# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

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

data_exp_6254
_database_code_depnum_ccdc_archive 'CCDC 2015764'
loop_
_audit_author_name
_audit_author_address
'archromone A'
;Peking Union Medical College
China
;
_audit_update_record             
;
2020-07-12 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_audit_creation_date             2019-12-09
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H18 O5, H2 O'
_chemical_formula_sum            'C16 H20 O6'
_chemical_formula_weight         308.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'

_cell_length_a                   8.1628(6)
_cell_length_b                   13.0501(8)
_cell_length_c                   13.9274(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.346(8)
_cell_angle_gamma                90.00
_cell_volume                     1443.55(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2479
_cell_measurement_temperature    111.95(10)
_cell_measurement_theta_max      70.9840
_cell_measurement_theta_min      5.5470
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4617
_diffrn_reflns_theta_full        71.17
_diffrn_reflns_theta_max         71.17
_diffrn_reflns_theta_min         6.52
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9719
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   26.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  131.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  140.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  151.00  176.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  131.00  175.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   93.00  118.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   92.00  117.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   94.00  122.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega   93.00  150.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
 10 omega   94.00  119.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   92.00  123.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 12 omega   91.00  117.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   87.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 14 omega   91.00  175.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
 15 omega   62.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   13.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 17 omega   50.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  102.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
 19 omega   65.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   42.00   67.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   96.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 22 omega    8.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 23 omega  -32.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
 24 omega  -25.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919    0.0000 -120.0000 109

#__ type_ start__ end____ width___ exp.time_
 25 omega   40.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 26 omega   42.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 27 omega   63.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 28 omega   59.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -90.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1418716000
_diffrn_orient_matrix_UB_12      -0.0080371000
_diffrn_orient_matrix_UB_13      0.0943036000
_diffrn_orient_matrix_UB_21      -0.0839637000
_diffrn_orient_matrix_UB_22      -0.0964185000
_diffrn_orient_matrix_UB_23      0.0309898000
_diffrn_orient_matrix_UB_31      0.1022537000
_diffrn_orient_matrix_UB_32      -0.0679302000
_diffrn_orient_matrix_UB_33      -0.0553312000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2644
_reflns_number_total             2729
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.3276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0948
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.2279(2) 0.14187(13) 0.65795(13) 0.0152(4) Uani 1 1 d . . .
H13A H 0.1102 0.1352 0.6245 0.018 Uiso 1 1 calc R . .
H13B H 0.2904 0.0898 0.6317 0.018 Uiso 1 1 calc R . .
C14 C 0.2462(2) 0.12278(13) 0.76684(13) 0.0129(3) Uani 1 1 d . . .
C7 C 0.2120(2) 0.32830(13) 0.69326(13) 0.0128(3) Uani 1 1 d . . .
H7 H 0.0901 0.3169 0.6749 0.015 Uiso 1 1 calc R . .
O2 O 0.33518(16) -0.05469(10) 0.74886(9) 0.0152(3) Uani 1 1 d . . .
H2 H 0.4329 -0.0345 0.7607 0.023 Uiso 1 1 calc R . .
C4 C 0.2610(2) 0.18184(14) 0.93680(13) 0.0148(4) Uani 1 1 d . . .
O1 O 0.29457(17) 0.25069(11) 0.99816(10) 0.0200(3) Uani 1 1 d . . .
C8 C 0.2414(2) 0.43651(13) 0.65968(14) 0.0143(4) Uani 1 1 d . . .
O4 O 0.15306(16) 0.52888(10) 0.78684(9) 0.0169(3) Uani 1 1 d . . .
O5 O 0.34366(16) 0.59984(10) 0.71518(10) 0.0181(3) Uani 1 1 d . . .
H5 H 0.3442 0.6442 0.7570 0.027 Uiso 1 1 calc R . .
O3 O 0.43116(17) 0.35612(11) 0.84035(9) 0.0182(3) Uani 1 1 d . . .
H3 H 0.4664 0.3411 0.8986 0.027 Uiso 1 1 calc R . .
C12 C 0.2912(2) 0.24850(14) 0.63533(12) 0.0134(3) Uani 1 1 d . . .
C2 C 0.2941(2) -0.00344(14) 0.90805(14) 0.0167(4) Uani 1 1 d . . .
H2A H 0.4156 0.0032 0.9282 0.020 Uiso 1 1 calc R . .
H2B H 0.2640 -0.0717 0.9255 0.020 Uiso 1 1 calc R . .
C10 C 0.2244(2) 0.36902(15) 0.49399(13) 0.0186(4) Uani 1 1 d . . .
H10 H 0.2003 0.3831 0.4267 0.022 Uiso 1 1 calc R . .
C15 C 0.2423(2) 0.52506(14) 0.72731(13) 0.0143(3) Uani 1 1 d . . .
C5 C 0.2612(2) 0.20014(14) 0.83183(13) 0.0127(3) Uani 1 1 d . . .
C1 C 0.2374(2) 0.01098(13) 0.79691(12) 0.0134(3) Uani 1 1 d . . .
H1 H 0.1197 -0.0109 0.7766 0.016 Uiso 1 1 calc R . .
C6 C 0.2664(2) 0.31252(14) 0.80471(13) 0.0136(3) Uani 1 1 d . . .
H6 H 0.1874 0.3497 0.8354 0.016 Uiso 1 1 calc R . .
C11 C 0.2391(2) 0.27253(14) 0.52565(13) 0.0163(4) Uani 1 1 d . . .
H11 H 0.2171 0.2192 0.4802 0.020 Uiso 1 1 calc R . .
C16 C 0.4862(2) 0.24842(15) 0.66296(13) 0.0172(3) Uani 1 1 d . . .
H16A H 0.5252 0.2280 0.7306 0.026 Uiso 1 1 calc R . .
H16B H 0.5268 0.3160 0.6542 0.026 Uiso 1 1 calc R . .
H16C H 0.5274 0.2012 0.6212 0.026 Uiso 1 1 calc R . .
C9 C 0.2465(2) 0.45323(15) 0.56590(14) 0.0175(4) Uani 1 1 d . . .
H9 H 0.2644 0.5194 0.5457 0.021 Uiso 1 1 calc R . .
C3 C 0.2118(3) 0.07603(14) 0.96231(14) 0.0187(4) Uani 1 1 d . . .
H3A H 0.0904 0.0687 0.9434 0.022 Uiso 1 1 calc R . .
H3B H 0.2479 0.0652 1.0330 0.022 Uiso 1 1 calc R . .
O6 O -0.13514(17) 0.24940(11) 0.83853(10) 0.0188(3) Uani 1 1 d D . .
H6A H -0.147(3) 0.3063(13) 0.8079(18) 0.028 Uiso 1 1 d D . .
H6B H -0.198(3) 0.250(2) 0.8794(15) 0.028 Uiso 1 1 d D . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.510(2) . ?
C13 C12 1.542(2) . ?
C14 C5 1.343(3) . ?
C14 C1 1.524(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.524(2) . ?
C7 C12 1.548(2) . ?
C7 C6 1.527(2) . ?
O2 H2 0.8200 . ?
O2 C1 1.437(2) . ?
C4 O1 1.227(2) . ?
C4 C5 1.481(2) . ?
C4 C3 1.503(2) . ?
C8 C15 1.490(2) . ?
C8 C9 1.334(3) . ?
O4 C15 1.225(2) . ?
O5 H5 0.8200 . ?
O5 C15 1.315(2) . ?
O3 H3 0.8200 . ?
O3 C6 1.439(2) . ?
C12 C11 1.521(2) . ?
C12 C16 1.548(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.521(2) . ?
C2 C3 1.527(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.330(3) . ?
C10 C9 1.470(3) . ?
C5 C6 1.517(2) . ?
C1 H1 0.9800 . ?
C6 H6 0.9800 . ?
C11 H11 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C9 H9 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O6 H6A 0.851(10) . ?
O6 H6B 0.849(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C14 C13 C12 113.21(14) . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C13 C14 C1 115.72(15) . . ?
C5 C14 C13 121.71(16) . . ?
C5 C14 C1 122.50(15) . . ?
C8 C7 H7 106.5 . . ?
C8 C7 C12 110.43(14) . . ?
C8 C7 C6 114.05(15) . . ?
C12 C7 H7 106.5 . . ?
C6 C7 H7 106.5 . . ?
C6 C7 C12 112.38(14) . . ?
C1 O2 H2 109.5 . . ?
O1 C4 C5 121.24(17) . . ?
O1 C4 C3 122.48(16) . . ?
C5 C4 C3 116.25(16) . . ?
C15 C8 C7 120.19(15) . . ?
C9 C8 C7 119.64(16) . . ?
C9 C8 C15 119.69(17) . . ?
C15 O5 H5 109.5 . . ?
C6 O3 H3 109.5 . . ?
C13 C12 C7 107.49(13) . . ?
C13 C12 C16 108.80(15) . . ?
C7 C12 C16 113.59(14) . . ?
C11 C12 C13 111.22(15) . . ?
C11 C12 C7 109.33(14) . . ?
C11 C12 C16 106.46(14) . . ?
H2A C2 H2B 108.1 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.76(15) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C11 C10 H10 120.2 . . ?
C11 C10 C9 119.62(16) . . ?
C9 C10 H10 120.2 . . ?
O4 C15 C8 122.88(17) . . ?
O4 C15 O5 123.15(17) . . ?
O5 C15 C8 113.94(15) . . ?
C14 C5 C4 121.57(16) . . ?
C14 C5 C6 124.22(15) . . ?
C4 C5 C6 114.07(16) . . ?
C14 C1 H1 107.8 . . ?
O2 C1 C14 112.12(13) . . ?
O2 C1 C2 109.20(14) . . ?
O2 C1 H1 107.8 . . ?
C2 C1 C14 112.05(14) . . ?
C2 C1 H1 107.8 . . ?
C7 C6 H6 108.1 . . ?
O3 C6 C7 109.06(14) . . ?
O3 C6 C5 111.95(15) . . ?
O3 C6 H6 108.1 . . ?
C5 C6 C7 111.42(14) . . ?
C5 C6 H6 108.1 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.73(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C9 C10 121.21(17) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C4 C3 C2 109.56(15) . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
H6A O6 H6B 108.7(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C14 C5 C4 173.48(16) . . . . ?
C13 C14 C5 C6 -1.8(3) . . . . ?
C13 C14 C1 O2 44.4(2) . . . . ?
C13 C14 C1 C2 167.65(15) . . . . ?
C13 C12 C11 C10 155.34(18) . . . . ?
C14 C13 C12 C7 -49.03(19) . . . . ?
C14 C13 C12 C11 -168.67(15) . . . . ?
C14 C13 C12 C16 74.38(18) . . . . ?
C14 C5 C6 C7 13.3(3) . . . . ?
C14 C5 C6 O3 -109.16(19) . . . . ?
C7 C8 C15 O4 -33.7(3) . . . . ?
C7 C8 C15 O5 148.20(16) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C12 C11 C10 36.8(2) . . . . ?
C4 C5 C6 C7 -162.32(14) . . . . ?
C4 C5 C6 O3 75.25(19) . . . . ?
O1 C4 C5 C14 171.24(17) . . . . ?
O1 C4 C5 C6 -13.0(3) . . . . ?
O1 C4 C3 C2 -140.07(18) . . . . ?
C8 C7 C12 C13 -169.22(15) . . . . ?
C8 C7 C12 C11 -48.38(19) . . . . ?
C8 C7 C12 C16 70.36(18) . . . . ?
C8 C7 C6 O3 -46.4(2) . . . . ?
C8 C7 C6 C5 -170.53(15) . . . . ?
C12 C13 C14 C5 20.9(2) . . . . ?
C12 C13 C14 C1 -162.15(15) . . . . ?
C12 C7 C8 C15 -155.05(15) . . . . ?
C12 C7 C8 C9 32.9(2) . . . . ?
C12 C7 C6 O3 80.21(17) . . . . ?
C12 C7 C6 C5 -43.9(2) . . . . ?
C15 C8 C9 C10 -172.20(16) . . . . ?
C5 C14 C1 O2 -138.62(16) . . . . ?
C5 C14 C1 C2 -15.4(2) . . . . ?
C5 C4 C3 C2 42.1(2) . . . . ?
C1 C14 C5 C4 -3.3(3) . . . . ?
C1 C14 C5 C6 -178.56(17) . . . . ?
C1 C2 C3 C4 -60.2(2) . . . . ?
C6 C7 C8 C15 -27.4(2) . . . . ?
C6 C7 C8 C9 160.53(17) . . . . ?
C6 C7 C12 C13 62.19(18) . . . . ?
C6 C7 C12 C11 -176.97(14) . . . . ?
C6 C7 C12 C16 -58.23(19) . . . . ?
C11 C10 C9 C8 -16.0(3) . . . . ?
C16 C12 C11 C10 -86.3(2) . . . . ?
C9 C8 C15 O4 138.34(19) . . . . ?
C9 C8 C15 O5 -39.7(2) . . . . ?
C9 C10 C11 C12 -4.6(3) . . . . ?
C3 C4 C5 C14 -10.9(2) . . . . ?
C3 C4 C5 C6 164.87(16) . . . . ?
C3 C2 C1 C14 46.8(2) . . . . ?
C3 C2 C1 O2 171.65(14) . . . . ?

####################################################################### 
# 
# 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_exp_6178
_database_code_depnum_ccdc_archive 'CCDC 2015767'
loop_
_audit_author_name
_audit_author_address
'archromone D'
;Peking Union Medical College
China
;
_audit_update_record             
;
2020-07-12 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-19
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O5'
_chemical_formula_sum            'C16 H20 O5'
_chemical_formula_weight         292.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.2801(2)
_cell_length_b                   9.9611(3)
_cell_length_c                   18.9298(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1372.75(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2919
_cell_measurement_temperature    111.65(10)
_cell_measurement_theta_max      70.9510
_cell_measurement_theta_min      4.4100
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4464
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.071
_diffrn_reflns_theta_min         5.017
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9726
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -19.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega   28.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega   40.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   46.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega   44.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   97.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega   96.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
  9 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   50.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
 12 omega   67.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   60.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -120.0000 33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1475196000
_diffrn_orient_matrix_UB_12      -0.0153920000
_diffrn_orient_matrix_UB_13      0.0577729000
_diffrn_orient_matrix_UB_21      0.0904412000
_diffrn_orient_matrix_UB_22      -0.1318951000
_diffrn_orient_matrix_UB_23      0.0243967000
_diffrn_orient_matrix_UB_31      0.1218455000
_diffrn_orient_matrix_UB_32      0.0792882000
_diffrn_orient_matrix_UB_33      0.0518492000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2507
_reflns_number_total             2576
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1002 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.3073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.6025(2) -0.97334(16) -0.16129(9) 0.0192(4) Uani 1 1 d . . . . .
H1 H -0.4945 -0.9813 -0.1728 0.029 Uiso 1 1 calc R U . . .
O4 O -1.3877(2) -1.19844(16) -0.36529(8) 0.0161(3) Uani 1 1 d . . . . .
H4 H -1.3532 -1.2754 -0.3575 0.024 Uiso 1 1 calc R U . . .
O5 O -1.1722(2) -0.95257(16) -0.46306(8) 0.0183(4) Uani 1 1 d . . . . .
H5 H -1.1850 -0.9463 -0.5060 0.027 Uiso 1 1 calc R U . . .
O2 O -1.2345(2) -1.05933(19) -0.10331(8) 0.0222(4) Uani 1 1 d . . . . .
O3 O -1.2629(2) -1.00030(16) -0.25394(8) 0.0166(3) Uani 1 1 d . . . . .
C6 C -0.8897(3) -1.1053(2) -0.33265(11) 0.0122(4) Uani 1 1 d . . . . .
C7 C -1.0835(3) -1.1605(2) -0.31575(11) 0.0123(4) Uani 1 1 d . . . . .
H7 H -1.0794 -1.2587 -0.3188 0.015 Uiso 1 1 calc R U . . .
C3 C -1.1655(3) -1.0922(2) -0.44343(11) 0.0146(4) Uani 1 1 d . . . . .
H3 H -1.2507 -1.1412 -0.4741 0.017 Uiso 1 1 calc R U . . .
C9 C -1.0082(3) -1.1017(2) -0.18856(11) 0.0135(4) Uani 1 1 d . . . . .
C10 C -0.8288(3) -1.1241(2) -0.20288(11) 0.0134(4) Uani 1 1 d . . . . .
C8 C -1.1566(3) -1.1220(2) -0.24319(11) 0.0122(4) Uani 1 1 d . . . . .
H8 H -1.2394 -1.1931 -0.2268 0.015 Uiso 1 1 calc R U . . .
C4 C -0.9737(3) -1.1472(2) -0.45648(12) 0.0164(5) Uani 1 1 d . . . . .
H4A H -0.9446 -1.1781 -0.5015 0.020 Uiso 1 1 calc R U . . .
C11 C -0.7633(3) -1.1621(2) -0.27528(11) 0.0146(4) Uani 1 1 d . . . . .
H11A H -0.7594 -1.2592 -0.2792 0.017 Uiso 1 1 calc R U . . .
H11B H -0.6397 -1.1282 -0.2823 0.017 Uiso 1 1 calc R U . . .
C12 C -0.6798(3) -1.1044(2) -0.14792(12) 0.0152(5) Uani 1 1 d . . . . .
H12 H -0.5844 -1.1725 -0.1549 0.018 Uiso 1 1 calc R U . . .
C16 C -0.8724(3) -0.9502(2) -0.33182(12) 0.0152(4) Uani 1 1 d . . . . .
H16A H -0.9145 -0.9163 -0.2872 0.023 Uiso 1 1 calc R U . . .
H16B H -0.9456 -0.9129 -0.3691 0.023 Uiso 1 1 calc R U . . .
H16C H -0.7462 -0.9254 -0.3386 0.023 Uiso 1 1 calc R U . . .
C2 C -1.2320(3) -1.1099(2) -0.36598(11) 0.0124(4) Uani 1 1 d . . . . .
C13 C -0.7517(3) -1.1144(2) -0.07258(12) 0.0185(5) Uani 1 1 d . . . . .
H13A H -0.6579 -1.0835 -0.0401 0.022 Uiso 1 1 calc R U . . .
H13B H -0.7786 -1.2074 -0.0616 0.022 Uiso 1 1 calc R U . . .
C14 C -0.9259(3) -1.0299(2) -0.06275(12) 0.0191(5) Uani 1 1 d . . . . .
H14A H -0.9750 -1.0452 -0.0158 0.023 Uiso 1 1 calc R U . . .
H14B H -0.8948 -0.9355 -0.0667 0.023 Uiso 1 1 calc R U . . .
C1 C -1.2964(3) -0.9815(2) -0.32859(11) 0.0136(4) Uani 1 1 d . . . . .
H1A H -1.2286 -0.9044 -0.3459 0.016 Uiso 1 1 calc R U . . .
H1B H -1.4262 -0.9666 -0.3372 0.016 Uiso 1 1 calc R U . . .
C15 C -1.0702(3) -1.0642(2) -0.11689(12) 0.0160(5) Uani 1 1 d . . . . .
C5 C -0.8461(3) -1.1529(2) -0.40672(12) 0.0158(4) Uani 1 1 d . . . . .
H5A H -0.7299 -1.1862 -0.4172 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C12 1.444(3) . ?
O4 H4 0.8200 . ?
O4 C2 1.436(3) . ?
O5 H5 0.8200 . ?
O5 C3 1.441(3) . ?
O2 C15 1.224(3) . ?
O3 C8 1.453(3) . ?
O3 C1 1.446(2) . ?
C6 C7 1.548(3) . ?
C6 C11 1.532(3) . ?
C6 C16 1.550(3) . ?
C6 C5 1.514(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.522(3) . ?
C7 C2 1.525(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.520(3) . ?
C3 C2 1.554(3) . ?
C9 C10 1.352(3) . ?
C9 C8 1.509(3) . ?
C9 C15 1.478(3) . ?
C10 C11 1.500(3) . ?
C10 C12 1.516(3) . ?
C8 H8 0.9800 . ?
C4 H4A 0.9300 . ?
C4 C5 1.324(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C12 C13 1.522(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 C1 1.535(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.533(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.507(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 H5A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 H1 109.5 . . ?
C2 O4 H4 109.5 . . ?
C3 O5 H5 109.5 . . ?
C1 O3 C8 109.57(15) . . ?
C7 C6 C16 115.24(18) . . ?
C11 C6 C7 105.64(17) . . ?
C11 C6 C16 108.20(17) . . ?
C5 C6 C7 105.73(18) . . ?
C5 C6 C11 114.50(18) . . ?
C5 C6 C16 107.74(18) . . ?
C6 C7 H7 108.3 . . ?
C8 C7 C6 114.56(18) . . ?
C8 C7 H7 108.3 . . ?
C8 C7 C2 103.39(17) . . ?
C2 C7 C6 113.56(17) . . ?
C2 C7 H7 108.3 . . ?
O5 C3 H3 107.8 . . ?
O5 C3 C4 109.70(19) . . ?
O5 C3 C2 109.99(17) . . ?
C4 C3 H3 107.8 . . ?
C4 C3 C2 113.51(18) . . ?
C2 C3 H3 107.8 . . ?
C10 C9 C8 122.1(2) . . ?
C10 C9 C15 121.4(2) . . ?
C15 C9 C8 116.40(19) . . ?
C9 C10 C11 122.1(2) . . ?
C9 C10 C12 122.2(2) . . ?
C11 C10 C12 115.60(19) . . ?
O3 C8 C7 105.66(16) . . ?
O3 C8 C9 111.44(17) . . ?
O3 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 C7 113.70(18) . . ?
C9 C8 H8 108.6 . . ?
C3 C4 H4A 118.5 . . ?
C5 C4 C3 123.0(2) . . ?
C5 C4 H4A 118.5 . . ?
C6 C11 H11A 109.4 . . ?
C6 C11 H11B 109.4 . . ?
C10 C11 C6 111.31(18) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O1 C12 C10 105.97(17) . . ?
O1 C12 H12 109.0 . . ?
O1 C12 C13 110.90(18) . . ?
C10 C12 H12 109.0 . . ?
C10 C12 C13 112.86(19) . . ?
C13 C12 H12 109.0 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C2 C7 110.53(17) . . ?
O4 C2 C3 108.90(17) . . ?
O4 C2 C1 105.45(17) . . ?
C7 C2 C3 113.86(18) . . ?
C7 C2 C1 101.80(16) . . ?
C1 C2 C3 115.85(17) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.26(19) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C13 111.70(18) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
O3 C1 C2 106.92(17) . . ?
O3 C1 H1A 110.3 . . ?
O3 C1 H1B 110.3 . . ?
C2 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
O2 C15 C9 120.1(2) . . ?
O2 C15 C14 122.0(2) . . ?
C9 C15 C14 118.0(2) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5A 120.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C13 C14 71.1(2) . . . . ?
O4 C2 C1 O3 87.96(19) . . . . ?
O5 C3 C4 C5 94.8(3) . . . . ?
O5 C3 C2 O4 120.98(18) . . . . ?
O5 C3 C2 C7 -115.2(2) . . . . ?
O5 C3 C2 C1 2.4(3) . . . . ?
C6 C7 C8 O3 93.1(2) . . . . ?
C6 C7 C8 C9 -29.4(2) . . . . ?
C6 C7 C2 O4 158.62(17) . . . . ?
C6 C7 C2 C3 35.7(3) . . . . ?
C6 C7 C2 C1 -89.7(2) . . . . ?
C7 C6 C11 C10 -57.1(2) . . . . ?
C7 C6 C5 C4 42.8(3) . . . . ?
C7 C2 C1 O3 -27.5(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C3 C2 C1 O3 -151.56(18) . . . . ?
C9 C10 C11 C6 28.7(3) . . . . ?
C9 C10 C12 O1 -98.2(2) . . . . ?
C9 C10 C12 C13 23.4(3) . . . . ?
C10 C9 C8 O3 -123.0(2) . . . . ?
C10 C9 C8 C7 -3.7(3) . . . . ?
C10 C9 C15 O2 -171.7(2) . . . . ?
C10 C9 C15 C14 9.5(3) . . . . ?
C10 C12 C13 C14 -47.6(3) . . . . ?
C8 O3 C1 C2 8.8(2) . . . . ?
C8 C7 C2 O4 -76.6(2) . . . . ?
C8 C7 C2 C3 160.42(17) . . . . ?
C8 C7 C2 C1 35.0(2) . . . . ?
C8 C9 C10 C11 4.0(3) . . . . ?
C8 C9 C10 C12 -179.6(2) . . . . ?
C8 C9 C15 O2 4.5(3) . . . . ?
C8 C9 C15 C14 -174.2(2) . . . . ?
C4 C3 C2 O4 -115.7(2) . . . . ?
C4 C3 C2 C7 8.1(3) . . . . ?
C4 C3 C2 C1 125.7(2) . . . . ?
C11 C6 C7 C8 59.2(2) . . . . ?
C11 C6 C7 C2 177.66(17) . . . . ?
C11 C6 C5 C4 158.7(2) . . . . ?
C11 C10 C12 O1 78.4(2) . . . . ?
C11 C10 C12 C13 -160.05(19) . . . . ?
C12 C10 C11 C6 -147.91(19) . . . . ?
C12 C13 C14 C15 53.4(3) . . . . ?
C16 C6 C7 C8 -60.2(2) . . . . ?
C16 C6 C7 C2 58.3(2) . . . . ?
C16 C6 C11 C10 66.8(2) . . . . ?
C16 C6 C5 C4 -80.9(3) . . . . ?
C2 C7 C8 O3 -31.0(2) . . . . ?
C2 C7 C8 C9 -153.48(18) . . . . ?
C2 C3 C4 C5 -28.7(3) . . . . ?
C13 C14 C15 O2 146.8(2) . . . . ?
C13 C14 C15 C9 -34.5(3) . . . . ?
C1 O3 C8 C7 13.9(2) . . . . ?
C1 O3 C8 C9 137.88(18) . . . . ?
C15 C9 C10 C11 -179.95(19) . . . . ?
C15 C9 C10 C12 -3.6(3) . . . . ?
C15 C9 C8 O3 60.7(2) . . . . ?
C15 C9 C8 C7 -179.99(18) . . . . ?
C5 C6 C7 C8 -179.07(18) . . . . ?
C5 C6 C7 C2 -60.6(2) . . . . ?
C5 C6 C11 C10 -173.04(19) . . . . ?

_shelx_estimated_absorpt_T_max   0.781
_shelx_estimated_absorpt_T_min   0.751
_shelx_SHELXL_version_number     2014/7
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
####################################################################### 
# 
# 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_exp_6087
_database_code_depnum_ccdc_archive 'CCDC 2015768'
loop_
_audit_author_name
_audit_author_address
'archromone E'
;Peking Union Medical College
China
;
_audit_update_record             
;
2020-07-12 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_audit_creation_date             2019-06-04
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O5'
_chemical_formula_sum            'C16 H20 O5'
_chemical_formula_weight         292.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   16.8403(3)
_cell_length_b                   10.54278(19)
_cell_length_c                   7.78736(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1382.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4898
_cell_measurement_temperature    110.20(14)
_cell_measurement_theta_max      71.0330
_cell_measurement_theta_min      4.9370
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9189
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.163
_diffrn_reflns_theta_min         4.949
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.20(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9904
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega   61.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega   46.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036    0.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   97.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega   53.00  107.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   56.00  115.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega   48.00   91.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
  8 omega   47.00   84.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   92.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega   46.00   91.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   54.00  107.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   53.00   80.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   65.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   41.00   87.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega   93.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 16 omega  139.00  173.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega    8.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  -34.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036    0.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 20 omega  -34.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -37.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
 21 omega   22.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -77.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 22 omega   -1.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -99.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
 23 omega   66.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -178.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 24 omega   51.00  107.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 25 omega   38.00   89.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 26 omega   50.00  175.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  120.0000 125

#__ type_ start__ end____ width___ exp.time_
 27 omega   20.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   57.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 28 omega  -33.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -77.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
 29 omega  -17.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -57.0000  120.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0153303000
_diffrn_orient_matrix_UB_12      0.0429133000
_diffrn_orient_matrix_UB_13      0.1862563000
_diffrn_orient_matrix_UB_21      0.0757432000
_diffrn_orient_matrix_UB_22      -0.0696674000
_diffrn_orient_matrix_UB_23      0.0584871000
_diffrn_orient_matrix_UB_31      0.0489577000
_diffrn_orient_matrix_UB_32      0.1210510000
_diffrn_orient_matrix_UB_33      -0.0321035000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2576
_reflns_number_total             2657
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1044 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.3251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0895
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21340(9) 1.00116(15) 0.36510(19) 0.0174(3) Uani 1 1 d . . . . .
O4 O 0.37584(9) 1.00409(16) 0.2076(2) 0.0227(4) Uani 1 1 d . . . . .
O5 O 0.26203(10) 0.69799(15) -0.15603(19) 0.0207(4) Uani 1 1 d . . . . .
H5 H 0.2595 0.6372 -0.2215 0.031 Uiso 1 1 calc R U . . .
O3 O 0.09307(10) 0.53758(15) 0.4499(2) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.1051 0.5452 0.5514 0.032 Uiso 1 1 calc R U . . .
O2 O 0.17553(10) 0.90239(14) 0.7286(2) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.1935 0.8349 0.7636 0.028 Uiso 1 1 calc R U . . .
C10 C 0.26269(12) 0.7220(2) 0.1452(3) 0.0146(4) Uani 1 1 d . . . . .
C11 C 0.18973(12) 0.6515(2) 0.2007(3) 0.0162(4) Uani 1 1 d . . . . .
H11A H 0.2053 0.5793 0.2701 0.019 Uiso 1 1 calc R U . . .
H11B H 0.1624 0.6195 0.0999 0.019 Uiso 1 1 calc R U . . .
C9 C 0.28788(12) 0.8298(2) 0.2206(3) 0.0147(4) Uani 1 1 d . . . . .
C4 C 0.02283(12) 0.7317(2) 0.5219(3) 0.0198(5) Uani 1 1 d . . . . .
H4 H -0.0278 0.7056 0.5542 0.024 Uiso 1 1 calc R U . . .
C12 C 0.35516(13) 0.9023(2) 0.1475(3) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.05328(13) 0.8335(2) 0.5986(3) 0.0190(5) Uani 1 1 d . . . . .
H3A H 0.0215 0.8772 0.6763 0.023 Uiso 1 1 calc R U . . .
C14 C 0.39129(13) 0.7055(2) -0.0178(3) 0.0231(5) Uani 1 1 d . . . . .
H14A H 0.4140 0.6761 -0.1252 0.028 Uiso 1 1 calc R U . . .
H14B H 0.4216 0.6687 0.0756 0.028 Uiso 1 1 calc R U . . .
C8 C 0.25003(12) 0.87679(19) 0.3856(3) 0.0141(4) Uani 1 1 d . . . . .
H8 H 0.2910 0.8823 0.4746 0.017 Uiso 1 1 calc R U . . .
C2 C 0.13631(12) 0.8824(2) 0.5672(3) 0.0154(4) Uani 1 1 d . . . . .
C15 C 0.30564(12) 0.6627(2) -0.0054(3) 0.0172(4) Uani 1 1 d . . . . .
H15 H 0.3043 0.5702 0.0067 0.021 Uiso 1 1 calc R U . . .
C7 C 0.18313(11) 0.79265(19) 0.4501(3) 0.0129(4) Uani 1 1 d . . . . .
H7 H 0.2056 0.7239 0.5196 0.015 Uiso 1 1 calc R U . . .
C1 C 0.14355(12) 1.0102(2) 0.4736(3) 0.0166(4) Uani 1 1 d . . . . .
H1A H 0.0966 1.0261 0.4046 0.020 Uiso 1 1 calc R U . . .
H1B H 0.1494 1.0788 0.5556 0.020 Uiso 1 1 calc R U . . .
C16 C 0.09411(13) 0.8305(2) 0.1794(3) 0.0180(4) Uani 1 1 d . . . . .
H16A H 0.1336 0.8887 0.1384 0.027 Uiso 1 1 calc R U . . .
H16B H 0.0532 0.8766 0.2385 0.027 Uiso 1 1 calc R U . . .
H16C H 0.0714 0.7857 0.0840 0.027 Uiso 1 1 calc R U . . .
C13 C 0.39659(13) 0.8497(2) -0.0091(3) 0.0245(5) Uani 1 1 d . . . . .
H13A H 0.4520 0.8747 -0.0067 0.029 Uiso 1 1 calc R U . . .
H13B H 0.3728 0.8857 -0.1115 0.029 Uiso 1 1 calc R U . . .
C6 C 0.13286(11) 0.73490(19) 0.3038(3) 0.0141(4) Uani 1 1 d . . . . .
C5 C 0.06543(13) 0.6559(2) 0.3856(3) 0.0174(4) Uani 1 1 d . . . . .
H5A H 0.0268 0.6375 0.2949 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.458(2) . ?
O1 C1 1.451(2) . ?
O4 C12 1.222(3) . ?
O5 H5 0.8200 . ?
O5 C15 1.433(3) . ?
O3 H3 0.8200 . ?
O3 C5 1.423(3) . ?
O2 H2 0.8200 . ?
O2 C2 1.436(3) . ?
C10 C11 1.500(3) . ?
C10 C9 1.347(3) . ?
C10 C15 1.513(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C6 1.528(3) . ?
C9 C12 1.480(3) . ?
C9 C8 1.517(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.332(3) . ?
C4 C5 1.509(3) . ?
C12 C13 1.510(3) . ?
C3 H3A 0.9300 . ?
C3 C2 1.510(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.514(3) . ?
C14 C13 1.524(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.520(3) . ?
C2 C7 1.532(3) . ?
C2 C1 1.536(3) . ?
C15 H15 0.9800 . ?
C7 H7 0.9800 . ?
C7 C6 1.545(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C6 1.543(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C6 C5 1.546(3) . ?
C5 H5A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C8 109.77(16) . . ?
C15 O5 H5 109.5 . . ?
C5 O3 H3 109.5 . . ?
C2 O2 H2 109.5 . . ?
C11 C10 C15 114.21(18) . . ?
C9 C10 C11 123.40(19) . . ?
C9 C10 C15 122.38(19) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C6 112.32(17) . . ?
H11A C11 H11B 107.9 . . ?
C6 C11 H11A 109.1 . . ?
C6 C11 H11B 109.1 . . ?
C10 C9 C12 120.57(19) . . ?
C10 C9 C8 120.80(19) . . ?
C12 C9 C8 118.59(18) . . ?
C3 C4 H4 118.0 . . ?
C3 C4 C5 123.99(19) . . ?
C5 C4 H4 118.0 . . ?
O4 C12 C9 121.6(2) . . ?
O4 C12 C13 120.0(2) . . ?
C9 C12 C13 118.33(19) . . ?
C4 C3 H3A 118.0 . . ?
C4 C3 C2 124.0(2) . . ?
C2 C3 H3A 118.0 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C15 C14 C13 110.49(18) . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
O1 C8 C9 112.26(17) . . ?
O1 C8 H8 108.8 . . ?
O1 C8 C7 104.34(16) . . ?
C9 C8 H8 108.8 . . ?
C9 C8 C7 113.64(17) . . ?
C7 C8 H8 108.8 . . ?
O2 C2 C3 109.51(17) . . ?
O2 C2 C7 112.00(17) . . ?
O2 C2 C1 104.51(17) . . ?
C3 C2 C7 111.21(18) . . ?
C3 C2 C1 116.73(17) . . ?
C7 C2 C1 102.63(17) . . ?
O5 C15 C10 106.40(16) . . ?
O5 C15 C14 111.02(18) . . ?
O5 C15 H15 109.0 . . ?
C10 C15 C14 112.44(18) . . ?
C10 C15 H15 109.0 . . ?
C14 C15 H15 109.0 . . ?
C8 C7 C2 102.56(16) . . ?
C8 C7 H7 109.1 . . ?
C8 C7 C6 113.10(16) . . ?
C2 C7 H7 109.1 . . ?
C2 C7 C6 113.59(16) . . ?
C6 C7 H7 109.1 . . ?
O1 C1 C2 106.44(16) . . ?
O1 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
C12 C13 C14 112.0(2) . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C11 C6 C7 105.72(16) . . ?
C11 C6 C16 108.13(17) . . ?
C11 C6 C5 111.56(17) . . ?
C7 C6 C5 108.09(16) . . ?
C16 C6 C7 115.94(17) . . ?
C16 C6 C5 107.46(16) . . ?
O3 C5 C4 111.86(18) . . ?
O3 C5 C6 112.15(17) . . ?
O3 C5 H5A 107.3 . . ?
C4 C5 C6 110.75(18) . . ?
C4 C5 H5A 107.3 . . ?
C6 C5 H5A 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C7 C2 -36.30(19) . . . . ?
O1 C8 C7 C6 86.44(19) . . . . ?
O4 C12 C13 C14 154.2(2) . . . . ?
O2 C2 C7 C8 -76.0(2) . . . . ?
O2 C2 C7 C6 161.56(16) . . . . ?
O2 C2 C1 O1 94.67(19) . . . . ?
C10 C11 C6 C7 -53.1(2) . . . . ?
C10 C11 C6 C16 71.7(2) . . . . ?
C10 C11 C6 C5 -170.35(17) . . . . ?
C10 C9 C12 O4 175.5(2) . . . . ?
C10 C9 C12 C13 -2.3(3) . . . . ?
C10 C9 C8 O1 -118.8(2) . . . . ?
C10 C9 C8 C7 -0.7(3) . . . . ?
C11 C10 C9 C12 -173.16(19) . . . . ?
C11 C10 C9 C8 9.1(3) . . . . ?
C11 C10 C15 O5 78.7(2) . . . . ?
C11 C10 C15 C14 -159.57(18) . . . . ?
C11 C6 C5 O3 39.6(2) . . . . ?
C11 C6 C5 C4 165.38(17) . . . . ?
C9 C10 C11 C6 20.0(3) . . . . ?
C9 C10 C15 O5 -100.5(2) . . . . ?
C9 C10 C15 C14 21.2(3) . . . . ?
C9 C12 C13 C14 -28.0(3) . . . . ?
C9 C8 C7 C2 -158.89(16) . . . . ?
C9 C8 C7 C6 -36.1(2) . . . . ?
C4 C3 C2 O2 -129.9(2) . . . . ?
C4 C3 C2 C7 -5.6(3) . . . . ?
C4 C3 C2 C1 111.6(2) . . . . ?
C12 C9 C8 O1 63.4(2) . . . . ?
C12 C9 C8 C7 -178.48(18) . . . . ?
C3 C4 C5 O3 106.2(2) . . . . ?
C3 C4 C5 C6 -19.7(3) . . . . ?
C3 C2 C7 C8 161.07(17) . . . . ?
C3 C2 C7 C6 38.7(2) . . . . ?
C3 C2 C1 O1 -144.23(18) . . . . ?
C8 O1 C1 C2 -0.2(2) . . . . ?
C8 C9 C12 O4 -6.8(3) . . . . ?
C8 C9 C12 C13 175.42(19) . . . . ?
C8 C7 C6 C11 62.5(2) . . . . ?
C8 C7 C6 C16 -57.3(2) . . . . ?
C8 C7 C6 C5 -177.94(16) . . . . ?
C2 C7 C6 C11 178.87(17) . . . . ?
C2 C7 C6 C16 59.1(2) . . . . ?
C2 C7 C6 C5 -61.6(2) . . . . ?
C15 C10 C11 C6 -159.22(17) . . . . ?
C15 C10 C9 C12 6.0(3) . . . . ?
C15 C10 C9 C8 -171.71(18) . . . . ?
C15 C14 C13 C12 53.7(3) . . . . ?
C7 C2 C1 O1 -22.4(2) . . . . ?
C7 C6 C5 O3 -76.2(2) . . . . ?
C7 C6 C5 C4 49.6(2) . . . . ?
C1 O1 C8 C9 146.54(17) . . . . ?
C1 O1 C8 C7 23.1(2) . . . . ?
C1 C2 C7 C8 35.52(19) . . . . ?
C1 C2 C7 C6 -86.9(2) . . . . ?
C16 C6 C5 O3 158.00(17) . . . . ?
C16 C6 C5 C4 -76.3(2) . . . . ?
C13 C14 C15 O5 68.7(2) . . . . ?
C13 C14 C15 C10 -50.4(3) . . . . ?
C5 C4 C3 C2 -3.7(3) . . . . ?

_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.742
_shelx_SHELXL_version_number     2014/7
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
####################################################################### 
# 
# 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_yhw_43a
_database_code_depnum_ccdc_archive 'CCDC 2015765'
loop_
_audit_author_name
_audit_author_address
'archromone C'
;Peking Union Medical College
China
;
_audit_update_record             
;
2020-07-12 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.16170(10)
_cell_length_b                   9.7401(2)
_cell_length_c                   18.6984(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1304.32(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10120
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      74.7620
_cell_measurement_theta_min      4.7460
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.840
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12549
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.233
_diffrn_reflns_theta_min         4.730
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -38.00   0.50    0.05    --  -47.70 -36.00-166.00  166
  2  ω   -128.00 -89.00   0.50    0.07    -- -101.00 -86.00  23.00   78
  3  ω   -173.00-141.00   0.50    0.07    -- -101.00 -86.00  23.00   64
  4  ω     31.00  88.00   0.50    0.07    --  103.25-144.00 -32.00  114
  5  ω   -119.00 -93.00   0.50    0.05    --  -47.70-125.00 -30.00   52
  6  ω   -111.00 -85.00   0.50    0.05    --  -47.70-125.00  90.00   52
  7  ω     25.00  91.00   0.50    0.05    --   47.70-125.00-120.00  132
  8  ω    -73.00 -36.00   0.50    0.07    -- -101.00 125.00 150.00   74
  9  ω   -110.00 -77.00   0.50    0.07    -- -101.00 125.00 150.00   66
 10  ω   -104.00 -79.00   0.50    0.07    -- -101.00  30.00-180.00   50
 11  ω   -120.00 -35.00   0.50    0.07    -- -101.00  77.00  30.00  170
 12  ω    -72.00 -29.00   0.50    0.07    -- -101.00  30.00-180.00   86
 13  ω   -169.00 -91.00   0.50    0.07    -- -101.00-125.00  90.00  156
 14  ω     49.00 103.00   0.50    0.07    --  103.25-126.00 136.00  108
 15  ω    100.00 125.00   0.50    0.07    --  103.25-144.00 -32.00   50
 16  ω   -103.00 -76.00   0.50    0.05    --  -47.70-125.00  60.00   54
 17  ω     34.00  60.00   0.50    0.07    --  103.25-125.00  30.00   52
 18  ω    -71.00 -46.00   0.50    0.07    -- -101.00  36.00 -10.00   50
 19  ω    107.00 132.00   0.50    0.07    --  103.25  86.00 141.00   50
 20  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -30.00  188
 21  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00  60.00  188
 22  ω   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00 120.00  172
 23  ω    -24.00  74.00   0.50    0.05    --   47.70 -86.00  23.00  196
 24  ω   -174.00-123.00   0.50    0.07    -- -101.00 -30.00 120.00  102
 25  ω     90.00 178.00   0.50    0.07    --  103.25  15.00-120.00  176
 26  ω      1.00  26.00   0.50    0.05    --   47.70 -86.00  23.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0257726000
_diffrn_orient_matrix_UB_12      0.0018801000
_diffrn_orient_matrix_UB_13      0.0818066000
_diffrn_orient_matrix_UB_21      -0.1900882000
_diffrn_orient_matrix_UB_22      -0.0723810000
_diffrn_orient_matrix_UB_23      -0.0083117000
_diffrn_orient_matrix_UB_31      0.0973579000
_diffrn_orient_matrix_UB_32      -0.1405845000
_diffrn_orient_matrix_UB_33      0.0053884000
_diffrn_oxdiff_digest_frames     
;
01d99e55b864864eb2f949961240742c540269626e3
;
_diffrn_oxdiff_digest_hkl        
;
01062fb321597750d869354b3f545fc60c2893
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                2473
_reflns_number_total             2589
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2589
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.3062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1397(2) 0.45644(17) 0.58029(8) 0.0308(4) Uani 1 1 d . . . . .
H1 H 0.0403 0.4483 0.6016 0.046 Uiso 1 1 calc GR . . . .
O2 O 0.7917(2) 0.41124(17) 0.64473(8) 0.0317(4) Uani 1 1 d . . . . .
O3 O 0.6209(2) 0.46726(15) 0.79089(8) 0.0291(3) Uani 1 1 d . . . . .
C1 C 0.2456(3) 0.3329(2) 0.58756(10) 0.0231(4) Uani 1 1 d . . . . .
H1A H 0.1650 0.2544 0.5767 0.028 Uiso 1 1 calc R . . . .
C2 C 0.4031(3) 0.3381(2) 0.53324(10) 0.0268(5) Uani 1 1 d . . . . .
H2A H 0.3538 0.3652 0.4870 0.032 Uiso 1 1 calc R . . . .
H2B H 0.4580 0.2475 0.5283 0.032 Uiso 1 1 calc R . . . .
C3 C 0.5530(3) 0.4401(2) 0.55659(11) 0.0263(5) Uani 1 1 d . . . . .
H3A H 0.6550 0.4390 0.5225 0.032 Uiso 1 1 calc R . . . .
H3B H 0.5008 0.5320 0.5574 0.032 Uiso 1 1 calc R . . . .
C4 C 0.6256(3) 0.4040(2) 0.62961(10) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.4884(2) 0.3584(2) 0.68354(10) 0.0184(4) Uani 1 1 d . . . . .
C6 C 0.5576(3) 0.3397(2) 0.75914(10) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.6621 0.2747 0.7586 0.025 Uiso 1 1 calc R . . . .
C7 C 0.4098(3) 0.2866(2) 0.80989(10) 0.0194(4) Uani 1 1 d . . . . .
H7 H 0.4219 0.1867 0.8144 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4562(3) 0.3532(2) 0.88035(11) 0.0256(4) Uani 1 1 d . . . . .
C9 C 0.3323(3) 0.3430(2) 0.93354(10) 0.0291(5) Uani 1 1 d . . . . .
H9 H 0.3562 0.3806 0.9783 0.035 Uiso 1 1 calc R . . . .
C10 C 0.1569(3) 0.2701(3) 0.91859(11) 0.0316(5) Uani 1 1 d . . . . .
H10 H 0.0891 0.2316 0.9559 0.038 Uiso 1 1 calc R . . . .
C11 C 0.0947(3) 0.2590(2) 0.85150(11) 0.0276(5) Uani 1 1 d . . . . .
H11 H -0.0162 0.2130 0.8418 0.033 Uiso 1 1 calc R . . . .
C12 C 0.2080(3) 0.3227(2) 0.79107(10) 0.0204(4) Uani 1 1 d . . . . .
C13 C 0.1728(3) 0.2653(2) 0.71644(10) 0.0203(4) Uani 1 1 d . . . . .
H13A H 0.1807 0.1659 0.7177 0.024 Uiso 1 1 calc R . . . .
H13B H 0.0481 0.2902 0.7009 0.024 Uiso 1 1 calc R . . . .
C14 C 0.3141(3) 0.32064(19) 0.66402(10) 0.0184(4) Uani 1 1 d . . . . .
C15 C 0.6227(3) 0.4433(2) 0.86709(11) 0.0317(5) Uani 1 1 d . . . . .
H15A H 0.6117 0.5290 0.8932 0.038 Uiso 1 1 calc R . . . .
H15B H 0.7370 0.3975 0.8815 0.038 Uiso 1 1 calc R . . . .
C16 C 0.1633(3) 0.4779(2) 0.78941(11) 0.0260(4) Uani 1 1 d . . . . .
H16A H 0.1894 0.5174 0.8354 0.039 Uiso 1 1 calc GR . . . .
H16B H 0.0338 0.4909 0.7781 0.039 Uiso 1 1 calc GR . . . .
H16C H 0.2390 0.5219 0.7538 0.039 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.429(3) . ?
O2 C4 1.225(3) . ?
O3 C6 1.450(2) . ?
O3 C15 1.444(3) . ?
C1 H1A 0.9800 . ?
C1 C2 1.519(3) . ?
C1 C14 1.516(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.526(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.503(3) . ?
C4 C5 1.476(3) . ?
C5 C6 1.509(3) . ?
C5 C14 1.352(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.513(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.505(3) . ?
C7 C12 1.529(3) . ?
C8 C9 1.336(3) . ?
C8 C15 1.501(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.470(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.335(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.523(3) . ?
C12 C13 1.525(3) . ?
C12 C16 1.545(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.508(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C15 O3 C6 105.55(15) . . ?
O1 C1 H1A 109.0 . . ?
O1 C1 C2 107.62(16) . . ?
O1 C1 C14 109.14(16) . . ?
C2 C1 H1A 109.0 . . ?
C14 C1 H1A 109.0 . . ?
C14 C1 C2 113.15(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.63(16) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.57(17) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
O2 C4 C3 122.19(18) . . ?
O2 C4 C5 120.39(18) . . ?
C5 C4 C3 117.42(17) . . ?
C4 C5 C6 117.24(16) . . ?
C14 C5 C4 120.81(17) . . ?
C14 C5 C6 121.56(17) . . ?
O3 C6 C5 112.51(16) . . ?
O3 C6 H6 108.6 . . ?
O3 C6 C7 104.78(15) . . ?
C5 C6 H6 108.6 . . ?
C5 C6 C7 113.53(15) . . ?
C7 C6 H6 108.6 . . ?
C6 C7 H7 109.4 . . ?
C6 C7 C12 115.98(16) . . ?
C8 C7 C6 104.32(16) . . ?
C8 C7 H7 109.4 . . ?
C8 C7 C12 108.09(16) . . ?
C12 C7 H7 109.4 . . ?
C9 C8 C7 118.24(19) . . ?
C9 C8 C15 133.9(2) . . ?
C15 C8 C7 106.41(17) . . ?
C8 C9 H9 121.3 . . ?
C8 C9 C10 117.48(19) . . ?
C10 C9 H9 121.3 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.19(19) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.1(2) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C16 115.21(16) . . ?
C11 C12 C7 103.81(15) . . ?
C11 C12 C13 116.19(16) . . ?
C11 C12 C16 107.65(16) . . ?
C13 C12 C7 106.40(15) . . ?
C13 C12 C16 107.85(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 C12 110.65(15) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C5 C14 C1 122.13(17) . . ?
C5 C14 C13 122.78(17) . . ?
C13 C14 C1 115.08(15) . . ?
O3 C15 C8 104.52(16) . . ?
O3 C15 H15A 110.8 . . ?
O3 C15 H15B 110.8 . . ?
C8 C15 H15A 110.8 . . ?
C8 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.99 2.803(2) 173.1 1_455

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 73.4(2) . . . . ?
O1 C1 C14 C5 -98.1(2) . . . . ?
O1 C1 C14 C13 81.11(19) . . . . ?
O2 C4 C5 C6 7.8(3) . . . . ?
O2 C4 C5 C14 -165.1(2) . . . . ?
O3 C6 C7 C8 -23.42(19) . . . . ?
O3 C6 C7 C12 95.32(18) . . . . ?
C1 C2 C3 C4 56.6(2) . . . . ?
C2 C1 C14 C5 21.7(3) . . . . ?
C2 C1 C14 C13 -159.10(18) . . . . ?
C2 C3 C4 O2 139.1(2) . . . . ?
C2 C3 C4 C5 -40.7(2) . . . . ?
C3 C4 C5 C6 -172.40(18) . . . . ?
C3 C4 C5 C14 14.8(3) . . . . ?
C4 C5 C6 O3 63.9(2) . . . . ?
C4 C5 C6 C7 -177.31(17) . . . . ?
C4 C5 C14 C1 -4.7(3) . . . . ?
C4 C5 C14 C13 176.21(17) . . . . ?
C5 C6 C7 C8 -146.56(17) . . . . ?
C5 C6 C7 C12 -27.8(2) . . . . ?
C6 O3 C15 C8 -36.6(2) . . . . ?
C6 C5 C14 C1 -177.20(18) . . . . ?
C6 C5 C14 C13 3.7(3) . . . . ?
C6 C7 C8 C9 169.60(19) . . . . ?
C6 C7 C8 C15 1.4(2) . . . . ?
C6 C7 C12 C11 -178.87(16) . . . . ?
C6 C7 C12 C13 58.0(2) . . . . ?
C6 C7 C12 C16 -61.4(2) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C7 C8 C15 O3 21.1(2) . . . . ?
C7 C12 C13 C14 -56.0(2) . . . . ?
C8 C7 C12 C11 -62.2(2) . . . . ?
C8 C7 C12 C13 174.68(16) . . . . ?
C8 C7 C12 C16 55.2(2) . . . . ?
C8 C9 C10 C11 -23.4(3) . . . . ?
C9 C8 C15 O3 -144.4(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C7 42.2(3) . . . . ?
C10 C11 C12 C13 158.6(2) . . . . ?
C10 C11 C12 C16 -80.4(2) . . . . ?
C11 C12 C13 C14 -170.99(16) . . . . ?
C12 C7 C8 C9 45.6(2) . . . . ?
C12 C7 C8 C15 -122.54(18) . . . . ?
C12 C13 C14 C1 -150.56(16) . . . . ?
C12 C13 C14 C5 28.6(3) . . . . ?
C14 C1 C2 C3 -47.2(2) . . . . ?
C14 C5 C6 O3 -123.32(19) . . . . ?
C14 C5 C6 C7 -4.5(3) . . . . ?
C15 O3 C6 C5 161.53(16) . . . . ?
C15 O3 C6 C7 37.73(19) . . . . ?
C15 C8 C9 C10 162.6(2) . . . . ?
C16 C12 C13 C14 68.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.860
_oxdiff_exptl_absorpt_empirical_full_min 0.371
