3) 0.0288(17) Uani d . . . 1 . .
C C24 0.6178(7) 0.7755(16) 0.3445(3) 0.0314(18) Uani d . . . 1 . .
C C25 0.7047(7) 0.8620(18) 0.3833(3) 0.0330(18) Uani d . . . 1 . .
H H28 0.683315 1.046309 0.398213 0.04 Uiso calc U . R 1 . .
C C26 0.8870(7) 0.6957(17) 0.3821(3) 0.0352(19) Uani d . . . 1 . .
C C27 0.9972(7) 0.6418(18) 0.3712(3) 0.038(2) Uani d . . . 1 . .
H H25 1.033211 0.741459 0.346174 0.045 Uiso calc U . R 1 . .
C C28 1.0544(7) 0.4286(18) 0.3996(3) 0.036(2) Uani d . . . 1 . .
C C29 1.1762(7) 0.373(2) 0.3892(4) 0.046(2) Uani d . . . 1 . .
H H18 1.208278 0.243021 0.413766 0.069 Uiso calc U . R 1 . .
H H27 1.217916 0.551462 0.39038 0.069 Uiso calc U . R 1 . .
H H26 1.181413 0.288358 0.35681 0.069 Uiso calc U . R 1 . .
C C30 0.4777(7) 1.1290(16) 0.3771(3) 0.0293(17) Uani d . . . 1 . .
H H20 0.536107 1.27748 0.376963 0.035 Uiso calc U . R 1 . .
H H21 0.405747 1.214601 0.365618 0.035 Uiso calc U . R 1 . .
C C31 0.7239(7) 0.6402(17) 0.4227(3) 0.0312(18) Uani d . . . 1 . .
C C32 0.6619(7) 0.5144(17) 0.4583(3) 0.0333(18) Uani d . . . 1 . .
C C33 0.7144(7) 0.3041(18) 0.4883(3) 0.0357(19) Uani d . . . 1 . .
H H22 0.671713 0.217793 0.512734 0.043 Uiso calc U . R 1 . .
C C34 0.8229(7) 0.2199(17) 0.4837(3) 0.0354(19) Uani d . . . 1 . .
H H23 0.853997 0.078785 0.504761 0.042 Uiso calc U . R 1 . .
C C35 0.8893(7) 0.3430(17) 0.4476(3) 0.0353(19) Uani d . . . 1 . .
C C36 1.0034(8) 0.2832(18) 0.4367(3) 0.0362(19) Uani d . . . 1 . .
H H24 1.044212 0.144211 0.454905 0.043 Uiso calc U . R 1 . .
C C37 0.8351(7) 0.5508(16) 0.4191(3) 0.0326(18) Uani d . . . 1 . .
C C38 0.6461(8) 0.5699(17) 0.3111(3) 0.0368(19) Uani d . . . 1 . .
H H29 0.72004 0.495252 0.311651 0.044 Uiso calc U . R 1 . .
C C39 0.5667(8) 0.4726(18) 0.2768(3) 0.040(2) Uani d . . . 1 . .
H H30 0.586289 0.331036 0.254112 0.048 Uiso calc U . R 1 . .
C C40 0.4574(8) 0.5840(18) 0.2758(3) 0.037(2) Uani d . . . 1 . .
H H31 0.402789 0.518165 0.252472 0.044 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.396(10) ?
O1 C5 . 1.490(10) ?
O2 C8 . 1.375(9) ?
O2 C9 . 1.433(10) ?
O3 C13 . 1.432(10) ?
O3 H33 . 0.84 ?
O4 C15 . 1.374(9) ?
O4 H34 . 0.84 ?
O5 C22 . 1.377(11) ?
O5 C21 . 1.423(11) ?
O6 C26 . 1.385(11) ?
O6 C25 . 1.482(9) ?
O7 C30 . 1.449(9) ?
O7 H35 . 0.84 ?
O8 C32 . 1.369(10) ?
O8 H36 . 0.84 ?
C1 C2 . 1.509(12) ?
C1 H3 . 0.98 ?
C1 H4 . 0.98 ?
C1 H1 . 0.98 ?
C2 C20 . 1.373(14) ?
C2 C3 . 1.435(14) ?
C3 C4 . 1.376(11) ?
C3 H16 . 0.95 ?
C4 C19 . 1.380(13) ?
C5 C14 . 1.502(12) ?
C5 C6 . 1.517(12) ?
C5 H5 . 1.0 ?
C6 C10 . 1.384(13) ?
C6 C7 . 1.407(12) ?
C7 C8 . 1.426(11) ?
C7 C13 . 1.501(12) ?
C8 C12 . 1.389(12) ?
C9 H10 . 0.98 ?
C9 H11 . 0.98 ?
C9 H2 . 0.98 ?
C10 C11 . 1.382(12) ?
C10 H6 . 0.95 ?
C11 C12 . 1.390(11) ?
C11 H12 . 0.95 ?
C12 H7 . 0.95 ?
C13 H9 . 0.99 ?
C13 H8 . 0.99 ?
C14 C15 . 1.402(12) ?
C14 C19 . 1.418(11) ?
C15 C16 . 1.404(12) ?
C16 C17 . 1.388(13) ?
C16 H15 . 0.95 ?
C17 C18 . 1.402(13) ?
C17 H14 . 0.95 ?
C18 C19 . 1.398(12) ?
C18 C20 . 1.434(12) ?
C20 H13 . 0.95 ?
C21 H32 . 0.98 ?
C21 H17 . 0.98 ?
C21 H19 . 0.98 ?
C22 C40 . 1.363(12) ?
C22 C23 . 1.404(11) ?
C23 C24 . 1.418(12) ?
C23 C30 . 1.504(11) ?
C24 C38 . 1.387(11) ?
C24 C25 . 1.517(12) ?
C25 C31 . 1.519(12) ?
C25 H28 . 1.0 ?
C26 C27 . 1.381(11) ?
C26 C37 . 1.389(12) ?
C27 C28 . 1.432(13) ?
C27 H25 . 0.95 ?
C28 C36 . 1.389(12) ?
C28 C29 . 1.514(11) ?
C29 H18 . 0.98 ?
C29 H27 . 0.98 ?
C29 H26 . 0.98 ?
C30 H20 . 0.99 ?
C30 H21 . 0.99 ?
C31 C32 . 1.382(11) ?
C31 C37 . 1.400(11) ?
C32 C33 . 1.422(12) ?
C33 C34 . 1.364(12) ?
C33 H22 . 0.95 ?
C34 C35 . 1.417(12) ?
C34 H23 . 0.95 ?
C35 C37 . 1.400(12) ?
C35 C36 . 1.432(12) ?
C36 H24 . 0.95 ?
C38 C39 . 1.390(13) ?
C38 H29 . 0.95 ?
C39 C40 . 1.406(13) ?
C39 H30 . 0.95 ?
C40 H31 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C5 . . 107.3(6) ?
C8 O2 C9 . . 115.8(7) ?
C13 O3 H33 . . 109.5 ?
C15 O4 H34 . . 109.5 ?
C22 O5 C21 . . 117.0(7) ?
C26 O6 C25 . . 107.6(6) ?
C30 O7 H35 . . 109.5 ?
C32 O8 H36 . . 109.5 ?
C2 C1 H3 . . 109.5 ?
C2 C1 H4 . . 109.5 ?
H3 C1 H4 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H3 C1 H1 . . 109.5 ?
H4 C1 H1 . . 109.5 ?
C20 C2 C3 . . 122.2(8) ?
C20 C2 C1 . . 120.2(9) ?
C3 C2 C1 . . 117.7(9) ?
C4 C3 C2 . . 116.6(9) ?
C4 C3 H16 . . 121.7 ?
C2 C3 H16 . . 121.7 ?
C3 C4 C19 . . 121.5(9) ?
C3 C4 O1 . . 127.2(8) ?
C19 C4 O1 . . 111.3(7) ?
O1 C5 C14 . . 104.6(7) ?
O1 C5 C6 . . 107.9(7) ?
C14 C5 C6 . . 112.0(7) ?
O1 C5 H5 . . 110.7 ?
C14 C5 H5 . . 110.7 ?
C6 C5 H5 . . 110.7 ?
C10 C6 C7 . . 121.1(8) ?
C10 C6 C5 . . 118.2(7) ?
C7 C6 C5 . . 120.6(8) ?
C6 C7 C8 . . 117.6(8) ?
C6 C7 C13 . . 123.0(8) ?
C8 C7 C13 . . 119.4(8) ?
O2 C8 C12 . . 123.7(8) ?
O2 C8 C7 . . 115.4(7) ?
C12 C8 C7 . . 120.9(7) ?
O2 C9 H10 . . 109.5 ?
O2 C9 H11 . . 109.5 ?
H10 C9 H11 . . 109.5 ?
O2 C9 H2 . . 109.5 ?
H10 C9 H2 . . 109.5 ?
H11 C9 H2 . . 109.5 ?
C11 C10 C6 . . 120.0(8) ?
C11 C10 H6 . . 120.0 ?
C6 C10 H6 . . 120.0 ?
C10 C11 C12 . . 121.1(8) ?
C10 C11 H12 . . 119.5 ?
C12 C11 H12 . . 119.5 ?
C8 C12 C11 . . 119.3(8) ?
C8 C12 H7 . . 120.3 ?
C11 C12 H7 . . 120.3 ?
O3 C13 C7 . . 110.1(6) ?
O3 C13 H9 . . 109.6 ?
C7 C13 H9 . . 109.6 ?
O3 C13 H8 . . 109.6 ?
C7 C13 H8 . . 109.6 ?
H9 C13 H8 . . 108.2 ?
C15 C14 C19 . . 116.0(8) ?
C15 C14 C5 . . 137.2(8) ?
C19 C14 C5 . . 106.8(7) ?
O4 C15 C14 . . 123.6(8) ?
O4 C15 C16 . . 117.5(8) ?
C14 C15 C16 . . 118.8(8) ?
C17 C16 C15 . . 122.8(9) ?
C17 C16 H15 . . 118.6 ?
C15 C16 H15 . . 118.6 ?
C16 C17 C18 . . 121.1(8) ?
C16 C17 H14 . . 119.5 ?
C18 C17 H14 . . 119.5 ?
C19 C18 C17 . . 114.6(8) ?
C19 C18 C20 . . 115.7(9) ?
C17 C18 C20 . . 129.7(8) ?
C4 C19 C18 . . 123.4(8) ?
C4 C19 C14 . . 109.8(8) ?
C18 C19 C14 . . 126.8(8) ?
C2 C20 C18 . . 120.7(8) ?
C2 C20 H13 . . 119.7 ?
C18 C20 H13 . . 119.7 ?
O5 C21 H32 . . 109.5 ?
O5 C21 H17 . . 109.5 ?
H32 C21 H17 . . 109.5 ?
O5 C21 H19 . . 109.5 ?
H32 C21 H19 . . 109.5 ?
H17 C21 H19 . . 109.5 ?
C40 C22 O5 . . 123.1(8) ?
C40 C22 C23 . . 122.3(8) ?
O5 C22 C23 . . 114.5(7) ?
C22 C23 C24 . . 117.5(7) ?
C22 C23 C30 . . 121.0(7) ?
C24 C23 C30 . . 121.5(7) ?
C38 C24 C23 . . 120.4(8) ?
C38 C24 C25 . . 118.6(8) ?
C23 C24 C25 . . 120.9(7) ?
O6 C25 C24 . . 108.0(7) ?
O6 C25 C31 . . 104.7(6) ?
C24 C25 C31 . . 113.3(7) ?
O6 C25 H28 . . 110.2 ?
C24 C25 H28 . . 110.2 ?
C31 C25 H28 . . 110.2 ?
C27 C26 O6 . . 127.7(8) ?
C27 C26 C37 . . 121.3(8) ?
O6 C26 C37 . . 111.0(7) ?
C26 C27 C28 . . 116.8(8) ?
C26 C27 H25 . . 121.6 ?
C28 C27 H25 . . 121.6 ?
C36 C28 C27 . . 122.4(8) ?
C36 C28 C29 . . 120.0(9) ?
C27 C28 C29 . . 117.6(8) ?
C28 C29 H18 . . 109.5 ?
C28 C29 H27 . . 109.5 ?
H18 C29 H27 . . 109.5 ?
C28 C29 H26 . . 109.5 ?
H18 C29 H26 . . 109.5 ?
H27 C29 H26 . . 109.5 ?
O7 C30 C23 . . 110.6(6) ?
O7 C30 H20 . . 109.5 ?
C23 C30 H20 . . 109.5 ?
O7 C30 H21 . . 109.5 ?
C23 C30 H21 . . 109.5 ?
H20 C30 H21 . . 108.1 ?
C32 C31 C37 . . 116.9(8) ?
C32 C31 C25 . . 137.0(8) ?
C37 C31 C25 . . 106.1(7) ?
O8 C32 C31 . . 125.4(8) ?
O8 C32 C33 . . 116.2(8) ?
C31 C32 C33 . . 118.4(8) ?
C34 C33 C32 . . 123.4(8) ?
C34 C33 H22 . . 118.3 ?
C32 C33 H22 . . 118.3 ?
C33 C34 C35 . . 120.0(8) ?
C33 C34 H23 . . 120.0 ?
C35 C34 H23 . . 120.0 ?
C37 C35 C34 . . 114.9(8) ?
C37 C35 C36 . . 116.5(8) ?
C34 C35 C36 . . 128.6(9) ?
C28 C36 C35 . . 120.0(8) ?
C28 C36 H24 . . 120.0 ?
C35 C36 H24 . . 120.0 ?
C26 C37 C31 . . 110.6(8) ?
C26 C37 C35 . . 123.1(8) ?
C31 C37 C35 . . 126.3(8) ?
C24 C38 C39 . . 120.3(9) ?
C24 C38 H29 . . 119.8 ?
C39 C38 H29 . . 119.8 ?
C38 C39 C40 . . 119.9(8) ?
C38 C39 H30 . . 120.1 ?
C40 C39 H30 . . 120.1 ?
C22 C40 C39 . . 119.5(9) ?
C22 C40 H31 . . 120.2 ?
C39 C40 H31 . . 120.2 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C20 C2 C3 C4 . . . . -0.7(14) ?
C1 C2 C3 C4 . . . . -180.0(9) ?
C2 C3 C4 C19 . . . . 1.6(13) ?
C2 C3 C4 O1 . . . . -179.0(8) ?
C5 O1 C4 C3 . . . . 177.4(9) ?
C5 O1 C4 C19 . . . . -3.1(9) ?
C4 O1 C5 C14 . . . . 4.5(9) ?
C4 O1 C5 C6 . . . . -114.9(7) ?
O1 C5 C6 C10 . . . . 43.8(10) ?
C14 C5 C6 C10 . . . . -70.8(10) ?
O1 C5 C6 C7 . . . . -138.0(8) ?
C14 C5 C6 C7 . . . . 107.3(9) ?
C10 C6 C7 C8 . . . . 1.7(12) ?
C5 C6 C7 C8 . . . . -176.4(7) ?
C10 C6 C7 C13 . . . . -177.0(8) ?
C5 C6 C7 C13 . . . . 4.9(12) ?
C9 O2 C8 C12 . . . . -4.2(11) ?
C9 O2 C8 C7 . . . . 177.4(7) ?
C6 C7 C8 O2 . . . . 176.6(7) ?
C13 C7 C8 O2 . . . . -4.7(11) ?
C6 C7 C8 C12 . . . . -1.8(12) ?
C13 C7 C8 C12 . . . . 176.9(8) ?
C7 C6 C10 C11 . . . . -0.2(13) ?
C5 C6 C10 C11 . . . . 178.0(8) ?
C6 C10 C11 C12 . . . . -1.3(13) ?
O2 C8 C12 C11 . . . . -177.9(8) ?
C7 C8 C12 C11 . . . . 0.4(12) ?
C10 C11 C12 C8 . . . . 1.2(13) ?
C6 C7 C13 O3 . . . . -72.7(10) ?
C8 C7 C13 O3 . . . . 108.7(8) ?
O1 C5 C14 C15 . . . . 179.8(10) ?
C6 C5 C14 C15 . . . . -63.6(14) ?
O1 C5 C14 C19 . . . . -4.3(9) ?
C6 C5 C14 C19 . . . . 112.3(8) ?
C19 C14 C15 O4 . . . . -177.7(8) ?
C5 C14 C15 O4 . . . . -2.1(16) ?
C19 C14 C15 C16 . . . . 0.9(12) ?
C5 C14 C15 C16 . . . . 176.4(10) ?
O4 C15 C16 C17 . . . . 177.5(8) ?
C14 C15 C16 C17 . . . . -1.1(13) ?
C15 C16 C17 C18 . . . . 0.4(14) ?
C16 C17 C18 C19 . . . . 0.4(12) ?
C16 C17 C18 C20 . . . . -178.4(9) ?
C3 C4 C19 C18 . . . . -0.7(14) ?
O1 C4 C19 C18 . . . . 179.8(8) ?
C3 C4 C19 C14 . . . . 179.7(8) ?
O1 C4 C19 C14 . . . . 0.3(10) ?
C17 C18 C19 C4 . . . . 179.9(8) ?
C20 C18 C19 C4 . . . . -1.1(12) ?
C17 C18 C19 C14 . . . . -0.7(13) ?
C20 C18 C19 C14 . . . . 178.3(8) ?
C15 C14 C19 C4 . . . . 179.5(8) ?
C5 C14 C19 C4 . . . . 2.7(10) ?
C15 C14 C19 C18 . . . . 0.0(13) ?
C5 C14 C19 C18 . . . . -176.8(8) ?
C3 C2 C20 C18 . . . . -1.1(14) ?
C1 C2 C20 C18 . . . . 178.1(9) ?
C19 C18 C20 C2 . . . . 2.0(12) ?
C17 C18 C20 C2 . . . . -179.2(9) ?
C21 O5 C22 C40 . . . . 2.9(12) ?
C21 O5 C22 C23 . . . . -177.6(7) ?
C40 C22 C23 C24 . . . . -2.0(12) ?
O5 C22 C23 C24 . . . . 178.5(7) ?
C40 C22 C23 C30 . . . . 176.7(8) ?
O5 C22 C23 C30 . . . . -2.8(11) ?
C22 C23 C24 C38 . . . . 2.3(11) ?
C30 C23 C24 C38 . . . . -176.3(7) ?
C22 C23 C24 C25 . . . . -175.3(7) ?
C30 C23 C24 C25 . . . . 6.1(11) ?
C26 O6 C25 C24 . . . . -119.0(7) ?
C26 O6 C25 C31 . . . . 2.1(8) ?
C38 C24 C25 O6 . . . . 42.6(9) ?
C23 C24 C25 O6 . . . . -139.7(7) ?
C38 C24 C25 C31 . . . . -72.9(9) ?
C23 C24 C25 C31 . . . . 104.7(8) ?
C25 O6 C26 C27 . . . . 178.3(9) ?
C25 O6 C26 C37 . . . . -1.8(9) ?
O6 C26 C27 C28 . . . . -179.5(8) ?
C37 C26 C27 C28 . . . . 0.5(13) ?
C26 C27 C28 C36 . . . . -0.8(13) ?
C26 C27 C28 C29 . . . . -178.1(8) ?
C22 C23 C30 O7 . . . . 108.2(8) ?
C24 C23 C30 O7 . . . . -73.2(9) ?
O6 C25 C31 C32 . . . . 178.8(10) ?
C24 C25 C31 C32 . . . . -63.7(13) ?
O6 C25 C31 C37 . . . . -1.7(8) ?
C24 C25 C31 C37 . . . . 115.8(8) ?
C37 C31 C32 O8 . . . . -177.5(8) ?
C25 C31 C32 O8 . . . . 1.9(16) ?
C37 C31 C32 C33 . . . . -0.4(12) ?
C25 C31 C32 C33 . . . . 179.1(9) ?
O8 C32 C33 C34 . . . . 177.4(8) ?
C31 C32 C33 C34 . . . . 0.0(13) ?
C32 C33 C34 C35 . . . . -0.2(14) ?
C33 C34 C35 C37 . . . . 0.7(12) ?
C33 C34 C35 C36 . . . . -179.5(9) ?
C27 C28 C36 C35 . . . . 0.5(13) ?
C29 C28 C36 C35 . . . . 177.8(8) ?
C37 C35 C36 C28 . . . . 0.0(12) ?
C34 C35 C36 C28 . . . . -179.8(8) ?
C27 C26 C37 C31 . . . . -179.4(8) ?
O6 C26 C37 C31 . . . . 0.7(10) ?
C27 C26 C37 C35 . . . . 0.0(13) ?
O6 C26 C37 C35 . . . . 180.0(7) ?
C32 C31 C37 C26 . . . . -179.7(8) ?
C25 C31 C37 C26 . . . . 0.7(10) ?
C32 C31 C37 C35 . . . . 1.0(13) ?
C25 C31 C37 C35 . . . . -178.6(8) ?
C34 C35 C37 C26 . . . . 179.6(8) ?
C36 C35 C37 C26 . . . . -0.2(12) ?
C34 C35 C37 C31 . . . . -1.2(13) ?
C36 C35 C37 C31 . . . . 179.0(8) ?
C23 C24 C38 C39 . . . . -1.6(12) ?
C25 C24 C38 C39 . . . . 176.1(7) ?
C24 C38 C39 C40 . . . . 0.3(13) ?
O5 C22 C40 C39 . . . . -179.8(8) ?
C23 C22 C40 C39 . . . . 0.8(13) ?
C38 C39 C40 C22 . . . . 0.1(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H33 O2 2_655 0.84 2.24 3.026(9) 156.3 ?
O4 H34 O3 . 0.84 1.84 2.645(8) 161.2 ?
O7 H35 O8 1_565 0.84 2.21 2.958(8) 148.4 ?
O7 H35 O8 2_656 0.84 2.47 2.975(8) 119.2 ?
O8 H36 O7 . 0.84 1.78 2.609(8) 169.8 ?
C9 H11 O4 2_655 0.98 2.56 3.217(11) 124.6 ?
C21 H32 O1 . 0.98 2.60 3.305(11) 129.2 ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH and CH2Cl2'
####################################################################### 
# 
# 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_xzp5
_database_code_depnum_ccdc_archive 'CCDC 1950508'
loop_
_audit_author_name
_audit_author_address
'Xie Zeping'
;Binzhou Medical University
China
;
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         320.33

_chemical_melting_point          ?

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

_cell_length_a                   7.8685(2)
_cell_length_b                   11.5144(2)
_cell_length_c                   16.5769(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.3720(10)
_cell_angle_gamma                90
_cell_volume                     1461.17(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      2.7399
_cell_measurement_theta_max      72.3694
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            25663
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         72.36
_diffrn_reflns_theta_full        72.36
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             2876
_reflns_number_gt                2858
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.1837
_refine_ls_goodness_of_fit_ref   1.810
_refine_ls_restrained_S_all      1.810
_refine_ls_number_reflns         2876
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.23526(9) 0.20318(7) 0.43851(4) 0.0129(3) Uani d . . . 1 . .
O O2 0.14693(9) 0.48745(6) 0.39889(4) 0.0146(3) Uani d . . . 1 . .
O O3 0.13194(9) 0.19512(6) 0.55929(5) 0.0133(3) Uani d . . . 1 . .
O O4 0.48116(11) 0.17075(8) 0.77236(5) 0.0189(3) Uani d . . . 1 . .
H H4A 0.5475(19) 0.1381(15) 0.8147(10) 0.028 Uiso calc U . R 1 . .
C C1 0.74482(14) 0.09960(10) 0.34219(7) 0.0171(3) Uani d . . . 1 . .
H H1 0.868528 0.079736 0.362178 0.026 Uiso calc U . R 1 . .
H H15 0.73434 0.171205 0.309456 0.026 Uiso calc U . R 1 . .
H H14 0.684497 0.036323 0.307506 0.026 Uiso calc U . R 1 . .
C C2 0.66335(14) 0.11734(9) 0.41523(7) 0.0134(3) Uani d . . . 1 . .
C C3 0.49005(13) 0.15662(9) 0.40327(7) 0.0127(3) Uani d . . . 1 . .
H H13 0.424956 0.170408 0.348279 0.015 Uiso calc U . R 1 . .
C C4 0.41034(13) 0.17605(9) 0.46826(7) 0.0112(3) Uani d . . . 1 . .
C C5 0.13682(13) 0.26106(9) 0.48799(6) 0.0115(3) Uani d . . . 1 . .
H H12 0.014871 0.273114 0.454668 0.014 Uiso calc U . R 1 . .
C C6 0.21241(12) 0.37615(9) 0.52150(6) 0.0114(3) Uani d . . . 1 . .
C C7 0.21871(12) 0.48259(9) 0.48234(6) 0.0116(3) Uani d . . . 1 . .
C C8 0.15087(14) 0.59850(9) 0.35964(7) 0.0164(3) Uani d . . . 1 . .
H H4 0.084246 0.654981 0.384085 0.025 Uiso calc U . R 1 . .
H H5 0.098921 0.591371 0.300128 0.025 Uiso calc U . R 1 . .
H H2 0.272142 0.6248 0.367949 0.025 Uiso calc U . R 1 . .
C C9 0.75419(14) 0.09502(9) 0.49445(7) 0.0134(3) Uani d . . . 1 . .
H H3 0.869786 0.065417 0.503719 0.016 Uiso calc U . R 1 . .
C C10 0.29639(13) 0.57634(9) 0.53001(7) 0.0143(3) Uani d . . . 1 . .
H H6 0.30015 0.650216 0.504969 0.017 Uiso calc U . R 1 . .
C C11 0.36884(14) 0.56170(10) 0.61472(7) 0.0161(3) Uani d . . . 1 . .
H H7 0.419879 0.626695 0.646607 0.019 Uiso calc U . R 1 . .
C C12 0.36833(13) 0.45458(9) 0.65372(6) 0.0136(3) Uani d . . . 1 . .
H H11 0.421421 0.444426 0.710868 0.016 Uiso calc U . R 1 . .
C C13 0.28672(12) 0.36357(9) 0.60519(6) 0.0117(3) Uani d . . . 1 . .
C C14 0.27016(13) 0.23630(9) 0.62584(6) 0.0116(3) Uani d . . . 1 . .
H H8 0.237946 0.227452 0.68044 0.014 Uiso calc U . R 1 . .
C C15 0.44136(13) 0.17702(9) 0.62699(6) 0.0111(3) Uani d . . . 1 . .
C C16 0.54657(13) 0.15114(9) 0.70349(6) 0.0134(3) Uani d . . . 1 . .
C C17 0.71801(14) 0.10818(10) 0.71292(7) 0.0152(3) Uani d . . . 1 . .
H H9 0.787962 0.090979 0.766401 0.018 Uiso calc U . R 1 . .
C C18 0.78157(13) 0.09176(9) 0.64371(7) 0.0145(3) Uani d . . . 1 . .
H H10 0.897461 0.063881 0.649739 0.017 Uiso calc U . R 1 . .
C C19 0.67888(13) 0.11530(9) 0.56307(7) 0.0119(3) Uani d . . . 1 . .
C C20 0.50366(13) 0.15801(8) 0.55274(6) 0.0116(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.3872(12) ?
O1 C5 . 1.4180(12) ?
O2 C7 . 1.3691(12) ?
O2 C8 . 1.4383(12) ?
O3 C5 . 1.4127(12) ?
O3 C14 . 1.4387(12) ?
O4 C16 . 1.3752(13) ?
O4 H4A . 0.858(19) ?
C1 C2 . 1.5092(14) ?
C1 H1 . 0.98 ?
C1 H15 . 0.98 ?
C1 H14 . 0.98 ?
C2 C9 . 1.3665(15) ?
C2 C3 . 1.4065(15) ?
C3 C4 . 1.3844(15) ?
C3 H13 . 0.95 ?
C4 C20 . 1.4379(13) ?
C5 C6 . 1.5052(13) ?
C5 H12 . 1.0 ?
C6 C13 . 1.3828(14) ?
C6 C7 . 1.3933(14) ?
C7 C10 . 1.3927(15) ?
C8 H4 . 0.98 ?
C8 H5 . 0.98 ?
C8 H2 . 0.98 ?
C9 C19 . 1.4182(15) ?
C9 H3 . 0.95 ?
C10 C11 . 1.3983(14) ?
C10 H6 . 0.95 ?
C11 C12 . 1.3930(15) ?
C11 H7 . 0.95 ?
C12 C13 . 1.3852(14) ?
C12 H11 . 0.95 ?
C13 C14 . 1.5174(14) ?
C14 C15 . 1.5063(14) ?
C14 H8 . 1.0 ?
C15 C16 . 1.3772(14) ?
C15 C20 . 1.4430(14) ?
C16 C17 . 1.4112(15) ?
C17 C18 . 1.3665(15) ?
C17 H9 . 0.95 ?
C18 C19 . 1.4191(14) ?
C18 H10 . 0.95 ?
C19 C20 . 1.4363(14) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C5 . . 122.04(8) ?
C7 O2 C8 . . 116.51(8) ?
C5 O3 C14 . . 107.60(7) ?
C16 O4 H4A . . 109.5 ?
C2 C1 H1 . . 109.5 ?
C2 C1 H15 . . 109.5 ?
H1 C1 H15 . . 109.5 ?
C2 C1 H14 . . 109.5 ?
H1 C1 H14 . . 109.5 ?
H15 C1 H14 . . 109.5 ?
C9 C2 C3 . . 118.07(10) ?
C9 C2 C1 . . 121.38(9) ?
C3 C2 C1 . . 120.55(10) ?
C4 C3 C2 . . 122.76(10) ?
C4 C3 H13 . . 118.6 ?
C2 C3 H13 . . 118.6 ?
C3 C4 O1 . . 110.55(9) ?
C3 C4 C20 . . 120.88(9) ?
O1 C4 C20 . . 128.33(9) ?
O3 C5 O1 . . 110.83(8) ?
O3 C5 C6 . . 104.43(8) ?
O1 C5 C6 . . 113.90(8) ?
O3 C5 H12 . . 109.2 ?
O1 C5 H12 . . 109.2 ?
C6 C5 H12 . . 109.2 ?
C13 C6 C7 . . 120.48(9) ?
C13 C6 C5 . . 108.51(8) ?
C7 C6 C5 . . 131.01(9) ?
O2 C7 C10 . . 124.47(9) ?
O2 C7 C6 . . 117.12(9) ?
C10 C7 C6 . . 118.40(9) ?
O2 C8 H4 . . 109.5 ?
O2 C8 H5 . . 109.5 ?
H4 C8 H5 . . 109.5 ?
O2 C8 H2 . . 109.5 ?
H4 C8 H2 . . 109.5 ?
H5 C8 H2 . . 109.5 ?
C2 C9 C19 . . 121.14(10) ?
C2 C9 H3 . . 119.4 ?
C19 C9 H3 . . 119.4 ?
C7 C10 C11 . . 120.00(10) ?
C7 C10 H6 . . 120.0 ?
C11 C10 H6 . . 120.0 ?
C12 C11 C10 . . 121.91(10) ?
C12 C11 H7 . . 119.0 ?
C10 C11 H7 . . 119.0 ?
C13 C12 C11 . . 116.81(10) ?
C13 C12 H11 . . 121.6 ?
C11 C12 H11 . . 121.6 ?
C6 C13 C12 . . 122.35(9) ?
C6 C13 C14 . . 106.80(9) ?
C12 C13 C14 . . 130.70(10) ?
O3 C14 C15 . . 112.06(8) ?
O3 C14 C13 . . 103.56(8) ?
C15 C14 C13 . . 108.50(8) ?
O3 C14 H8 . . 110.8 ?
C15 C14 H8 . . 110.8 ?
C13 C14 H8 . . 110.8 ?
C16 C15 C20 . . 120.14(9) ?
C16 C15 C14 . . 117.07(9) ?
C20 C15 C14 . . 122.49(9) ?
O4 C16 C15 . . 117.92(9) ?
O4 C16 C17 . . 119.82(9) ?
C15 C16 C17 . . 122.24(10) ?
C18 C17 C16 . . 118.79(10) ?
C18 C17 H9 . . 120.6 ?
C16 C17 H9 . . 120.6 ?
C17 C18 C19 . . 121.69(9) ?
C17 C18 H10 . . 119.2 ?
C19 C18 H10 . . 119.2 ?
C9 C19 C18 . . 118.14(9) ?
C9 C19 C20 . . 121.90(10) ?
C18 C19 C20 . . 119.96(9) ?
C19 C20 C4 . . 115.18(9) ?
C19 C20 C15 . . 117.15(9) ?
C4 C20 C15 . . 127.67(9) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C2 C3 C4 . . . . 1.62(15) ?
C1 C2 C3 C4 . . . . -178.92(10) ?
C2 C3 C4 O1 . . . . -174.12(8) ?
C2 C3 C4 C20 . . . . 0.82(16) ?
C5 O1 C4 C3 . . . . -160.08(9) ?
C5 O1 C4 C20 . . . . 25.46(15) ?
C14 O3 C5 O1 . . . . 94.75(9) ?
C14 O3 C5 C6 . . . . -28.31(9) ?
C4 O1 C5 O3 . . . . -60.49(11) ?
C4 O1 C5 C6 . . . . 56.92(12) ?
O3 C5 C6 C13 . . . . 14.85(10) ?
O1 C5 C6 C13 . . . . -106.19(9) ?
O3 C5 C6 C7 . . . . -166.25(9) ?
O1 C5 C6 C7 . . . . 72.71(13) ?
C8 O2 C7 C10 . . . . -1.21(14) ?
C8 O2 C7 C6 . . . . 178.65(8) ?
C13 C6 C7 O2 . . . . 178.10(8) ?
C5 C6 C7 O2 . . . . -0.69(15) ?
C13 C6 C7 C10 . . . . -2.03(14) ?
C5 C6 C7 C10 . . . . 179.18(9) ?
C3 C2 C9 C19 . . . . -2.54(15) ?
C1 C2 C9 C19 . . . . 178.00(9) ?
O2 C7 C10 C11 . . . . -178.84(9) ?
C6 C7 C10 C11 . . . . 1.30(15) ?
C7 C10 C11 C12 . . . . 0.90(16) ?
C10 C11 C12 C13 . . . . -2.30(15) ?
C7 C6 C13 C12 . . . . 0.59(14) ?
C5 C6 C13 C12 . . . . 179.63(9) ?
C7 C6 C13 C14 . . . . -175.37(9) ?
C5 C6 C13 C14 . . . . 3.67(10) ?
C11 C12 C13 C6 . . . . 1.56(15) ?
C11 C12 C13 C14 . . . . 176.46(9) ?
C5 O3 C14 C15 . . . . -86.32(9) ?
C5 O3 C14 C13 . . . . 30.42(9) ?
C6 C13 C14 O3 . . . . -20.48(10) ?
C12 C13 C14 O3 . . . . 164.02(10) ?
C6 C13 C14 C15 . . . . 98.73(9) ?
C12 C13 C14 C15 . . . . -76.77(13) ?
O3 C14 C15 C16 . . . . -142.04(9) ?
C13 C14 C15 C16 . . . . 104.23(11) ?
O3 C14 C15 C20 . . . . 44.23(13) ?
C13 C14 C15 C20 . . . . -69.50(12) ?
C20 C15 C16 O4 . . . . -179.96(9) ?
C14 C15 C16 O4 . . . . 6.15(15) ?
C20 C15 C16 C17 . . . . 1.42(17) ?
C14 C15 C16 C17 . . . . -172.47(10) ?
O4 C16 C17 C18 . . . . -178.59(10) ?
C15 C16 C17 C18 . . . . 0.01(17) ?
C16 C17 C18 C19 . . . . -0.87(17) ?
C2 C9 C19 C18 . . . . -179.11(9) ?
C2 C9 C19 C20 . . . . 1.12(16) ?
C17 C18 C19 C9 . . . . -179.49(9) ?
C17 C18 C19 C20 . . . . 0.29(16) ?
C9 C19 C20 C4 . . . . 1.26(14) ?
C18 C19 C20 C4 . . . . -178.51(9) ?
C9 C19 C20 C15 . . . . -179.14(9) ?
C18 C19 C20 C15 . . . . 1.09(14) ?
C3 C4 C20 C19 . . . . -2.17(15) ?
O1 C4 C20 C19 . . . . 171.78(9) ?
C3 C4 C20 C15 . . . . 178.27(9) ?
O1 C4 C20 C15 . . . . -7.77(19) ?
C16 C15 C20 C19 . . . . -1.92(15) ?
C14 C15 C20 C19 . . . . 171.62(9) ?
C16 C15 C20 C4 . . . . 177.63(9) ?
C14 C15 C20 C4 . . . . -8.83(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4A O2 4_666 0.86 2.04 2.8554(11) 159.4 ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH and CH2Cl2'
_chemical_compound_source        Actinomyces
####################################################################### 
# 
# 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_xzp5_2
_database_code_depnum_ccdc_archive 'CCDC 1950506'
loop_
_audit_author_name
_audit_author_address
'Xie Zeping'
;Binzhou Medical University
China
;
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         320.33
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.6647(2)
_cell_length_b                   12.4751(4)
_cell_length_c                   15.9554(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1525.62(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9435
_cell_measurement_theta_min      4.4991
_cell_measurement_theta_max      72.3066
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       nedle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            29366
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_theta_min         4.50
_diffrn_reflns_theta_max         73.17
_diffrn_reflns_theta_full        73.17
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3048
_reflns_number_gt                2703
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1479
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         3048
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0867P)²+0.5671P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0019(7)
_refine_ls_abs_structure_details 
;

Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(14)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1851(3) 0.5403(2) 0.55274(16) 0.0337(6) Uani d . . . 1 . .
O O2 0.5954(3) 0.5925(2) 0.58458(16) 0.0352(6) Uani d . . . 1 . .
O O3 0.1217(4) 0.5183(2) 0.21274(17) 0.0394(6) Uani d . . . 1 . .
H H3A 0.113(7) 0.479(2) 0.160(3) 0.059 Uiso calc U . R 1 . .
O O4 0.1343(3) 0.6530(2) 0.43902(16) 0.0343(6) Uani d . . . 1 . .
C C1 0.0768(6) 0.1769(3) 0.6311(3) 0.0400(9) Uani d . . . 1 . .
H H9 0.020004 0.111568 0.610731 0.06 Uiso calc U . R 1 . .
H H1 0.005839 0.20891 0.675702 0.06 Uiso calc U . R 1 . .
H H10 0.19253 0.159181 0.653223 0.06 Uiso calc U . R 1 . .
C C2 0.0952(5) 0.2557(3) 0.5599(2) 0.0334(8) Uani d . . . 1 . .
C C3 0.1368(5) 0.3631(3) 0.5774(2) 0.0329(8) Uani d . . . 1 . .
H H12 0.152516 0.383628 0.634218 0.04 Uiso calc U . R 1 . .
C C4 0.1559(4) 0.4399(3) 0.5161(2) 0.0308(8) Uani d . . . 1 . .
C C5 0.2487(5) 0.6278(3) 0.5057(2) 0.0325(8) Uani d . . . 1 . .
H H11 0.258829 0.691624 0.543307 0.039 Uiso calc U . R 1 . .
C C6 0.4216(4) 0.6091(3) 0.4637(2) 0.0303(7) Uani d . . . 1 . .
C C7 0.5868(5) 0.5968(3) 0.4989(2) 0.0299(7) Uani d . . . 1 . .
C C8 0.7661(5) 0.5831(4) 0.6213(3) 0.0431(9) Uani d . . . 1 . .
H H4 0.819798 0.515563 0.603479 0.065 Uiso calc U . R 1 . .
H H2 0.755989 0.584051 0.682555 0.065 Uiso calc U . R 1 . .
H H3 0.838847 0.643309 0.602998 0.065 Uiso calc U . R 1 . .
C C9 0.7300(4) 0.5897(3) 0.4451(2) 0.0335(8) Uani d . . . 1 . .
H H15 0.84466 0.583504 0.467246 0.04 Uiso calc U . R 1 . .
C C10 0.7034(5) 0.5919(3) 0.3584(2) 0.0357(8) Uani d . . . 1 . .
H H5 0.80214 0.590139 0.322377 0.043 Uiso calc U . R 1 . .
C C11 0.5380(5) 0.5966(3) 0.3229(2) 0.0333(8) Uani d . . . 1 . .
H H14 0.521223 0.594081 0.26395 0.04 Uiso calc U . R 1 . .
C C12 0.3975(4) 0.6053(3) 0.3783(2) 0.0303(7) Uani d . . . 1 . .
C C13 0.2024(5) 0.6025(3) 0.3641(2) 0.0325(7) Uani d . . . 1 . .
H H13 0.169145 0.643528 0.312696 0.039 Uiso calc U . R 1 . .
C C14 0.1453(4) 0.4863(3) 0.3579(2) 0.0305(7) Uani d . . . 1 . .
C C15 0.1145(5) 0.4466(3) 0.2784(2) 0.0319(8) Uani d . . . 1 . .
C C16 0.0796(5) 0.3374(3) 0.2627(2) 0.0358(8) Uani d . . . 1 . .
H H6 0.061775 0.312487 0.207117 0.043 Uiso calc U . R 1 . .
C C17 0.0721(5) 0.2688(3) 0.3285(2) 0.0353(8) Uani d . . . 1 . .
H H7 0.050609 0.194993 0.317959 0.042 Uiso calc U . R 1 . .
C C18 0.0953(5) 0.3034(3) 0.4127(2) 0.0316(8) Uani d . . . 1 . .
C C19 0.0775(5) 0.2274(3) 0.4774(2) 0.0333(8) Uani d . . . 1 . .
H H8 0.052726 0.154936 0.463561 0.04 Uiso calc U . R 1 . .
C C20 0.1348(4) 0.4143(3) 0.4291(2) 0.0299(7) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.399(4) ?
O1 C5 . 1.412(4) ?
O2 C7 . 1.369(4) ?
O2 C8 . 1.438(5) ?
O3 C15 . 1.380(4) ?
O3 H3A . 0.98(6) ?
O4 C5 . 1.414(4) ?
O4 C13 . 1.448(4) ?
C1 C2 . 1.508(5) ?
C1 H9 . 0.98 ?
C1 H1 . 0.98 ?
C1 H10 . 0.98 ?
C2 C19 . 1.370(5) ?
C2 C3 . 1.405(5) ?
C3 C4 . 1.377(5) ?
C3 H12 . 0.95 ?
C4 C20 . 1.434(5) ?
C5 C6 . 1.503(5) ?
C5 H11 . 1.0 ?
C6 C12 . 1.376(5) ?
C6 C7 . 1.394(5) ?
C7 C9 . 1.397(5) ?
C8 H4 . 0.98 ?
C8 H2 . 0.98 ?
C8 H3 . 0.98 ?
C9 C10 . 1.399(5) ?
C9 H15 . 0.95 ?
C10 C11 . 1.390(5) ?
C10 H5 . 0.95 ?
C11 C12 . 1.397(5) ?
C11 H14 . 0.95 ?
C12 C13 . 1.513(5) ?
C13 C14 . 1.517(5) ?
C13 H13 . 1.0 ?
C14 C15 . 1.381(5) ?
C14 C20 . 1.451(5) ?
C15 C16 . 1.410(5) ?
C16 C17 . 1.356(5) ?
C16 H6 . 0.95 ?
C17 C18 . 1.423(5) ?
C17 H7 . 0.95 ?
C18 C19 . 1.408(5) ?
C18 C20 . 1.441(5) ?
C19 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C5 . . 121.7(3) ?
C7 O2 C8 . . 117.0(3) ?
C15 O3 H3A . . 109.5 ?
C5 O4 C13 . . 107.5(3) ?
C2 C1 H9 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H9 C1 H1 . . 109.5 ?
C2 C1 H10 . . 109.5 ?
H9 C1 H10 . . 109.5 ?
H1 C1 H10 . . 109.5 ?
C19 C2 C3 . . 117.3(3) ?
C19 C2 C1 . . 123.2(3) ?
C3 C2 C1 . . 119.5(3) ?
C4 C3 C2 . . 123.2(3) ?
C4 C3 H12 . . 118.4 ?
C2 C3 H12 . . 118.4 ?
C3 C4 O1 . . 110.1(3) ?
C3 C4 C20 . . 121.3(3) ?
O1 C4 C20 . . 128.4(3) ?
O1 C5 O4 . . 110.9(3) ?
O1 C5 C6 . . 114.9(3) ?
O4 C5 C6 . . 104.3(3) ?
O1 C5 H11 . . 108.8 ?
O4 C5 H11 . . 108.8 ?
C6 C5 H11 . . 108.8 ?
C12 C6 C7 . . 121.2(3) ?
C12 C6 C5 . . 109.2(3) ?
C7 C6 C5 . . 129.7(3) ?
O2 C7 C6 . . 116.8(3) ?
O2 C7 C9 . . 125.0(3) ?
C6 C7 C9 . . 118.3(3) ?
O2 C8 H4 . . 109.5 ?
O2 C8 H2 . . 109.5 ?
H4 C8 H2 . . 109.5 ?
O2 C8 H3 . . 109.5 ?
H4 C8 H3 . . 109.5 ?
H2 C8 H3 . . 109.5 ?
C7 C9 C10 . . 119.5(3) ?
C7 C9 H15 . . 120.3 ?
C10 C9 H15 . . 120.3 ?
C11 C10 C9 . . 122.4(3) ?
C11 C10 H5 . . 118.8 ?
C9 C10 H5 . . 118.8 ?
C10 C11 C12 . . 116.7(3) ?
C10 C11 H14 . . 121.7 ?
C12 C11 H14 . . 121.7 ?
C6 C12 C11 . . 121.7(3) ?
C6 C12 C13 . . 106.4(3) ?
C11 C12 C13 . . 131.7(3) ?
O4 C13 C12 . . 102.9(3) ?
O4 C13 C14 . . 111.5(3) ?
C12 C13 C14 . . 108.5(3) ?
O4 C13 H13 . . 111.2 ?
C12 C13 H13 . . 111.2 ?
C14 C13 H13 . . 111.2 ?
C15 C14 C20 . . 119.2(3) ?
C15 C14 C13 . . 116.9(3) ?
C20 C14 C13 . . 123.8(3) ?
O3 C15 C14 . . 117.2(3) ?
O3 C15 C16 . . 119.9(3) ?
C14 C15 C16 . . 122.8(3) ?
C17 C16 C15 . . 118.7(4) ?
C17 C16 H6 . . 120.6 ?
C15 C16 H6 . . 120.6 ?
C16 C17 C18 . . 122.3(4) ?
C16 C17 H7 . . 118.9 ?
C18 C17 H7 . . 118.9 ?
C19 C18 C17 . . 118.4(3) ?
C19 C18 C20 . . 122.2(3) ?
C17 C18 C20 . . 119.3(3) ?
C2 C19 C18 . . 121.5(3) ?
C2 C19 H8 . . 119.3 ?
C18 C19 H8 . . 119.3 ?
C4 C20 C18 . . 114.5(3) ?
C4 C20 C14 . . 127.9(3) ?
C18 C20 C14 . . 117.6(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C19 C2 C3 C4 . . . . 1.6(5) ?
C1 C2 C3 C4 . . . . -180.0(3) ?
C2 C3 C4 O1 . . . . 175.9(3) ?
C2 C3 C4 C20 . . . . -0.3(5) ?
C5 O1 C4 C3 . . . . 165.0(3) ?
C5 O1 C4 C20 . . . . -19.1(5) ?
C4 O1 C5 O4 . . . . 59.6(4) ?
C4 O1 C5 C6 . . . . -58.4(4) ?
C13 O4 C5 O1 . . . . -97.7(3) ?
C13 O4 C5 C6 . . . . 26.5(3) ?
O1 C5 C6 C12 . . . . 111.6(3) ?
O4 C5 C6 C12 . . . . -10.1(4) ?
O1 C5 C6 C7 . . . . -68.6(5) ?
O4 C5 C6 C7 . . . . 169.8(3) ?
C8 O2 C7 C6 . . . . -178.1(3) ?
C8 O2 C7 C9 . . . . 1.9(5) ?
C12 C6 C7 O2 . . . . -174.5(3) ?
C5 C6 C7 O2 . . . . 5.7(6) ?
C12 C6 C7 C9 . . . . 5.5(5) ?
C5 C6 C7 C9 . . . . -174.3(4) ?
O2 C7 C9 C10 . . . . 178.1(4) ?
C6 C7 C9 C10 . . . . -1.9(5) ?
C7 C9 C10 C11 . . . . -2.6(6) ?
C9 C10 C11 C12 . . . . 3.5(6) ?
C7 C6 C12 C11 . . . . -4.6(6) ?
C5 C6 C12 C11 . . . . 175.2(3) ?
C7 C6 C12 C13 . . . . 170.5(3) ?
C5 C6 C12 C13 . . . . -9.6(4) ?
C10 C11 C12 C6 . . . . 0.1(6) ?
C10 C11 C12 C13 . . . . -173.8(4) ?
C5 O4 C13 C12 . . . . -32.1(3) ?
C5 O4 C13 C14 . . . . 83.9(3) ?
C6 C12 C13 O4 . . . . 25.2(4) ?
C11 C12 C13 O4 . . . . -160.3(4) ?
C6 C12 C13 C14 . . . . -93.0(3) ?
C11 C12 C13 C14 . . . . 81.6(5) ?
O4 C13 C14 C15 . . . . 145.8(3) ?
C12 C13 C14 C15 . . . . -101.7(4) ?
O4 C13 C14 C20 . . . . -39.1(4) ?
C12 C13 C14 C20 . . . . 73.5(4) ?
C20 C14 C15 O3 . . . . 178.5(3) ?
C13 C14 C15 O3 . . . . -6.1(5) ?
C20 C14 C15 C16 . . . . -2.6(5) ?
C13 C14 C15 C16 . . . . 172.8(3) ?
O3 C15 C16 C17 . . . . -179.6(3) ?
C14 C15 C16 C17 . . . . 1.5(6) ?
C15 C16 C17 C18 . . . . 1.1(6) ?
C16 C17 C18 C19 . . . . 177.2(4) ?
C16 C17 C18 C20 . . . . -2.5(6) ?
C3 C2 C19 C18 . . . . -1.8(6) ?
C1 C2 C19 C18 . . . . 179.8(4) ?
C17 C18 C19 C2 . . . . -178.9(3) ?
C20 C18 C19 C2 . . . . 0.7(6) ?
C3 C4 C20 C18 . . . . -0.7(5) ?
O1 C4 C20 C18 . . . . -176.2(3) ?
C3 C4 C20 C14 . . . . 177.9(3) ?
O1 C4 C20 C14 . . . . 2.5(6) ?
C19 C18 C20 C4 . . . . 0.5(5) ?
C17 C18 C20 C4 . . . . -179.8(3) ?
C19 C18 C20 C14 . . . . -178.3(3) ?
C17 C18 C20 C14 . . . . 1.3(5) ?
C15 C14 C20 C4 . . . . -177.6(3) ?
C13 C14 C20 C4 . . . . 7.4(6) ?
C15 C14 C20 C18 . . . . 1.1(5) ?
C13 C14 C20 C18 . . . . -174.0(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O1 4_564 0.98 2.32 3.040(4) 130.1 ?
O3 H3A O2 4_564 0.98 2.19 2.977(4) 136.7 ?
C3 H12 O3 4_565 0.95 2.46 3.206(5) 135.2 ?
C9 H15 O4 1_655 0.95 2.43 3.199(4) 138.4 ?
C16 H6 O2 4_564 0.95 2.58 3.262(5) 128.6 ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH and CH2Cl2'
_chemical_compound_source        Actinomyces
