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

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

data_exp_5894
_database_code_depnum_ccdc_archive 'CCDC 1922181'
loop_
_audit_author_name
_audit_author_address
'Zhaocui Sun'
;Peking Union Medical College and Chinese Academy of Medical Sciences
China
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;
_audit_creation_date             2019-04-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 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                   10.0737(5)
_cell_length_b                   6.13340(19)
_cell_length_c                   13.8766(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.776(5)
_cell_angle_gamma                90
_cell_volume                     816.45(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3624
_cell_measurement_temperature    109.2(5)
_cell_measurement_theta_max      71.0160
_cell_measurement_theta_min      4.5660
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92162
_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    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5154
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.147
_diffrn_reflns_theta_min         4.610
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.2(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9721
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega   78.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   94.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega  103.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega   96.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  140.0000  -77.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   26.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  8 omega   49.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   52.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega   63.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega   78.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 14 omega   47.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -129.0000   36.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega   47.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 16 omega   59.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
 17 omega   47.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 18 omega   88.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 19 omega   68.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 20 omega   20.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 21 omega   10.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
 22 omega   45.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
 23 omega   45.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 24 omega   48.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 25 omega   40.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   10.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega  -27.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 28 omega  -32.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -120.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1131350000
_diffrn_orient_matrix_UB_12      -0.0727938000
_diffrn_orient_matrix_UB_13      -0.0970105000
_diffrn_orient_matrix_UB_21      0.0301305000
_diffrn_orient_matrix_UB_22      -0.2402079000
_diffrn_orient_matrix_UB_23      0.0315599000
_diffrn_orient_matrix_UB_31      -0.1098857000
_diffrn_orient_matrix_UB_32      0.0092073000
_diffrn_orient_matrix_UB_33      0.0565037000
_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         0.792
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3030
_reflns_number_total             3091
_reflns_odcompleteness_completeness 99.88
_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         0.209
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.047
_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)+(0.0635P)²+0.1327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0945
_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 -0.42726(18) -0.2658(3) -0.63268(13) 0.0214(4) Uani 1 1 d . . . . .
O4 O -0.14903(19) -1.0575(3) -0.85558(13) 0.0216(4) Uani 1 1 d . . . . .
O2 O -0.54142(16) -0.5881(3) -0.77595(12) 0.0183(4) Uani 1 1 d . . . . .
O5 O -0.42352(17) -0.3218(3) -0.97566(12) 0.0207(4) Uani 1 1 d . . . . .
O3 O -0.62257(18) -0.7149(3) -0.65329(13) 0.0250(4) Uani 1 1 d . . . . .
C1 C -0.2056(2) -0.8819(4) -0.88453(16) 0.0152(4) Uani 1 1 d . . . . .
C6 C -0.4243(2) -0.4570(4) -0.78577(17) 0.0168(5) Uani 1 1 d . . . . .
H6 H -0.4615 -0.3232 -0.8228 0.020 Uiso 1 1 calc R U . . .
C14 C -0.2712(2) -0.7647(4) -0.81412(16) 0.0144(4) Uani 1 1 d . . . . .
N1 N -0.2877(2) -0.4775(4) -1.09375(15) 0.0190(4) Uani 1 1 d . . . . .
H1 H -0.3576 -0.3910 -1.1155 0.023 Uiso 1 1 calc R U . . .
C2 C -0.2114(2) -0.7892(4) -0.98272(17) 0.0143(4) Uani 1 1 d . . . . .
C17 C -0.1504(2) -0.9260(4) -1.04466(18) 0.0174(5) Uani 1 1 d . . . . .
H17 H -0.1112 -1.0556 -1.0142 0.021 Uiso 1 1 calc R U . . .
C3 C -0.2781(2) -0.5926(4) -1.01004(16) 0.0152(5) Uani 1 1 d . . . . .
C9 C -0.3465(2) -0.5735(4) -0.50264(17) 0.0188(5) Uani 1 1 d . . . . .
H9A H -0.4187 -0.5921 -0.4705 0.023 Uiso 1 1 calc R U . . .
H9B H -0.2820 -0.4636 -0.4652 0.023 Uiso 1 1 calc R U . . .
C7 C -0.3436(2) -0.3971(4) -0.67805(17) 0.0165(5) Uani 1 1 d . . . . .
H7 H -0.2421 -0.3789 -0.6579 0.020 Uiso 1 1 calc R U . . .
C4 C -0.3555(2) -0.4868(4) -0.94545(16) 0.0150(5) Uani 1 1 d . . . . .
C11 C -0.1408(2) -0.7604(4) -0.53344(18) 0.0194(5) Uani 1 1 d . . . . .
H11 H -0.0596 -0.7181 -0.4840 0.023 Uiso 1 1 calc R U . . .
C5 C -0.3454(2) -0.5814(4) -0.84465(17) 0.0145(4) Uani 1 1 d . . . . .
C13 C -0.2512(2) -0.8759(4) -0.71360(17) 0.0157(4) Uani 1 1 d . . . . .
H13A H -0.2356 -1.0301 -0.7214 0.019 Uiso 1 1 calc R U . . .
H13B H -0.3368 -0.8621 -0.6958 0.019 Uiso 1 1 calc R U . . .
C16 C -0.5368(2) -0.6131(4) -0.67740(18) 0.0174(5) Uani 1 1 d . . . . .
C18 C -0.1420(3) -0.8944(4) -1.13863(18) 0.0203(5) Uani 1 1 d . . . . .
H18 H -0.1007 -1.0064 -1.1645 0.024 Uiso 1 1 calc R U . . .
C20 C -0.1879(2) -0.4884(4) -1.15090(17) 0.0190(5) Uani 1 1 d . . . . .
H20A H -0.0949 -0.4656 -1.1048 0.023 Uiso 1 1 calc R U . . .
H20B H -0.2073 -0.3706 -1.1999 0.023 Uiso 1 1 calc R U . . .
C12 C -0.1314(2) -0.7879(4) -0.62645(17) 0.0177(5) Uani 1 1 d . . . . .
C10 C -0.2686(3) -0.7902(4) -0.49932(17) 0.0204(5) Uani 1 1 d . . . . .
H10A H -0.2408 -0.8470 -0.4308 0.025 Uiso 1 1 calc R U . . .
H10B H -0.3304 -0.8955 -0.5429 0.025 Uiso 1 1 calc R U . . .
C15 C 0.0018(2) -0.7394(5) -0.65039(19) 0.0245(5) Uani 1 1 d . . . . .
H15A H -0.0150 -0.6276 -0.7011 0.037 Uiso 1 1 calc R U . . .
H15B H 0.0337 -0.8691 -0.6751 0.037 Uiso 1 1 calc R U . . .
H15C H 0.0715 -0.6906 -0.5902 0.037 Uiso 1 1 calc R U . . .
C19 C -0.1902(3) -0.7032(5) -1.20645(17) 0.0213(5) Uani 1 1 d . . . . .
H19A H -0.2846 -0.7306 -1.2493 0.026 Uiso 1 1 calc R U . . .
H19B H -0.1315 -0.6892 -1.2500 0.026 Uiso 1 1 calc R U . . .
C8 C -0.4106(2) -0.4984(4) -0.60907(18) 0.0170(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.442(3) . ?
O1 C8 1.462(3) . ?
O4 C1 1.227(3) . ?
O2 C6 1.468(3) . ?
O2 C16 1.363(3) . ?
O5 C4 1.222(3) . ?
O3 C16 1.194(3) . ?
C1 C14 1.517(3) . ?
C1 C2 1.461(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.513(3) . ?
C6 C5 1.510(3) . ?
C14 C5 1.345(3) . ?
C14 C13 1.510(3) . ?
N1 H1 0.8600 . ?
N1 C3 1.337(3) . ?
N1 C20 1.460(3) . ?
C2 C17 1.464(3) . ?
C2 C3 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.346(3) . ?
C3 C4 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.537(3) . ?
C9 C8 1.493(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.468(3) . ?
C4 C5 1.489(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.333(3) . ?
C11 C10 1.512(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.523(3) . ?
C16 C8 1.508(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.489(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.523(4) . ?
C12 C15 1.507(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C7 O1 C8 60.71(14) . . ?
C16 O2 C6 111.87(18) . . ?
O4 C1 C14 117.1(2) . . ?
O4 C1 C2 122.0(2) . . ?
C2 C1 C14 121.0(2) . . ?
O2 C6 H6 108.6 . . ?
O2 C6 C7 104.27(17) . . ?
O2 C6 C5 110.14(19) . . ?
C7 C6 H6 108.6 . . ?
C5 C6 H6 108.6 . . ?
C5 C6 C7 116.36(19) . . ?
C5 C14 C1 120.2(2) . . ?
C5 C14 C13 124.9(2) . . ?
C13 C14 C1 114.82(19) . . ?
C3 N1 H1 117.7 . . ?
C3 N1 C20 124.7(2) . . ?
C20 N1 H1 117.7 . . ?
C1 C2 C17 114.8(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C17 126.7(2) . . ?
C2 C17 H17 114.8 . . ?
C18 C17 C2 130.4(2) . . ?
C18 C17 H17 114.8 . . ?
N1 C3 C2 127.0(2) . . ?
N1 C3 C4 112.2(2) . . ?
C2 C3 C4 120.8(2) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 111.05(18) . . ?
O1 C7 C6 110.92(19) . . ?
O1 C7 H7 120.6 . . ?
O1 C7 C8 60.32(14) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 109.0(2) . . ?
C8 C7 H7 120.6 . . ?
O5 C4 C3 119.4(2) . . ?
O5 C4 C5 121.0(2) . . ?
C5 C4 C3 119.5(2) . . ?
C12 C11 H11 116.3 . . ?
C12 C11 C10 127.3(2) . . ?
C10 C11 H11 116.3 . . ?
C14 C5 C6 125.9(2) . . ?
C14 C5 C4 119.6(2) . . ?
C4 C5 C6 114.5(2) . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C14 C13 C12 115.01(19) . . ?
H13A C13 H13B 107.5 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
O2 C16 C8 110.04(19) . . ?
O3 C16 O2 122.3(2) . . ?
O3 C16 C8 127.7(2) . . ?
C17 C18 H18 115.8 . . ?
C17 C18 C19 128.4(2) . . ?
C19 C18 H18 115.8 . . ?
N1 C20 H20A 108.7 . . ?
N1 C20 H20B 108.7 . . ?
N1 C20 C19 114.1(2) . . ?
H20A C20 H20B 107.6 . . ?
C19 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C11 C12 C13 122.7(2) . . ?
C11 C12 C15 121.3(2) . . ?
C15 C12 C13 116.0(2) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 C9 111.2(2) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C19 C20 114.19(19) . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
O1 C8 C9 120.54(19) . . ?
O1 C8 C7 58.98(14) . . ?
O1 C8 C16 107.30(19) . . ?
C9 C8 C16 120.4(2) . . ?
C7 C8 C9 129.0(2) . . ?
C7 C8 C16 104.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 C7 C8 C9 -106.0(3) . . . . ?
O1 C7 C8 C16 101.56(19) . . . . ?
O4 C1 C14 C5 -174.1(2) . . . . ?
O4 C1 C14 C13 3.1(3) . . . . ?
O4 C1 C2 C17 2.5(3) . . . . ?
O4 C1 C2 C3 179.3(2) . . . . ?
O2 C6 C7 O1 -62.6(2) . . . . ?
O2 C6 C7 C8 2.0(2) . . . . ?
O2 C6 C5 C14 -66.5(3) . . . . ?
O2 C6 C5 C4 112.8(2) . . . . ?
O2 C16 C8 O1 63.3(2) . . . . ?
O2 C16 C8 C9 -153.6(2) . . . . ?
O2 C16 C8 C7 1.7(2) . . . . ?
O5 C4 C5 C6 -0.2(3) . . . . ?
O5 C4 C5 C14 179.2(2) . . . . ?
O3 C16 C8 O1 -117.4(3) . . . . ?
O3 C16 C8 C9 25.7(4) . . . . ?
O3 C16 C8 C7 -179.0(2) . . . . ?
C1 C14 C5 C6 175.5(2) . . . . ?
C1 C14 C5 C4 -3.7(3) . . . . ?
C1 C14 C13 C12 97.4(2) . . . . ?
C1 C2 C17 C18 177.8(2) . . . . ?
C1 C2 C3 N1 176.2(2) . . . . ?
C1 C2 C3 C4 -6.1(3) . . . . ?
C6 O2 C16 O3 -179.9(2) . . . . ?
C6 O2 C16 C8 -0.5(3) . . . . ?
C6 C7 C8 O1 -103.8(2) . . . . ?
C6 C7 C8 C9 150.2(2) . . . . ?
C6 C7 C8 C16 -2.2(2) . . . . ?
C14 C1 C2 C17 -176.82(18) . . . . ?
C14 C1 C2 C3 0.0(3) . . . . ?
C14 C13 C12 C11 139.5(2) . . . . ?
C14 C13 C12 C15 -42.4(3) . . . . ?
N1 C3 C4 O5 4.2(3) . . . . ?
N1 C3 C4 C5 -174.36(19) . . . . ?
N1 C20 C19 C18 -66.7(3) . . . . ?
C2 C1 C14 C5 5.2(3) . . . . ?
C2 C1 C14 C13 -177.51(19) . . . . ?
C2 C17 C18 C19 2.0(4) . . . . ?
C2 C3 C4 O5 -173.9(2) . . . . ?
C2 C3 C4 C5 7.6(3) . . . . ?
C17 C2 C3 N1 -7.5(4) . . . . ?
C17 C2 C3 C4 170.2(2) . . . . ?
C17 C18 C19 C20 29.2(4) . . . . ?
C3 N1 C20 C19 69.5(3) . . . . ?
C3 C2 C17 C18 1.4(4) . . . . ?
C3 C4 C5 C6 178.33(19) . . . . ?
C3 C4 C5 C14 -2.3(3) . . . . ?
C7 O1 C8 C9 119.9(2) . . . . ?
C7 O1 C8 C16 -97.1(2) . . . . ?
C7 C6 C5 C14 51.9(3) . . . . ?
C7 C6 C5 C4 -128.8(2) . . . . ?
C5 C6 C7 O1 175.87(19) . . . . ?
C5 C6 C7 C8 -119.5(2) . . . . ?
C5 C14 C13 C12 -85.5(3) . . . . ?
C13 C14 C5 C6 -1.4(4) . . . . ?
C13 C14 C5 C4 179.3(2) . . . . ?
C16 O2 C6 C7 -0.9(2) . . . . ?
C16 O2 C6 C5 124.7(2) . . . . ?
C20 N1 C3 C2 -25.8(4) . . . . ?
C20 N1 C3 C4 156.4(2) . . . . ?
C12 C11 C10 C9 -93.7(3) . . . . ?
C10 C9 C8 O1 -149.2(2) . . . . ?
C10 C9 C8 C7 -76.2(3) . . . . ?
C10 C9 C8 C16 72.6(3) . . . . ?
C10 C11 C12 C13 -5.5(4) . . . . ?
C10 C11 C12 C15 176.4(2) . . . . ?
C8 O1 C7 C6 100.6(2) . . . . ?
C8 C9 C10 C11 68.1(2) . . . . ?

_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.821
_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_5895
_database_code_depnum_ccdc_archive 'CCDC 1946367'
loop_
_audit_author_name
_audit_author_address
'Zhaocui Sun'
;Peking Union Medical College and Chinese Academy of Medical Sciences
China
;
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;
_audit_creation_date             2019-04-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            'clavilactone A'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O5'
_chemical_formula_sum            'C16 H14 O5'
_chemical_formula_weight         286.27
_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                   8.5940(3)
_cell_length_b                   11.8962(8)
_cell_length_c                   13.1105(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1340.37(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2898
_cell_measurement_temperature    109.65(10)
_cell_measurement_theta_max      71.0300
_cell_measurement_theta_min      3.7630
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88279
_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    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.981
_diffrn_reflns_theta_min         5.020
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9733
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   56.0000   87.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega   40.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega   62.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega   54.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega  111.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
  7 omega  107.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega   61.00  147.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega    6.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
 12 omega   83.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  -12.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1159411000
_diffrn_orient_matrix_UB_12      0.0272811000
_diffrn_orient_matrix_UB_13      0.0861128000
_diffrn_orient_matrix_UB_21      -0.0341695000
_diffrn_orient_matrix_UB_22      -0.1263447000
_diffrn_orient_matrix_UB_23      0.0131550000
_diffrn_orient_matrix_UB_31      0.1325148000
_diffrn_orient_matrix_UB_32      -0.0086327000
_diffrn_orient_matrix_UB_33      0.0788693000
_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    0.996
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2491
_reflns_number_total             2530
_reflns_odcompleteness_completeness 99.86
_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         0.456
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.090
_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)+(0.0646P)²+0.2780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.0991
_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
O4 O -0.11477(18) -0.31223(14) -0.24457(13) 0.0151(4) Uani 1 1 d . . . . .
C3 C -0.0785(3) -0.32055(19) -0.42577(19) 0.0137(5) Uani 1 1 d . . . . .
H3 H 0.0213 -0.2913 -0.4191 0.016 Uiso 1 1 calc R U . . .
O2 O -0.53401(18) -0.29248(14) -0.25175(13) 0.0125(3) Uani 1 1 d . . . . .
O5 O -0.3415(2) -0.42057(14) -0.62655(12) 0.0166(4) Uani 1 1 d . . . . .
O3 O -0.79073(18) -0.27120(14) -0.25012(13) 0.0143(4) Uani 1 1 d . . . . .
C1 C -0.2850(3) -0.39120(19) -0.53142(18) 0.0136(5) Uani 1 1 d . . . . .
C2 C -0.1362(3) -0.34728(19) -0.52161(18) 0.0131(5) Uani 1 1 d . . . . .
H2 H -0.0751 -0.3358 -0.5792 0.016 Uiso 1 1 calc R U . . .
O1 O -0.5881(2) -0.47767(14) -0.13217(13) 0.0164(4) Uani 1 1 d . . . . .
C14 C -0.3812(3) -0.40641(18) -0.44631(18) 0.0114(5) Uani 1 1 d . . . . .
C16 C -0.6783(3) -0.33277(19) -0.24300(16) 0.0122(5) Uani 1 1 d . . . . .
C5 C -0.3221(3) -0.37912(18) -0.34912(17) 0.0115(5) Uani 1 1 d . . . . .
C9 C -0.8131(3) -0.53106(19) -0.2493(2) 0.0161(5) Uani 1 1 d . . . . .
H9A H -0.9066 -0.4956 -0.2232 0.019 Uiso 1 1 calc R U . . .
H9B H -0.8010 -0.6027 -0.2148 0.019 Uiso 1 1 calc R U . . .
C4 C -0.1698(3) -0.33757(18) -0.34000(17) 0.0120(5) Uani 1 1 d . . . . .
C7 C -0.5109(3) -0.4885(2) -0.22946(17) 0.0141(5) Uani 1 1 d . . . . .
H7 H -0.4780 -0.5623 -0.2547 0.017 Uiso 1 1 calc R U . . .
C8 C -0.6762(3) -0.4583(2) -0.22537(17) 0.0136(5) Uani 1 1 d . . . . .
C6 C -0.4156(3) -0.38478(19) -0.25175(17) 0.0125(4) Uani 1 1 d . . . . .
H6 H -0.3447 -0.3723 -0.1943 0.015 Uiso 1 1 calc R U . . .
C10 C -0.8327(3) -0.5522(2) -0.3649(2) 0.0167(5) Uani 1 1 d . . . . .
H10A H -0.9285 -0.5933 -0.3765 0.020 Uiso 1 1 calc R U . . .
H10B H -0.8411 -0.4805 -0.3998 0.020 Uiso 1 1 calc R U . . .
C13 C -0.5458(3) -0.4487(2) -0.46418(17) 0.0128(5) Uani 1 1 d . . . . .
H13A H -0.5763 -0.4289 -0.5331 0.015 Uiso 1 1 calc R U . . .
H13B H -0.6150 -0.4095 -0.4179 0.015 Uiso 1 1 calc R U . . .
C12 C -0.5698(3) -0.57526(19) -0.45009(17) 0.0135(5) Uani 1 1 d . . . . .
C11 C -0.6991(3) -0.6173(2) -0.40930(18) 0.0163(5) Uani 1 1 d . . . . .
H11 H -0.7077 -0.6952 -0.4081 0.020 Uiso 1 1 calc R U . . .
C15 C -0.4401(3) -0.6498(2) -0.4869(2) 0.0194(6) Uani 1 1 d . . . . .
H15A H -0.3488 -0.6369 -0.4463 0.029 Uiso 1 1 calc R U . . .
H15B H -0.4176 -0.6329 -0.5570 0.029 Uiso 1 1 calc R U . . .
H15C H -0.4709 -0.7270 -0.4809 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.388(3) . ?
C3 C4 1.386(3) . ?
O2 C16 1.335(3) . ?
O2 C6 1.497(3) . ?
O5 C1 1.383(3) . ?
O3 C16 1.216(3) . ?
C1 C2 1.388(3) . ?
C1 C14 1.400(3) . ?
C2 H2 0.9300 . ?
O1 C7 1.444(3) . ?
O1 C8 1.456(3) . ?
C14 C5 1.410(3) . ?
C14 C13 1.519(3) . ?
C16 C8 1.511(3) . ?
C5 C4 1.404(3) . ?
C5 C6 1.510(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.494(3) . ?
C9 C10 1.546(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.467(3) . ?
C7 C6 1.509(3) . ?
C6 H6 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.531(3) . ?
C12 C11 1.331(3) . ?
C12 C15 1.504(3) . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C16 O2 C6 111.61(18) . . ?
O5 C1 C2 120.1(2) . . ?
O5 C1 C14 118.6(2) . . ?
C2 C1 C14 121.3(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C7 O1 C8 60.78(14) . . ?
C1 C14 C5 118.5(2) . . ?
C1 C14 C13 118.0(2) . . ?
C5 C14 C13 123.4(2) . . ?
O2 C16 C8 110.9(2) . . ?
O3 C16 O2 121.0(2) . . ?
O3 C16 C8 128.1(2) . . ?
C14 C5 C6 124.2(2) . . ?
C4 C5 C14 119.6(2) . . ?
C4 C5 C6 116.1(2) . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.7(2) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
O4 C4 C3 120.8(2) . . ?
O4 C4 C5 118.5(2) . . ?
C3 C4 C5 120.7(2) . . ?
O1 C7 H7 120.7 . . ?
O1 C7 C8 60.03(14) . . ?
O1 C7 C6 110.35(19) . . ?
C8 C7 H7 120.7 . . ?
C8 C7 C6 109.4(2) . . ?
C6 C7 H7 120.7 . . ?
O1 C8 C16 106.92(19) . . ?
O1 C8 C9 119.61(19) . . ?
O1 C8 C7 59.19(14) . . ?
C9 C8 C16 122.1(2) . . ?
C7 C8 C16 104.3(2) . . ?
C7 C8 C9 127.8(2) . . ?
O2 C6 C5 109.21(17) . . ?
O2 C6 C7 103.34(18) . . ?
O2 C6 H6 108.2 . . ?
C5 C6 H6 108.2 . . ?
C7 C6 C5 119.27(19) . . ?
C7 C6 H6 108.2 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 112.3(2) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C14 C13 C12 115.65(19) . . ?
H13A C13 H13B 107.4 . . ?
C12 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C11 C12 C13 122.1(2) . . ?
C11 C12 C15 121.8(2) . . ?
C15 C12 C13 116.2(2) . . ?
C10 C11 H11 116.6 . . ?
C12 C11 C10 126.9(2) . . ?
C12 C11 H11 116.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C16 C8 O1 59.1(2) . . . . ?
O2 C16 C8 C9 -157.7(2) . . . . ?
O2 C16 C8 C7 -2.5(3) . . . . ?
O5 C1 C2 C3 -178.4(2) . . . . ?
O5 C1 C14 C5 178.4(2) . . . . ?
O5 C1 C14 C13 -3.2(3) . . . . ?
O3 C16 C8 O1 -121.5(2) . . . . ?
O3 C16 C8 C9 21.6(4) . . . . ?
O3 C16 C8 C7 176.8(2) . . . . ?
C1 C14 C5 C4 0.1(3) . . . . ?
C1 C14 C5 C6 176.2(2) . . . . ?
C1 C14 C13 C12 97.2(2) . . . . ?
C2 C3 C4 O4 179.7(2) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C1 C14 C5 -1.8(3) . . . . ?
C2 C1 C14 C13 176.6(2) . . . . ?
O1 C7 C8 C16 101.37(19) . . . . ?
O1 C7 C8 C9 -105.4(3) . . . . ?
O1 C7 C6 O2 -59.9(2) . . . . ?
O1 C7 C6 C5 178.78(19) . . . . ?
C14 C1 C2 C3 1.9(3) . . . . ?
C14 C5 C4 O4 -179.6(2) . . . . ?
C14 C5 C4 C3 1.6(3) . . . . ?
C14 C5 C6 O2 -70.5(3) . . . . ?
C14 C5 C6 C7 47.9(3) . . . . ?
C14 C13 C12 C11 143.0(2) . . . . ?
C14 C13 C12 C15 -38.2(3) . . . . ?
C16 O2 C6 C5 121.8(2) . . . . ?
C16 O2 C6 C7 -6.2(2) . . . . ?
C5 C14 C13 C12 -84.5(3) . . . . ?
C9 C10 C11 C12 -91.1(3) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C4 C5 C6 O2 105.8(2) . . . . ?
C4 C5 C6 C7 -135.8(2) . . . . ?
C7 O1 C8 C16 -96.9(2) . . . . ?
C7 O1 C8 C9 118.9(2) . . . . ?
C8 O1 C7 C6 101.3(2) . . . . ?
C8 C9 C10 C11 64.4(3) . . . . ?
C8 C7 C6 O2 4.4(2) . . . . ?
C8 C7 C6 C5 -117.0(2) . . . . ?
C6 O2 C16 O3 -173.8(2) . . . . ?
C6 O2 C16 C8 5.6(2) . . . . ?
C6 C5 C4 O4 3.9(3) . . . . ?
C6 C5 C4 C3 -174.9(2) . . . . ?
C6 C7 C8 O1 -102.8(2) . . . . ?
C6 C7 C8 C16 -1.5(2) . . . . ?
C6 C7 C8 C9 151.8(2) . . . . ?
C10 C9 C8 O1 -145.8(2) . . . . ?
C10 C9 C8 C16 75.5(3) . . . . ?
C10 C9 C8 C7 -73.5(3) . . . . ?
C13 C14 C5 C4 -178.2(2) . . . . ?
C13 C14 C5 C6 -2.1(3) . . . . ?
C13 C12 C11 C10 -4.7(4) . . . . ?
C15 C12 C11 C10 176.6(2) . . . . ?

_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.809
_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.
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ????'
_chemical_compound_source        'Clitocybe Clavipes'
_chemical_properties_physical    Oxygen-sensitive
