# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_fwxm28
_database_code_depnum_ccdc_archive 'CCDC 2150317'
loop_
_audit_author_name
_audit_author_address
'Xing-de Wu'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-02-06 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H28 O'
_chemical_formula_sum            'C20 H28 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         284.42
_chemical_absolute_configuration ad

_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                   10.0477(2)
_cell_length_b                   7.16210(10)
_cell_length_c                   11.3732(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.8680(10)
_cell_angle_gamma                90
_cell_volume                     818.01(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      3.8888
_cell_measurement_theta_max      72.3347
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312

_exptl_absorpt_coefficient_mu    0.518
_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  0.72
_exptl_absorpt_correction_T_max  0.90

_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            12142
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_theta_min         3.89
_diffrn_reflns_theta_max         72.33
_diffrn_reflns_theta_full        72.33
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3212
_reflns_number_gt                3196
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0842
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         3212
_refine_ls_number_parameters     194
_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)+(0.0526P)²+0.1357P] 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         0.211
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1450 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(8)

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 0.41396(13) 0.5993(2) -0.09962(11) 0.0255(3) Uani d . . . 1 . .
C C1 0.33142(16) 0.3858(2) 0.57718(14) 0.0149(3) Uani d . . . 1 . .
H H1 0.265539 0.317674 0.623771 0.018 Uiso calc U . R 1 . .
H H27 0.418326 0.321336 0.585936 0.018 Uiso calc U . R 1 . .
C C2 0.28516(14) 0.3933(2) 0.44562(13) 0.0113(3) Uani d . . . 1 . .
H H4 0.353187 0.329561 0.397476 0.014 Uiso calc U . R 1 . .
C C3 0.14871(15) 0.3121(2) 0.41407(14) 0.0125(3) Uani d . . . 1 . .
C C4 0.12043(16) 0.2415(2) 0.30791(15) 0.0152(3) Uani d . . . 1 . .
H H26 0.031307 0.201633 0.292982 0.018 Uiso calc U . R 1 . .
C C5 0.21578(16) 0.2182(2) 0.20839(14) 0.0149(3) Uani d . . . 1 . .
H H25 0.183171 0.115901 0.156482 0.018 Uiso calc U . R 1 . .
H H8 0.30395 0.1807 0.241896 0.018 Uiso calc U . R 1 . .
C C6 0.23282(15) 0.3956(2) 0.13368(13) 0.0126(3) Uani d . . . 1 . .
H H24 0.142213 0.445191 0.112242 0.015 Uiso calc U . R 1 . .
C C7 0.30717(15) 0.3608(2) 0.01837(14) 0.0136(3) Uani d . . . 1 . .
H H23 0.37753 0.265323 0.036499 0.016 Uiso calc U . R 1 . .
C C8 0.22996(16) 0.2943(3) -0.09316(14) 0.0165(3) Uani d . . . 1 . .
H H12 0.290673 0.313894 -0.16001 0.02 Uiso calc U . R 1 . .
C C9 0.10536(19) 0.4107(4) -0.12138(17) 0.0303(5) Uani d . . . 1 . .
H H13 0.073125 0.384113 -0.201892 0.045 Uiso calc U . R 1 . .
H H14 0.127121 0.543719 -0.114173 0.045 Uiso calc U . R 1 . .
H H2 0.036001 0.378983 -0.06616 0.045 Uiso calc U . R 1 . .
C C10 0.34383(17) 0.5898(2) 0.61956(15) 0.0184(4) Uani d . . . 1 . .
H H28 0.277625 0.617293 0.679774 0.022 Uiso calc U . R 1 . .
H H3 0.434138 0.614631 0.653362 0.022 Uiso calc U . R 1 . .
C C11 0.04369(16) 0.3293(2) 0.50514(15) 0.0177(3) Uani d . . . 1 . .
H H5 -0.043953 0.302285 0.468762 0.027 Uiso calc U . R 1 . .
H H6 0.044243 0.456518 0.536888 0.027 Uiso calc U . R 1 . .
H H7 0.062522 0.240276 0.568966 0.027 Uiso calc U . R 1 . .
C C12 0.1967(2) 0.0869(3) -0.09252(16) 0.0268(4) Uani d . . . 1 . .
H H9 0.130301 0.062214 -0.033264 0.04 Uiso calc U . R 1 . .
H H10 0.277635 0.014972 -0.073632 0.04 Uiso calc U . R 1 . .
H H11 0.160931 0.049896 -0.170251 0.04 Uiso calc U . R 1 . .
C C13 0.37889(15) 0.5460(2) -0.00397(14) 0.0162(3) Uani d . . . 1 . .
C C14 0.39785(16) 0.6475(2) 0.10791(14) 0.0159(3) Uani d . . . 1 . .
H H15 0.409857 0.786071 0.108814 0.019 Uiso calc U . R 1 . .
C C15 0.31209(15) 0.5514(2) 0.19838(14) 0.0123(3) Uani d . . . 1 . .
C C16 0.24822(16) 0.6664(2) 0.29458(14) 0.0136(3) Uani d . . . 1 . .
H H17 0.275559 0.798448 0.286435 0.016 Uiso calc U . R 1 . .
H H16 0.150197 0.660782 0.283201 0.016 Uiso calc U . R 1 . .
C C17 0.28535(14) 0.6008(2) 0.41699(14) 0.0117(3) Uani d . . . 1 . .
C C18 0.31742(15) 0.7053(2) 0.51060(14) 0.0130(3) Uani d . . . 1 . .
C C19 0.32591(17) 0.9146(2) 0.51841(15) 0.0178(4) Uani d . . . 1 . .
H H18 0.299754 0.969339 0.442137 0.027 Uiso calc U . R 1 . .
H H19 0.417522 0.951362 0.539645 0.027 Uiso calc U . R 1 . .
H H20 0.265993 0.95951 0.578542 0.027 Uiso calc U . R 1 . .
C C20 0.45956(15) 0.5257(2) 0.20635(14) 0.0149(3) Uani d . . . 1 . .
H H22 0.495612 0.402406 0.184333 0.018 Uiso calc U . R 1 . .
H H21 0.509345 0.58946 0.271303 0.018 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 C13 . 1.216(2) ?
C1 C10 . 1.542(2) ?
C1 C2 . 1.553(2) ?
C1 H1 . 0.99 ?
C1 H27 . 0.99 ?
C2 C17 . 1.521(2) ?
C2 C3 . 1.521(2) ?
C2 H4 . 1.0 ?
C3 C4 . 1.331(2) ?
C3 C11 . 1.507(2) ?
C4 C5 . 1.516(2) ?
C4 H26 . 0.95 ?
C5 C6 . 1.541(2) ?
C5 H25 . 0.99 ?
C5 H8 . 0.99 ?
C6 C15 . 1.544(2) ?
C6 C7 . 1.551(2) ?
C6 H24 . 1.0 ?
C7 C13 . 1.535(2) ?
C7 C8 . 1.540(2) ?
C7 H23 . 1.0 ?
C8 C12 . 1.523(3) ?
C8 C9 . 1.529(3) ?
C8 H12 . 1.0 ?
C9 H13 . 0.98 ?
C9 H14 . 0.98 ?
C9 H2 . 0.98 ?
C10 C18 . 1.506(2) ?
C10 H28 . 0.99 ?
C10 H3 . 0.99 ?
C11 H5 . 0.98 ?
C11 H6 . 0.98 ?
C11 H7 . 0.98 ?
C12 H9 . 0.98 ?
C12 H10 . 0.98 ?
C12 H11 . 0.98 ?
C13 C14 . 1.472(2) ?
C14 C15 . 1.527(2) ?
C14 C20 . 1.534(2) ?
C14 H15 . 1.0 ?
C15 C20 . 1.493(2) ?
C15 C16 . 1.528(2) ?
C16 C17 . 1.505(2) ?
C16 H17 . 0.99 ?
C16 H16 . 0.99 ?
C17 C18 . 1.332(2) ?
C18 C19 . 1.504(2) ?
C19 H18 . 0.98 ?
C19 H19 . 0.98 ?
C19 H20 . 0.98 ?
C20 H22 . 0.99 ?
C20 H21 . 0.99 ?

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
C10 C1 C2 . . 106.68(13) ?
C10 C1 H1 . . 110.4 ?
C2 C1 H1 . . 110.4 ?
C10 C1 H27 . . 110.4 ?
C2 C1 H27 . . 110.4 ?
H1 C1 H27 . . 108.6 ?
C17 C2 C3 . . 109.29(12) ?
C17 C2 C1 . . 103.74(12) ?
C3 C2 C1 . . 116.94(13) ?
C17 C2 H4 . . 108.9 ?
C3 C2 H4 . . 108.9 ?
C1 C2 H4 . . 108.9 ?
C4 C3 C11 . . 121.38(14) ?
C4 C3 C2 . . 121.54(14) ?
C11 C3 C2 . . 116.90(14) ?
C3 C4 C5 . . 126.71(15) ?
C3 C4 H26 . . 116.6 ?
C5 C4 H26 . . 116.6 ?
C4 C5 C6 . . 113.90(13) ?
C4 C5 H25 . . 108.8 ?
C6 C5 H25 . . 108.8 ?
C4 C5 H8 . . 108.8 ?
C6 C5 H8 . . 108.8 ?
H25 C5 H8 . . 107.7 ?
C5 C6 C15 . . 113.45(12) ?
C5 C6 C7 . . 113.52(13) ?
C15 C6 C7 . . 105.31(12) ?
C5 C6 H24 . . 108.1 ?
C15 C6 H24 . . 108.1 ?
C7 C6 H24 . . 108.1 ?
C13 C7 C8 . . 110.93(13) ?
C13 C7 C6 . . 104.04(13) ?
C8 C7 C6 . . 120.17(13) ?
C13 C7 H23 . . 107.0 ?
C8 C7 H23 . . 107.0 ?
C6 C7 H23 . . 107.0 ?
C12 C8 C9 . . 110.78(17) ?
C12 C8 C7 . . 113.70(15) ?
C9 C8 C7 . . 113.03(15) ?
C12 C8 H12 . . 106.2 ?
C9 C8 H12 . . 106.2 ?
C7 C8 H12 . . 106.2 ?
C8 C9 H13 . . 109.5 ?
C8 C9 H14 . . 109.5 ?
H13 C9 H14 . . 109.5 ?
C8 C9 H2 . . 109.5 ?
H13 C9 H2 . . 109.5 ?
H14 C9 H2 . . 109.5 ?
C18 C10 C1 . . 104.65(13) ?
C18 C10 H28 . . 110.8 ?
C1 C10 H28 . . 110.8 ?
C18 C10 H3 . . 110.8 ?
C1 C10 H3 . . 110.8 ?
H28 C10 H3 . . 108.9 ?
C3 C11 H5 . . 109.5 ?
C3 C11 H6 . . 109.5 ?
H5 C11 H6 . . 109.5 ?
C3 C11 H7 . . 109.5 ?
H5 C11 H7 . . 109.5 ?
H6 C11 H7 . . 109.5 ?
C8 C12 H9 . . 109.5 ?
C8 C12 H10 . . 109.5 ?
H9 C12 H10 . . 109.5 ?
C8 C12 H11 . . 109.5 ?
H9 C12 H11 . . 109.5 ?
H10 C12 H11 . . 109.5 ?
O1 C13 C14 . . 125.84(16) ?
O1 C13 C7 . . 124.79(16) ?
C14 C13 C7 . . 109.37(13) ?
C13 C14 C15 . . 107.46(13) ?
C13 C14 C20 . . 112.85(15) ?
C15 C14 C20 . . 58.37(10) ?
C13 C14 H15 . . 120.7 ?
C15 C14 H15 . . 120.7 ?
C20 C14 H15 . . 120.7 ?
C20 C15 C14 . . 61.04(10) ?
C20 C15 C16 . . 117.53(13) ?
C14 C15 C16 . . 119.93(13) ?
C20 C15 C6 . . 115.83(13) ?
C14 C15 C6 . . 107.35(13) ?
C16 C15 C6 . . 120.59(13) ?
C17 C16 C15 . . 113.38(13) ?
C17 C16 H17 . . 108.9 ?
C15 C16 H17 . . 108.9 ?
C17 C16 H16 . . 108.9 ?
C15 C16 H16 . . 108.9 ?
H17 C16 H16 . . 107.7 ?
C18 C17 C16 . . 127.58(15) ?
C18 C17 C2 . . 112.32(14) ?
C16 C17 C2 . . 120.08(14) ?
C17 C18 C19 . . 128.25(15) ?
C17 C18 C10 . . 112.35(14) ?
C19 C18 C10 . . 119.39(14) ?
C18 C19 H18 . . 109.5 ?
C18 C19 H19 . . 109.5 ?
H18 C19 H19 . . 109.5 ?
C18 C19 H20 . . 109.5 ?
H18 C19 H20 . . 109.5 ?
H19 C19 H20 . . 109.5 ?
C15 C20 C14 . . 60.59(10) ?
C15 C20 H22 . . 117.7 ?
C14 C20 H22 . . 117.7 ?
C15 C20 H21 . . 117.7 ?
C14 C20 H21 . . 117.7 ?
H22 C20 H21 . . 114.8 ?

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
C10 C1 C2 C17 . . . . 4.79(16) ?
C10 C1 C2 C3 . . . . -115.59(15) ?
C17 C2 C3 C4 . . . . 90.42(18) ?
C1 C2 C3 C4 . . . . -152.18(15) ?
C17 C2 C3 C11 . . . . -84.81(16) ?
C1 C2 C3 C11 . . . . 32.6(2) ?
C11 C3 C4 C5 . . . . 179.40(16) ?
C2 C3 C4 C5 . . . . 4.4(3) ?
C3 C4 C5 C6 . . . . -83.8(2) ?
C4 C5 C6 C15 . . . . 71.37(17) ?
C4 C5 C6 C7 . . . . -168.45(13) ?
C5 C6 C7 C13 . . . . -149.72(13) ?
C15 C6 C7 C13 . . . . -25.03(15) ?
C5 C6 C7 C8 . . . . 85.44(18) ?
C15 C6 C7 C8 . . . . -149.87(14) ?
C13 C7 C8 C12 . . . . 160.20(14) ?
C6 C7 C8 C12 . . . . -78.28(19) ?
C13 C7 C8 C9 . . . . -72.38(18) ?
C6 C7 C8 C9 . . . . 49.1(2) ?
C2 C1 C10 C18 . . . . -5.04(16) ?
C8 C7 C13 O1 . . . . -25.8(2) ?
C6 C7 C13 O1 . . . . -156.32(16) ?
C8 C7 C13 C14 . . . . 154.17(14) ?
C6 C7 C13 C14 . . . . 23.61(17) ?
O1 C13 C14 C15 . . . . 167.46(17) ?
C7 C13 C14 C15 . . . . -12.47(17) ?
O1 C13 C14 C20 . . . . -130.18(18) ?
C7 C13 C14 C20 . . . . 49.89(17) ?
C13 C14 C15 C20 . . . . 106.52(15) ?
C13 C14 C15 C16 . . . . -146.57(14) ?
C20 C14 C15 C16 . . . . 106.91(16) ?
C13 C14 C15 C6 . . . . -3.90(17) ?
C20 C14 C15 C6 . . . . -110.42(14) ?
C5 C6 C15 C20 . . . . 77.38(17) ?
C7 C6 C15 C20 . . . . -47.36(17) ?
C5 C6 C15 C14 . . . . 143.02(13) ?
C7 C6 C15 C14 . . . . 18.29(16) ?
C5 C6 C15 C16 . . . . -74.60(18) ?
C7 C6 C15 C16 . . . . 160.67(13) ?
C20 C15 C16 C17 . . . . -52.66(19) ?
C14 C15 C16 C17 . . . . -123.39(15) ?
C6 C15 C16 C17 . . . . 98.86(17) ?
C15 C16 C17 C18 . . . . 137.58(16) ?
C15 C16 C17 C2 . . . . -44.26(19) ?
C3 C2 C17 C18 . . . . 122.59(14) ?
C1 C2 C17 C18 . . . . -2.84(17) ?
C3 C2 C17 C16 . . . . -55.83(18) ?
C1 C2 C17 C16 . . . . 178.73(13) ?
C16 C17 C18 C19 . . . . -0.5(3) ?
C2 C17 C18 C19 . . . . -178.79(15) ?
C16 C17 C18 C10 . . . . 177.88(14) ?
C2 C17 C18 C10 . . . . -0.40(18) ?
C1 C10 C18 C17 . . . . 3.50(17) ?
C1 C10 C18 C19 . . . . -177.96(14) ?
C16 C15 C20 C14 . . . . -110.77(16) ?
C6 C15 C20 C14 . . . . 96.36(15) ?
C13 C14 C20 C15 . . . . -97.06(14) ?

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
C7 H23 O1 2_645 1.00 2.49 3.470(2) 165.2 ?

####################################################################### 
# 
# 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_fwxm76
_database_code_depnum_ccdc_archive 'CCDC 2150319'
loop_
_audit_author_name
_audit_author_address
'Xing-de Wu'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-02-06 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H30 O'
_chemical_formula_sum            'C20 H30 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         286.44
_chemical_absolute_configuration ad

_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                   10.8483(7)
_cell_length_b                   6.9259(4)
_cell_length_c                   11.4177(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.620(2)
_cell_angle_gamma                90
_cell_volume                     840.28(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      3.9527
_cell_measurement_theta_max      72.1926
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316

_exptl_absorpt_coefficient_mu    0.505
_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  0.67
_exptl_absorpt_correction_T_max  0.97

_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            11725
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_theta_min         3.95
_diffrn_reflns_theta_max         72.23
_diffrn_reflns_theta_full        72.23
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3271
_reflns_number_gt                3130
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1232
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         3271
_refine_ls_number_parameters     195
_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)+(0.0649P)²+0.1725P] 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         0.216
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.35(19)

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 0.45702(17) 0.3844(3) 0.54159(16) 0.0253(4) Uani d . . . 1 . .
C C1 -0.1028(2) 0.5846(5) 0.2046(3) 0.0359(7) Uani d . . . 1 . .
H H12 -0.128386 0.719993 0.185323 0.043 Uiso calc U . R 1 . .
H H1 -0.153674 0.498863 0.14418 0.043 Uiso calc U . R 1 . .
C C2 0.0397(2) 0.5576(4) 0.2066(2) 0.0230(5) Uani d . . . 1 . .
H H11 0.051756 0.426742 0.173523 0.028 Uiso calc U . R 1 . .
C C3 0.0986(2) 0.5560(3) 0.3400(2) 0.0198(5) Uani d . . . 1 . .
C C4 0.2381(2) 0.5708(4) 0.3871(2) 0.0198(5) Uani d . . . 1 . .
H H26 0.253092 0.564683 0.475504 0.024 Uiso calc U . R 1 . .
H H25 0.26604 0.699767 0.365569 0.024 Uiso calc U . R 1 . .
C C5 0.3228(2) 0.4170(3) 0.34376(19) 0.0168(5) Uani d . . . 1 . .
C C6 0.3719(2) 0.4736(3) 0.2299(2) 0.0175(5) Uani d . . . 1 . .
H H24 0.396491 0.612174 0.243494 0.021 Uiso calc U . R 1 . .
C C7 0.5000(2) 0.3672(4) 0.2377(2) 0.0200(5) Uani d . . . 1 . .
H H30 0.550787 0.442526 0.189553 0.024 Uiso calc U . R 1 . .
C C8 0.5068(2) 0.1517(4) 0.2036(2) 0.0229(5) Uani d . . . 1 . .
H H6 0.476112 0.0727 0.265258 0.027 Uiso calc U . R 1 . .
C C9 0.6447(2) 0.0966(4) 0.2062(2) 0.0300(6) Uani d . . . 1 . .
H H8 0.649732 -0.041014 0.18769 0.045 Uiso calc U . R 1 . .
H H2 0.695351 0.122597 0.285827 0.045 Uiso calc U . R 1 . .
H H7 0.676846 0.173088 0.146599 0.045 Uiso calc U . R 1 . .
C C10 0.4286(3) 0.0987(4) 0.0811(2) 0.0266(5) Uani d . . . 1 . .
H H4 0.451765 0.183115 0.020119 0.04 Uiso calc U . R 1 . .
H H5 0.339055 0.115065 0.081849 0.04 Uiso calc U . R 1 . .
H H3 0.444922 -0.035998 0.062845 0.04 Uiso calc U . R 1 . .
C C11 0.5577(2) 0.4006(4) 0.3709(2) 0.0221(5) Uani d . . . 1 . .
H H9 0.618079 0.296464 0.401874 0.027 Uiso calc U . R 1 . .
H H10 0.602403 0.525919 0.382237 0.027 Uiso calc U . R 1 . .
C C12 0.4479(2) 0.3997(4) 0.4350(2) 0.0186(5) Uani d . . . 1 . .
C C13 -0.1207(2) 0.5319(4) 0.3301(2) 0.0253(5) Uani d . . . 1 . .
H H13 -0.177003 0.625489 0.358702 0.03 Uiso calc U . R 1 . .
H H14 -0.156874 0.400836 0.331183 0.03 Uiso calc U . R 1 . .
C C14 0.0097(2) 0.5399(3) 0.4063(2) 0.0205(5) Uani d . . . 1 . .
C C15 0.0259(2) 0.5275(4) 0.5390(2) 0.0237(5) Uani d . . . 1 . .
H H17 0.114759 0.504953 0.574404 0.036 Uiso calc U . R 1 . .
H H16 -0.024865 0.420685 0.559832 0.036 Uiso calc U . R 1 . .
H H15 -0.00157 0.648788 0.569813 0.036 Uiso calc U . R 1 . .
C C16 0.0991(2) 0.7044(4) 0.1369(2) 0.0220(5) Uani d . . . 1 . .
C C17 0.0441(3) 0.9049(4) 0.1229(2) 0.0284(6) Uani d . . . 1 . .
H H19 0.099647 0.98977 0.088318 0.043 Uiso calc U . R 1 . .
H H20 0.035896 0.954582 0.201296 0.043 Uiso calc U . R 1 . .
H H18 -0.039016 0.900583 0.069861 0.043 Uiso calc U . R 1 . .
C C18 0.2031(2) 0.6631(4) 0.0954(2) 0.0215(5) Uani d . . . 1 . .
H H21 0.2345 0.762041 0.051774 0.026 Uiso calc U . R 1 . .
C C19 0.2752(2) 0.4762(4) 0.1108(2) 0.0199(5) Uani d . . . 1 . .
H H23 0.319342 0.459343 0.043598 0.024 Uiso calc U . R 1 . .
H H22 0.215812 0.367254 0.109145 0.024 Uiso calc U . R 1 . .
C C20 0.2606(2) 0.2174(4) 0.3415(2) 0.0214(5) Uani d . . . 1 . .
H H29 0.32002 0.117998 0.326905 0.032 Uiso calc U . R 1 . .
H H27 0.185283 0.213703 0.277634 0.032 Uiso calc U . R 1 . .
H H28 0.236862 0.193127 0.418598 0.032 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 C12 . 1.205(3) ?
C1 C13 . 1.529(4) ?
C1 C2 . 1.553(3) ?
C1 H12 . 0.99 ?
C1 H1 . 0.99 ?
C2 C16 . 1.513(3) ?
C2 C3 . 1.528(3) ?
C2 H11 . 1.0 ?
C3 C14 . 1.346(3) ?
C3 C4 . 1.504(3) ?
C4 C5 . 1.552(3) ?
C4 H26 . 0.99 ?
C4 H25 . 0.99 ?
C5 C20 . 1.536(3) ?
C5 C12 . 1.540(3) ?
C5 C6 . 1.552(3) ?
C6 C19 . 1.541(3) ?
C6 C7 . 1.559(3) ?
C6 H24 . 1.0 ?
C7 C11 . 1.541(3) ?
C7 C8 . 1.548(3) ?
C7 H30 . 1.0 ?
C8 C10 . 1.527(3) ?
C8 C9 . 1.539(3) ?
C8 H6 . 1.0 ?
C9 H8 . 0.98 ?
C9 H2 . 0.98 ?
C9 H7 . 0.98 ?
C10 H4 . 0.98 ?
C10 H5 . 0.98 ?
C10 H3 . 0.98 ?
C11 C12 . 1.519(3) ?
C11 H9 . 0.99 ?
C11 H10 . 0.99 ?
C13 C14 . 1.505(3) ?
C13 H13 . 0.99 ?
C13 H14 . 0.99 ?
C14 C15 . 1.491(3) ?
C15 H17 . 0.98 ?
C15 H16 . 0.98 ?
C15 H15 . 0.98 ?
C16 C18 . 1.339(4) ?
C16 C17 . 1.507(4) ?
C17 H19 . 0.98 ?
C17 H20 . 0.98 ?
C17 H18 . 0.98 ?
C18 C19 . 1.504(4) ?
C18 H21 . 0.95 ?
C19 H23 . 0.99 ?
C19 H22 . 0.99 ?
C20 H29 . 0.98 ?
C20 H27 . 0.98 ?
C20 H28 . 0.98 ?

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
C13 C1 C2 . . 105.8(2) ?
C13 C1 H12 . . 110.6 ?
C2 C1 H12 . . 110.6 ?
C13 C1 H1 . . 110.6 ?
C2 C1 H1 . . 110.6 ?
H12 C1 H1 . . 108.7 ?
C16 C2 C3 . . 113.1(2) ?
C16 C2 C1 . . 116.1(2) ?
C3 C2 C1 . . 103.3(2) ?
C16 C2 H11 . . 108.0 ?
C3 C2 H11 . . 108.0 ?
C1 C2 H11 . . 108.0 ?
C14 C3 C4 . . 126.0(2) ?
C14 C3 C2 . . 111.0(2) ?
C4 C3 C2 . . 123.0(2) ?
C3 C4 C5 . . 117.14(19) ?
C3 C4 H26 . . 108.0 ?
C5 C4 H26 . . 108.0 ?
C3 C4 H25 . . 108.0 ?
C5 C4 H25 . . 108.0 ?
H26 C4 H25 . . 107.3 ?
C20 C5 C12 . . 105.39(19) ?
C20 C5 C6 . . 115.93(19) ?
C12 C5 C6 . . 100.48(18) ?
C20 C5 C4 . . 109.70(19) ?
C12 C5 C4 . . 109.58(18) ?
C6 C5 C4 . . 114.80(19) ?
C19 C6 C5 . . 117.02(19) ?
C19 C6 C7 . . 119.79(19) ?
C5 C6 C7 . . 106.58(18) ?
C19 C6 H24 . . 103.8 ?
C5 C6 H24 . . 103.8 ?
C7 C6 H24 . . 103.8 ?
C11 C7 C8 . . 111.2(2) ?
C11 C7 C6 . . 99.56(18) ?
C8 C7 C6 . . 121.9(2) ?
C11 C7 H30 . . 107.8 ?
C8 C7 H30 . . 107.8 ?
C6 C7 H30 . . 107.8 ?
C10 C8 C9 . . 108.4(2) ?
C10 C8 C7 . . 114.6(2) ?
C9 C8 C7 . . 109.2(2) ?
C10 C8 H6 . . 108.1 ?
C9 C8 H6 . . 108.1 ?
C7 C8 H6 . . 108.1 ?
C8 C9 H8 . . 109.5 ?
C8 C9 H2 . . 109.5 ?
H8 C9 H2 . . 109.5 ?
C8 C9 H7 . . 109.5 ?
H8 C9 H7 . . 109.5 ?
H2 C9 H7 . . 109.5 ?
C8 C10 H4 . . 109.5 ?
C8 C10 H5 . . 109.5 ?
H4 C10 H5 . . 109.5 ?
C8 C10 H3 . . 109.5 ?
H4 C10 H3 . . 109.5 ?
H5 C10 H3 . . 109.5 ?
C12 C11 C7 . . 105.82(19) ?
C12 C11 H9 . . 110.6 ?
C7 C11 H9 . . 110.6 ?
C12 C11 H10 . . 110.6 ?
C7 C11 H10 . . 110.6 ?
H9 C11 H10 . . 108.7 ?
O1 C12 C11 . . 125.0(2) ?
O1 C12 C5 . . 124.9(2) ?
C11 C12 C5 . . 110.09(19) ?
C14 C13 C1 . . 104.5(2) ?
C14 C13 H13 . . 110.8 ?
C1 C13 H13 . . 110.8 ?
C14 C13 H14 . . 110.8 ?
C1 C13 H14 . . 110.8 ?
H13 C13 H14 . . 108.9 ?
C3 C14 C15 . . 128.7(2) ?
C3 C14 C13 . . 112.0(2) ?
C15 C14 C13 . . 119.3(2) ?
C14 C15 H17 . . 109.5 ?
C14 C15 H16 . . 109.5 ?
H17 C15 H16 . . 109.5 ?
C14 C15 H15 . . 109.5 ?
H17 C15 H15 . . 109.5 ?
H16 C15 H15 . . 109.5 ?
C18 C16 C17 . . 120.2(2) ?
C18 C16 C2 . . 121.4(2) ?
C17 C16 C2 . . 118.3(2) ?
C16 C17 H19 . . 109.5 ?
C16 C17 H20 . . 109.5 ?
H19 C17 H20 . . 109.5 ?
C16 C17 H18 . . 109.5 ?
H19 C17 H18 . . 109.5 ?
H20 C17 H18 . . 109.5 ?
C16 C18 C19 . . 126.7(2) ?
C16 C18 H21 . . 116.6 ?
C19 C18 H21 . . 116.6 ?
C18 C19 C6 . . 111.0(2) ?
C18 C19 H23 . . 109.4 ?
C6 C19 H23 . . 109.4 ?
C18 C19 H22 . . 109.4 ?
C6 C19 H22 . . 109.4 ?
H23 C19 H22 . . 108.0 ?
C5 C20 H29 . . 109.5 ?
C5 C20 H27 . . 109.5 ?
H29 C20 H27 . . 109.5 ?
C5 C20 H28 . . 109.5 ?
H29 C20 H28 . . 109.5 ?
H27 C20 H28 . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 C2 C16 . . . . -142.1(2) ?
C13 C1 C2 C3 . . . . -17.7(3) ?
C16 C2 C3 C14 . . . . 138.2(2) ?
C1 C2 C3 C14 . . . . 11.9(3) ?
C16 C2 C3 C4 . . . . -41.7(3) ?
C1 C2 C3 C4 . . . . -168.0(2) ?
C14 C3 C4 C5 . . . . 123.0(3) ?
C2 C3 C4 C5 . . . . -57.0(3) ?
C3 C4 C5 C20 . . . . -41.4(3) ?
C3 C4 C5 C12 . . . . -156.7(2) ?
C3 C4 C5 C6 . . . . 91.2(2) ?
C20 C5 C6 C19 . . . . 58.3(3) ?
C12 C5 C6 C19 . . . . 171.2(2) ?
C4 C5 C6 C19 . . . . -71.3(3) ?
C20 C5 C6 C7 . . . . -78.9(2) ?
C12 C5 C6 C7 . . . . 34.0(2) ?
C4 C5 C6 C7 . . . . 151.48(19) ?
C19 C6 C7 C11 . . . . -178.3(2) ?
C5 C6 C7 C11 . . . . -42.5(2) ?
C19 C6 C7 C8 . . . . -55.8(3) ?
C5 C6 C7 C8 . . . . 80.0(3) ?
C11 C7 C8 C10 . . . . 168.1(2) ?
C6 C7 C8 C10 . . . . 51.3(3) ?
C11 C7 C8 C9 . . . . -70.0(2) ?
C6 C7 C8 C9 . . . . 173.2(2) ?
C8 C7 C11 C12 . . . . -96.4(2) ?
C6 C7 C11 C12 . . . . 33.4(2) ?
C7 C11 C12 O1 . . . . 165.0(2) ?
C7 C11 C12 C5 . . . . -13.9(3) ?
C20 C5 C12 O1 . . . . -70.3(3) ?
C6 C5 C12 O1 . . . . 168.9(2) ?
C4 C5 C12 O1 . . . . 47.7(3) ?
C20 C5 C12 C11 . . . . 108.6(2) ?
C6 C5 C12 C11 . . . . -12.2(3) ?
C4 C5 C12 C11 . . . . -133.4(2) ?
C2 C1 C13 C14 . . . . 17.4(3) ?
C4 C3 C14 C15 . . . . -1.9(4) ?
C2 C3 C14 C15 . . . . 178.2(2) ?
C4 C3 C14 C13 . . . . 179.0(2) ?
C2 C3 C14 C13 . . . . -1.0(3) ?
C1 C13 C14 C3 . . . . -10.6(3) ?
C1 C13 C14 C15 . . . . 170.1(2) ?
C3 C2 C16 C18 . . . . 85.2(3) ?
C1 C2 C16 C18 . . . . -155.6(2) ?
C3 C2 C16 C17 . . . . -90.3(3) ?
C1 C2 C16 C17 . . . . 28.8(3) ?
C17 C16 C18 C19 . . . . 174.8(2) ?
C2 C16 C18 C19 . . . . -0.6(4) ?
C16 C18 C19 C6 . . . . -86.0(3) ?
C5 C6 C19 C18 . . . . 82.6(3) ?
C7 C6 C19 C18 . . . . -146.0(2) ?

####################################################################### 
# 
# 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_fwxm189
_database_code_depnum_ccdc_archive 'CCDC 2150318'
loop_
_audit_author_name
_audit_author_address
'Xing-de Wu'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-02-06 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H30 O4'
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         334.44
_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                   6.5674(2)
_cell_length_b                   15.9608(6)
_cell_length_c                   16.7628(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1757.09(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9460
_cell_measurement_theta_min      2.7685
_cell_measurement_theta_max      72.0861
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.770
_exptl_crystal_size_mid          0.620
_exptl_crystal_size_min          0.220
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    0.691
_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  0.67
_exptl_absorpt_correction_T_max  0.86

_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            19975
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_theta_min         5.28
_diffrn_reflns_theta_max         72.12
_diffrn_reflns_theta_full        72.12
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             3453
_reflns_number_gt                3446
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0732
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_number_reflns         3453
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+0.5421P] 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         0.455
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)

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 0.67423(19) 0.37528(8) 0.49099(8) 0.0177(3) Uani d . . . 1 . .
O O2 0.41531(19) 0.12258(7) 0.65622(7) 0.0143(3) Uani d . . . 1 . .
H H29 0.335189 0.125869 0.61729 0.021 Uiso calc U . R 1 . .
O O3 0.41843(17) 0.45650(7) 0.68930(6) 0.0110(2) Uani d . . . 1 . .
O O4 0.26685(19) 0.50975(7) 0.80413(7) 0.0157(3) Uani d . . . 1 . .
H H30 0.376455 0.535956 0.810796 0.024 Uiso calc U . R 1 . .
C C1 0.3079(3) 0.68253(10) 0.52031(11) 0.0193(4) Uani d . . . 1 . .
H H7 0.368126 0.670358 0.468098 0.029 Uiso calc U . R 1 . .
H H6 0.415329 0.699164 0.557653 0.029 Uiso calc U . R 1 . .
H H1 0.209104 0.728218 0.514978 0.029 Uiso calc U . R 1 . .
C C2 0.2001(3) 0.60416(10) 0.55188(10) 0.0145(3) Uani d . . . 1 . .
H H28 0.134524 0.619482 0.603714 0.017 Uiso calc U . R 1 . .
C C3 0.3589(2) 0.53621(10) 0.56941(10) 0.0108(3) Uani d . . . 1 . .
H H8 0.462873 0.564272 0.603868 0.013 Uiso calc U . R 1 . .
C C4 0.2910(2) 0.45625(10) 0.61781(9) 0.0098(3) Uani d . . . 1 . .
C C5 0.3557(2) 0.37986(10) 0.56622(9) 0.0101(3) Uani d . . . 1 . .
C C6 0.4117(3) 0.30284(10) 0.61184(10) 0.0113(3) Uani d . . . 1 . .
H H12 0.532193 0.27433 0.596178 0.014 Uiso calc U . R 1 . .
C C7 0.3066(3) 0.27066(10) 0.67280(9) 0.0107(3) Uani d . . . 1 . .
C C8 0.3704(3) 0.18820(10) 0.71221(10) 0.0114(3) Uani d . . . 1 . .
C C9 0.5666(3) 0.20030(11) 0.75932(11) 0.0154(4) Uani d . . . 1 . .
H H17 0.604553 0.147388 0.785 0.023 Uiso calc U . R 1 . .
H H18 0.545884 0.243395 0.800156 0.023 Uiso calc U . R 1 . .
H H2 0.67569 0.217886 0.723097 0.023 Uiso calc U . R 1 . .
C C10 0.0305(3) 0.57824(11) 0.49447(12) 0.0202(4) Uani d . . . 1 . .
H H3 -0.067041 0.624331 0.488867 0.03 Uiso calc U . R 1 . .
H H5 -0.03949 0.528718 0.51551 0.03 Uiso calc U . R 1 . .
H H4 0.089343 0.565054 0.442231 0.03 Uiso calc U . R 1 . .
C C11 0.4787(3) 0.50470(10) 0.49602(10) 0.0134(3) Uani d . . . 1 . .
H H27 0.394832 0.508745 0.447094 0.016 Uiso calc U . R 1 . .
H H26 0.604783 0.537735 0.488389 0.016 Uiso calc U . R 1 . .
C C12 0.5281(3) 0.41446(10) 0.51491(10) 0.0119(3) Uani d . . . 1 . .
C C13 0.1932(3) 0.35579(10) 0.50270(10) 0.0139(3) Uani d . . . 1 . .
H H11 0.253969 0.317755 0.463463 0.021 Uiso calc U . R 1 . .
H H10 0.145076 0.406526 0.475711 0.021 Uiso calc U . R 1 . .
H H9 0.078309 0.327938 0.528916 0.021 Uiso calc U . R 1 . .
C C14 0.1185(3) 0.30505(10) 0.71473(10) 0.0108(3) Uani d . . . 1 . .
H H13 -0.00129 0.288573 0.681392 0.013 Uiso calc U . R 1 . .
C C15 0.1071(3) 0.25204(10) 0.79188(10) 0.0132(3) Uani d . . . 1 . .
H H19 0.19266 0.276586 0.834513 0.016 Uiso calc U . R 1 . .
H H14 -0.034898 0.24757 0.811279 0.016 Uiso calc U . R 1 . .
C C16 0.1887(3) 0.16657(10) 0.76593(10) 0.0139(3) Uani d . . . 1 . .
H H15 0.08413 0.134755 0.736062 0.017 Uiso calc U . R 1 . .
H H16 0.232656 0.133135 0.812597 0.017 Uiso calc U . R 1 . .
C C17 0.0999(2) 0.40097(10) 0.72932(9) 0.0107(3) Uani d . . . 1 . .
C C18 0.0754(2) 0.45070(10) 0.65092(9) 0.0110(3) Uani d . . . 1 . .
H H20 -0.015618 0.420896 0.613353 0.013 Uiso calc U . R 1 . .
H H22 0.019236 0.507217 0.661315 0.013 Uiso calc U . R 1 . .
C C19 0.3040(3) 0.43716(10) 0.75882(10) 0.0109(3) Uani d . . . 1 . .
H H21 0.377779 0.394659 0.791779 0.013 Uiso calc U . R 1 . .
C C20 -0.0818(3) 0.41804(10) 0.78442(10) 0.0140(3) Uani d . . . 1 . .
H H23 -0.056447 0.392648 0.836717 0.021 Uiso calc U . R 1 . .
H H24 -0.205218 0.39374 0.761112 0.021 Uiso calc U . R 1 . .
H H25 -0.099755 0.47864 0.790647 0.021 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 C12 . 1.214(2) ?
O2 C8 . 1.4369(19) ?
O2 H29 . 0.84 ?
O3 C19 . 1.4205(19) ?
O3 C4 . 1.4616(19) ?
O4 C19 . 1.407(2) ?
O4 H30 . 0.84 ?
C1 C2 . 1.532(2) ?
C1 H7 . 0.98 ?
C1 H6 . 0.98 ?
C1 H1 . 0.98 ?
C2 C10 . 1.529(2) ?
C2 C3 . 1.533(2) ?
C2 H28 . 1.0 ?
C3 C11 . 1.544(2) ?
C3 C4 . 1.577(2) ?
C3 H8 . 1.0 ?
C4 C18 . 1.524(2) ?
C4 C5 . 1.554(2) ?
C5 C6 . 1.494(2) ?
C5 C12 . 1.525(2) ?
C5 C13 . 1.555(2) ?
C6 C7 . 1.336(2) ?
C6 H12 . 0.95 ?
C7 C14 . 1.524(2) ?
C7 C8 . 1.531(2) ?
C8 C9 . 1.524(2) ?
C8 C16 . 1.534(2) ?
C9 H17 . 0.98 ?
C9 H18 . 0.98 ?
C9 H2 . 0.98 ?
C10 H3 . 0.98 ?
C10 H5 . 0.98 ?
C10 H4 . 0.98 ?
C11 C12 . 1.510(2) ?
C11 H27 . 0.99 ?
C11 H26 . 0.99 ?
C13 H11 . 0.98 ?
C13 H10 . 0.98 ?
C13 H9 . 0.98 ?
C14 C15 . 1.547(2) ?
C14 C17 . 1.555(2) ?
C14 H13 . 1.0 ?
C15 C16 . 1.529(2) ?
C15 H19 . 0.99 ?
C15 H14 . 0.99 ?
C16 H15 . 0.99 ?
C16 H16 . 0.99 ?
C17 C20 . 1.533(2) ?
C17 C19 . 1.541(2) ?
C17 C18 . 1.544(2) ?
C18 H20 . 0.99 ?
C18 H22 . 0.99 ?
C19 H21 . 1.0 ?
C20 H23 . 0.98 ?
C20 H24 . 0.98 ?
C20 H25 . 0.98 ?

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 O2 H29 . . 109.5 ?
C19 O3 C4 . . 111.67(12) ?
C19 O4 H30 . . 109.5 ?
C2 C1 H7 . . 109.5 ?
C2 C1 H6 . . 109.5 ?
H7 C1 H6 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H7 C1 H1 . . 109.5 ?
H6 C1 H1 . . 109.5 ?
C10 C2 C1 . . 109.88(14) ?
C10 C2 C3 . . 115.14(14) ?
C1 C2 C3 . . 109.23(15) ?
C10 C2 H28 . . 107.4 ?
C1 C2 H28 . . 107.4 ?
C3 C2 H28 . . 107.4 ?
C2 C3 C11 . . 115.10(14) ?
C2 C3 C4 . . 118.60(14) ?
C11 C3 C4 . . 106.88(13) ?
C2 C3 H8 . . 105.0 ?
C11 C3 H8 . . 105.0 ?
C4 C3 H8 . . 105.0 ?
O3 C4 C18 . . 103.51(12) ?
O3 C4 C5 . . 107.59(12) ?
C18 C4 C5 . . 114.27(13) ?
O3 C4 C3 . . 104.94(12) ?
C18 C4 C3 . . 119.83(13) ?
C5 C4 C3 . . 105.75(12) ?
C6 C5 C12 . . 113.82(14) ?
C6 C5 C4 . . 115.35(13) ?
C12 C5 C4 . . 103.44(13) ?
C6 C5 C13 . . 108.43(13) ?
C12 C5 C13 . . 102.27(12) ?
C4 C5 C13 . . 112.79(13) ?
C7 C6 C5 . . 125.51(15) ?
C7 C6 H12 . . 117.2 ?
C5 C6 H12 . . 117.2 ?
C6 C7 C14 . . 129.29(15) ?
C6 C7 C8 . . 121.27(15) ?
C14 C7 C8 . . 109.43(13) ?
O2 C8 C9 . . 104.91(13) ?
O2 C8 C7 . . 113.64(13) ?
C9 C8 C7 . . 110.25(13) ?
O2 C8 C16 . . 112.27(13) ?
C9 C8 C16 . . 112.47(14) ?
C7 C8 C16 . . 103.51(13) ?
C8 C9 H17 . . 109.5 ?
C8 C9 H18 . . 109.5 ?
H17 C9 H18 . . 109.5 ?
C8 C9 H2 . . 109.5 ?
H17 C9 H2 . . 109.5 ?
H18 C9 H2 . . 109.5 ?
C2 C10 H3 . . 109.5 ?
C2 C10 H5 . . 109.5 ?
H3 C10 H5 . . 109.5 ?
C2 C10 H4 . . 109.5 ?
H3 C10 H4 . . 109.5 ?
H5 C10 H4 . . 109.5 ?
C12 C11 C3 . . 104.65(13) ?
C12 C11 H27 . . 110.8 ?
C3 C11 H27 . . 110.8 ?
C12 C11 H26 . . 110.8 ?
C3 C11 H26 . . 110.8 ?
H27 C11 H26 . . 108.9 ?
O1 C12 C11 . . 126.31(16) ?
O1 C12 C5 . . 125.93(15) ?
C11 C12 C5 . . 107.71(13) ?
C5 C13 H11 . . 109.5 ?
C5 C13 H10 . . 109.5 ?
H11 C13 H10 . . 109.5 ?
C5 C13 H9 . . 109.5 ?
H11 C13 H9 . . 109.5 ?
H10 C13 H9 . . 109.5 ?
C7 C14 C15 . . 103.16(13) ?
C7 C14 C17 . . 119.39(13) ?
C15 C14 C17 . . 113.77(13) ?
C7 C14 H13 . . 106.6 ?
C15 C14 H13 . . 106.6 ?
C17 C14 H13 . . 106.6 ?
C16 C15 C14 . . 103.48(13) ?
C16 C15 H19 . . 111.1 ?
C14 C15 H19 . . 111.1 ?
C16 C15 H14 . . 111.1 ?
C14 C15 H14 . . 111.1 ?
H19 C15 H14 . . 109.0 ?
C15 C16 C8 . . 103.83(13) ?
C15 C16 H15 . . 111.0 ?
C8 C16 H15 . . 111.0 ?
C15 C16 H16 . . 111.0 ?
C8 C16 H16 . . 111.0 ?
H15 C16 H16 . . 109.0 ?
C20 C17 C19 . . 114.65(13) ?
C20 C17 C18 . . 109.90(13) ?
C19 C17 C18 . . 99.86(12) ?
C20 C17 C14 . . 109.31(13) ?
C19 C17 C14 . . 110.56(13) ?
C18 C17 C14 . . 112.36(13) ?
C4 C18 C17 . . 104.07(13) ?
C4 C18 H20 . . 110.9 ?
C17 C18 H20 . . 110.9 ?
C4 C18 H22 . . 110.9 ?
C17 C18 H22 . . 110.9 ?
H20 C18 H22 . . 109.0 ?
O4 C19 O3 . . 110.84(12) ?
O4 C19 C17 . . 109.33(13) ?
O3 C19 C17 . . 106.16(12) ?
O4 C19 H21 . . 110.1 ?
O3 C19 H21 . . 110.1 ?
C17 C19 H21 . . 110.1 ?
C17 C20 H23 . . 109.5 ?
C17 C20 H24 . . 109.5 ?
H23 C20 H24 . . 109.5 ?
C17 C20 H25 . . 109.5 ?
H23 C20 H25 . . 109.5 ?
H24 C20 H25 . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C2 C3 C11 . . . . 60.9(2) ?
C1 C2 C3 C11 . . . . -63.29(19) ?
C10 C2 C3 C4 . . . . -67.5(2) ?
C1 C2 C3 C4 . . . . 168.36(14) ?
C19 O3 C4 C18 . . . . 10.20(16) ?
C19 O3 C4 C5 . . . . -111.10(14) ?
C19 O3 C4 C3 . . . . 136.61(13) ?
C2 C3 C4 O3 . . . . -119.78(15) ?
C11 C3 C4 O3 . . . . 108.13(14) ?
C2 C3 C4 C18 . . . . -4.2(2) ?
C11 C3 C4 C18 . . . . -136.30(14) ?
C2 C3 C4 C5 . . . . 126.63(15) ?
C11 C3 C4 C5 . . . . -5.45(16) ?
O3 C4 C5 C6 . . . . 37.03(18) ?
C18 C4 C5 C6 . . . . -77.28(18) ?
C3 C4 C5 C6 . . . . 148.76(14) ?
O3 C4 C5 C12 . . . . -87.91(14) ?
C18 C4 C5 C12 . . . . 157.79(13) ?
C3 C4 C5 C12 . . . . 23.83(15) ?
O3 C4 C5 C13 . . . . 162.37(12) ?
C18 C4 C5 C13 . . . . 48.06(18) ?
C3 C4 C5 C13 . . . . -85.90(15) ?
C12 C5 C6 C7 . . . . 165.05(16) ?
C4 C5 C6 C7 . . . . 45.7(2) ?
C13 C5 C6 C7 . . . . -81.9(2) ?
C5 C6 C7 C14 . . . . -4.7(3) ?
C5 C6 C7 C8 . . . . 176.17(15) ?
C6 C7 C8 O2 . . . . -47.0(2) ?
C14 C7 C8 O2 . . . . 133.70(14) ?
C6 C7 C8 C9 . . . . 70.40(19) ?
C14 C7 C8 C9 . . . . -108.86(15) ?
C6 C7 C8 C16 . . . . -169.08(15) ?
C14 C7 C8 C16 . . . . 11.66(17) ?
C2 C3 C11 C12 . . . . -149.35(14) ?
C4 C3 C11 C12 . . . . -15.37(17) ?
C3 C11 C12 O1 . . . . -151.30(17) ?
C3 C11 C12 C5 . . . . 31.46(17) ?
C6 C5 C12 O1 . . . . 22.1(2) ?
C4 C5 C12 O1 . . . . 147.98(16) ?
C13 C5 C12 O1 . . . . -94.66(18) ?
C6 C5 C12 C11 . . . . -160.69(13) ?
C4 C5 C12 C11 . . . . -34.77(16) ?
C13 C5 C12 C11 . . . . 82.60(15) ?
C6 C7 C14 C15 . . . . -165.76(17) ?
C8 C7 C14 C15 . . . . 13.42(16) ?
C6 C7 C14 C17 . . . . -38.4(2) ?
C8 C7 C14 C17 . . . . 140.78(14) ?
C7 C14 C15 C16 . . . . -33.45(16) ?
C17 C14 C15 C16 . . . . -164.27(14) ?
C14 C15 C16 C8 . . . . 41.53(16) ?
O2 C8 C16 C15 . . . . -155.48(13) ?
C9 C8 C16 C15 . . . . 86.46(16) ?
C7 C8 C16 C15 . . . . -32.53(16) ?
C7 C14 C17 C20 . . . . -170.31(14) ?
C15 C14 C17 C20 . . . . -48.06(18) ?
C7 C14 C17 C19 . . . . -43.20(19) ?
C15 C14 C17 C19 . . . . 79.05(17) ?
C7 C14 C17 C18 . . . . 67.41(19) ?
C15 C14 C17 C18 . . . . -170.34(14) ?
O3 C4 C18 C17 . . . . -30.45(15) ?
C5 C4 C18 C17 . . . . 86.24(15) ?
C3 C4 C18 C17 . . . . -146.76(14) ?
C20 C17 C18 C4 . . . . 158.68(13) ?
C19 C17 C18 C4 . . . . 37.81(15) ?
C14 C17 C18 C4 . . . . -79.38(16) ?
C4 O3 C19 O4 . . . . -104.29(14) ?
C4 O3 C19 C17 . . . . 14.33(16) ?
C20 C17 C19 O4 . . . . -29.75(18) ?
C18 C17 C19 O4 . . . . 87.63(14) ?
C14 C17 C19 O4 . . . . -153.85(13) ?
C20 C17 C19 O3 . . . . -149.36(13) ?
C18 C17 C19 O3 . . . . -31.98(15) ?
C14 C17 C19 O3 . . . . 86.54(15) ?

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
O2 H29 O1 2_456 0.84 2.10 2.9322(17) 170.4 ?
O4 H30 O2 3_656 0.84 2.02 2.8358(17) 163.1 ?
C11 H27 O4 4_564 0.99 2.64 3.606(2) 165.8 ?

