# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_5907
_database_code_depnum_ccdc_archive 'CCDC 1909884'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Peking Union Medical College
China
;
_audit_update_record             
;
2019-04-13 deposited with the CCDC.	2019-09-16 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         'C24 H14 O3'
_chemical_formula_sum            'C24 H14 O3'
_chemical_formula_weight         350.35
_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 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.2754(16)
_cell_length_b                   13.4235(13)
_cell_length_c                   9.5478(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.807(10)
_cell_angle_gamma                90.00
_cell_volume                     1697.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1267
_cell_measurement_temperature    108.00(14)
_cell_measurement_theta_max      28.5150
_cell_measurement_theta_min      3.9580
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97354
_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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7974
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8401
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    0.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   26.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   86.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00   81.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega   66.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -23.00   11.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000   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      0.0528358000
_diffrn_orient_matrix_UB_12      0.0079562000
_diffrn_orient_matrix_UB_13      0.0012008000
_diffrn_orient_matrix_UB_21      -0.0038231000
_diffrn_orient_matrix_UB_22      0.0366218000
_diffrn_orient_matrix_UB_23      0.0529051000
_diffrn_orient_matrix_UB_31      0.0075482000
_diffrn_orient_matrix_UB_32      -0.0372039000
_diffrn_orient_matrix_UB_33      0.0523520000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2354
_reflns_number_total             3343
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0319P)²+0.1337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1104
_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
O3 O 0.47945(11) 0.14572(11) 0.21389(13) 0.0251(4) Uani 1 1 d . . .
O1 O 0.21673(10) 0.17117(10) 0.61708(13) 0.0195(3) Uani 1 1 d . . .
O2 O 0.41706(11) 0.32519(11) 0.30288(14) 0.0283(4) Uani 1 1 d . . .
C8 C 0.32628(14) 0.06106(15) 0.49298(19) 0.0176(5) Uani 1 1 d . . .
C7 C 0.39141(15) 0.05504(16) 0.38157(19) 0.0190(5) Uani 1 1 d . . .
C3 C 0.31345(15) 0.24836(15) 0.46671(19) 0.0176(5) Uani 1 1 d . . .
C13 C 0.11598(15) 0.29946(16) 0.71311(19) 0.0188(5) Uani 1 1 d . . .
C5 C 0.38577(15) 0.25088(16) 0.3589(2) 0.0195(5) Uani 1 1 d . . .
C1 C 0.19416(15) 0.27259(16) 0.61835(19) 0.0188(5) Uani 1 1 d . . .
C4 C 0.28912(15) 0.15914(16) 0.52423(19) 0.0178(5) Uani 1 1 d . . .
C23 C 0.14314(16) 0.57484(16) 0.42489(19) 0.0227(5) Uani 1 1 d . . .
H23 H 0.0802 0.6033 0.4028 0.027 Uiso 1 1 calc R . .
C12 C 0.42769(15) -0.03701(16) 0.3428(2) 0.0222(5) Uani 1 1 d . . .
H12 H 0.4701 -0.0413 0.2693 0.027 Uiso 1 1 calc R . .
C24 C 0.15040(16) 0.47424(16) 0.45765(19) 0.0205(5) Uani 1 1 d . . .
H24 H 0.0922 0.4356 0.4571 0.025 Uiso 1 1 calc R . .
C10 C 0.33886(16) -0.11620(16) 0.5238(2) 0.0244(5) Uani 1 1 d . . .
H10 H 0.3221 -0.1736 0.5716 0.029 Uiso 1 1 calc R . .
C9 C 0.30118(15) -0.02498(15) 0.5643(2) 0.0210(5) Uani 1 1 d . . .
H9 H 0.2594 -0.0213 0.6386 0.025 Uiso 1 1 calc R . .
C6 C 0.42337(15) 0.14701(16) 0.31037(19) 0.0197(5) Uani 1 1 d . . .
C19 C 0.24433(15) 0.43047(15) 0.49145(19) 0.0179(5) Uani 1 1 d . . .
C22 C 0.22930(16) 0.63299(16) 0.4251(2) 0.0241(5) Uani 1 1 d . . .
H22 H 0.2243 0.7004 0.4030 0.029 Uiso 1 1 calc R . .
C11 C 0.40130(16) -0.12321(17) 0.4128(2) 0.0253(5) Uani 1 1 d . . .
H11 H 0.4252 -0.1849 0.3856 0.030 Uiso 1 1 calc R . .
C18 C 0.04361(15) 0.22990(17) 0.7471(2) 0.0240(5) Uani 1 1 d . . .
H18 H 0.0452 0.1661 0.7095 0.029 Uiso 1 1 calc R . .
C20 C 0.33061(16) 0.49003(16) 0.49031(19) 0.0218(5) Uani 1 1 d . . .
H20 H 0.3939 0.4620 0.5113 0.026 Uiso 1 1 calc R . .
C14 C 0.11307(15) 0.39460(17) 0.77239(19) 0.0222(5) Uani 1 1 d . . .
H14 H 0.1611 0.4418 0.7516 0.027 Uiso 1 1 calc R . .
C2 C 0.25096(15) 0.32310(16) 0.52688(19) 0.0187(5) Uani 1 1 d . . .
C17 C -0.03095(17) 0.25467(18) 0.8365(2) 0.0286(6) Uani 1 1 d . . .
H17 H -0.0792 0.2077 0.8578 0.034 Uiso 1 1 calc R . .
C21 C 0.32276(17) 0.59046(16) 0.4581(2) 0.0237(5) Uani 1 1 d . . .
H21 H 0.3807 0.6295 0.4588 0.028 Uiso 1 1 calc R . .
C15 C 0.03862(16) 0.41877(18) 0.8622(2) 0.0303(6) Uani 1 1 d . . .
H15 H 0.0373 0.4822 0.9013 0.036 Uiso 1 1 calc R . .
C16 C -0.03338(17) 0.34954(19) 0.8940(2) 0.0302(6) Uani 1 1 d . . .
H16 H -0.0833 0.3664 0.9536 0.036 Uiso 1 1 calc R . .


_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
O3 C6 1.222(2) . ?
O1 C1 1.394(2) . ?
O1 C4 1.360(2) . ?
O2 C5 1.218(2) . ?
C8 C7 1.417(3) . ?
C8 C4 1.444(3) . ?
C8 C9 1.393(3) . ?
C7 C12 1.385(3) . ?
C7 C6 1.485(3) . ?
C3 C5 1.454(3) . ?
C3 C4 1.365(3) . ?
C3 C2 1.445(3) . ?
C13 C1 1.467(3) . ?
C13 C18 1.393(3) . ?
C13 C14 1.398(3) . ?
C5 C6 1.562(3) . ?
C1 C2 1.371(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.388(3) . ?
C23 C22 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.393(3) . ?
C24 H24 0.9300 . ?
C24 C19 1.397(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.388(3) . ?
C10 C11 1.391(3) . ?
C9 H9 0.9300 . ?
C19 C20 1.397(3) . ?
C19 C2 1.482(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(3) . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.389(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.388(3) . ?
C21 H21 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 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
C4 O1 C1 106.45(15) . . ?
C7 C8 C4 116.17(18) . . ?
C9 C8 C7 119.85(19) . . ?
C9 C8 C4 123.98(17) . . ?
C8 C7 C6 120.23(19) . . ?
C12 C7 C8 119.45(19) . . ?
C12 C7 C6 120.29(17) . . ?
C4 C3 C5 119.35(18) . . ?
C4 C3 C2 106.96(17) . . ?
C2 C3 C5 133.54(19) . . ?
C18 C13 C1 120.40(19) . . ?
C18 C13 C14 118.66(18) . . ?
C14 C13 C1 120.94(19) . . ?
O2 C5 C3 126.20(19) . . ?
O2 C5 C6 118.42(16) . . ?
C3 C5 C6 115.37(18) . . ?
O1 C1 C13 114.01(17) . . ?
C2 C1 O1 110.49(17) . . ?
C2 C1 C13 135.50(19) . . ?
O1 C4 C8 120.60(18) . . ?
O1 C4 C3 110.75(18) . . ?
C3 C4 C8 128.57(17) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(2) . . ?
C7 C12 H12 119.7 . . ?
C7 C12 C11 120.66(18) . . ?
C11 C12 H12 119.7 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C19 120.6(2) . . ?
C19 C24 H24 119.7 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.53(18) . . ?
C10 C9 H9 120.2 . . ?
O3 C6 C7 122.70(19) . . ?
O3 C6 C5 117.31(18) . . ?
C7 C6 C5 119.99(16) . . ?
C24 C19 C20 118.5(2) . . ?
C24 C19 C2 120.03(19) . . ?
C20 C19 C2 121.46(19) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 H22 120.1 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C3 C2 C19 127.70(17) . . ?
C1 C2 C3 105.34(18) . . ?
C1 C2 C19 126.86(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.0 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 H16 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 C1 C2 C3 -0.8(2) . . . . ?
O1 C1 C2 C19 175.75(18) . . . . ?
O2 C5 C6 O3 -3.0(3) . . . . ?
O2 C5 C6 C7 176.61(18) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C7 C6 O3 179.96(18) . . . . ?
C8 C7 C6 C5 0.4(3) . . . . ?
C7 C8 C4 O1 171.84(17) . . . . ?
C7 C8 C4 C3 -4.7(3) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C7 C12 C11 C10 -0.8(3) . . . . ?
C3 C5 C6 O3 175.64(18) . . . . ?
C3 C5 C6 C7 -4.8(3) . . . . ?
C13 C1 C2 C3 -179.6(2) . . . . ?
C13 C1 C2 C19 -3.0(4) . . . . ?
C13 C18 C17 C16 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C5 C3 C4 O1 -176.73(16) . . . . ?
C5 C3 C4 C8 0.1(3) . . . . ?
C5 C3 C2 C1 176.2(2) . . . . ?
C5 C3 C2 C19 -0.2(4) . . . . ?
C1 O1 C4 C8 -177.07(17) . . . . ?
C1 O1 C4 C3 0.0(2) . . . . ?
C1 C13 C18 C17 -179.83(18) . . . . ?
C1 C13 C14 C15 -179.85(18) . . . . ?
C4 O1 C1 C13 179.55(15) . . . . ?
C4 O1 C1 C2 0.5(2) . . . . ?
C4 C8 C7 C12 -178.11(18) . . . . ?
C4 C8 C7 C6 4.0(3) . . . . ?
C4 C8 C9 C10 178.32(19) . . . . ?
C4 C3 C5 O2 -177.0(2) . . . . ?
C4 C3 C5 C6 4.5(3) . . . . ?
C4 C3 C2 C1 0.8(2) . . . . ?
C4 C3 C2 C19 -175.72(19) . . . . ?
C23 C24 C19 C20 -0.5(3) . . . . ?
C23 C24 C19 C2 179.71(17) . . . . ?
C23 C22 C21 C20 0.3(3) . . . . ?
C12 C7 C6 O3 2.1(3) . . . . ?
C12 C7 C6 C5 -177.41(18) . . . . ?
C24 C23 C22 C21 0.0(3) . . . . ?
C24 C19 C20 C21 0.8(3) . . . . ?
C24 C19 C2 C3 128.0(2) . . . . ?
C24 C19 C2 C1 -47.8(3) . . . . ?
C9 C8 C7 C12 1.4(3) . . . . ?
C9 C8 C7 C6 -176.43(17) . . . . ?
C9 C8 C4 O1 -7.7(3) . . . . ?
C9 C8 C4 C3 175.8(2) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C6 C7 C12 C11 177.41(18) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C22 C23 C24 C19 0.2(3) . . . . ?
C11 C10 C9 C8 -0.1(3) . . . . ?
C18 C13 C1 O1 -26.3(3) . . . . ?
C18 C13 C1 C2 152.5(2) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
C18 C17 C16 C15 -0.2(3) . . . . ?
C20 C19 C2 C3 -51.8(3) . . . . ?
C20 C19 C2 C1 132.5(2) . . . . ?
C14 C13 C1 O1 152.95(18) . . . . ?
C14 C13 C1 C2 -28.3(3) . . . . ?
C14 C13 C18 C17 0.9(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C2 C3 C5 O2 8.0(4) . . . . ?
C2 C3 C5 C6 -170.5(2) . . . . ?
C2 C3 C4 O1 -0.5(2) . . . . ?
C2 C3 C4 C8 176.31(19) . . . . ?
C2 C19 C20 C21 -179.42(17) . . . . ?

####################################################################### 
# 
# 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_c256
_database_code_depnum_ccdc_archive 'CCDC 876846'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Peking Union Medical College
China
;
_audit_update_record             
;
2019-04-13 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H24 O3'
_chemical_formula_weight         528.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4942(8)
_cell_length_b                   10.2513(9)
_cell_length_c                   15.9443(15)
_cell_angle_alpha                94.8310(10)
_cell_angle_beta                 96.6810(10)
_cell_angle_gamma                104.8190(10)
_cell_volume                     1323.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9118
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.37

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17382
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6076
_reflns_number_gt                5402
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.4507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6076
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55582(11) 1.06474(9) 0.82986(6) 0.0248(2) Uani 1 1 d . . .
O2 O 0.27985(10) 0.87486(8) 0.74519(5) 0.01707(18) Uani 1 1 d . . .
O3 O 0.37991(11) 0.56264(8) 0.92502(5) 0.02145(19) Uani 1 1 d . . .
C1 C 0.60810(14) 0.91593(11) 0.93012(7) 0.0168(2) Uani 1 1 d . . .
C2 C 0.74159(15) 1.01327(12) 0.97725(8) 0.0208(2) Uani 1 1 d . . .
H2 H 0.7738 1.1022 0.9609 0.025 Uiso 1 1 calc R . .
C3 C 0.82742(15) 0.98001(13) 1.04820(8) 0.0233(3) Uani 1 1 d . . .
H3 H 0.9185 1.0461 1.0804 0.028 Uiso 1 1 calc R . .
C4 C 0.78012(16) 0.85015(13) 1.07209(8) 0.0230(3) Uani 1 1 d . . .
H4 H 0.8392 0.8278 1.1207 0.028 Uiso 1 1 calc R . .
C5 C 0.64692(15) 0.75258(12) 1.02547(7) 0.0200(2) Uani 1 1 d . . .
H5 H 0.6151 0.6640 1.0423 0.024 Uiso 1 1 calc R . .
C6 C 0.56016(14) 0.78480(11) 0.95416(7) 0.0169(2) Uani 1 1 d . . .
C7 C 0.41834(14) 0.67701(11) 0.90420(7) 0.0163(2) Uani 1 1 d . . .
C8 C 0.32967(14) 0.71705(11) 0.83096(7) 0.0162(2) Uani 1 1 d . . .
C9 C 0.37409(14) 0.84457(11) 0.81044(7) 0.0162(2) Uani 1 1 d . . .
C10 C 0.51752(14) 0.95370(11) 0.85452(7) 0.0172(2) Uani 1 1 d . . .
C12 C 0.15105(14) 0.74930(11) 0.71202(7) 0.0162(2) Uani 1 1 d . . .
C13 C 0.20122(14) 0.66682(11) 0.64213(7) 0.0165(2) Uani 1 1 d . . .
C14 C 0.21523(14) 0.56557(11) 0.68919(7) 0.0167(2) Uani 1 1 d . . .
C15 C 0.17859(14) 0.63468(11) 0.77121(7) 0.0160(2) Uani 1 1 d . . .
C16 C -0.01254(14) 0.78061(12) 0.70019(7) 0.0177(2) Uani 1 1 d . . .
C17 C -0.03095(15) 0.90615(12) 0.73064(8) 0.0211(2) Uani 1 1 d . . .
H17 H 0.0620 0.9750 0.7588 0.025 Uiso 1 1 calc R . .
C18 C -0.18457(17) 0.93153(14) 0.72007(8) 0.0264(3) Uani 1 1 d . . .
H18 H -0.1962 1.0175 0.7412 0.032 Uiso 1 1 calc R . .
C19 C -0.32088(16) 0.83199(15) 0.67891(9) 0.0288(3) Uani 1 1 d . . .
H19 H -0.4259 0.8495 0.6716 0.035 Uiso 1 1 calc R . .
C20 C -0.30306(17) 0.70670(15) 0.64841(9) 0.0310(3) Uani 1 1 d . . .
H20 H -0.3964 0.6380 0.6204 0.037 Uiso 1 1 calc R . .
C21 C -0.14992(16) 0.68095(13) 0.65845(8) 0.0251(3) Uani 1 1 d . . .
H21 H -0.1386 0.5951 0.6368 0.030 Uiso 1 1 calc R . .
C22 C 0.23499(14) 0.70712(11) 0.55874(7) 0.0174(2) Uani 1 1 d . . .
C23 C 0.19911(16) 0.82543(12) 0.53466(8) 0.0220(2) Uani 1 1 d . . .
H23 H 0.1458 0.8736 0.5705 0.026 Uiso 1 1 calc R . .
C24 C 0.24041(18) 0.87340(13) 0.45913(8) 0.0266(3) Uani 1 1 d . . .
H24 H 0.2156 0.9542 0.4437 0.032 Uiso 1 1 calc R . .
C25 C 0.31751(17) 0.80408(14) 0.40639(8) 0.0263(3) Uani 1 1 d . . .
H25 H 0.3469 0.8376 0.3550 0.032 Uiso 1 1 calc R . .
C26 C 0.35190(16) 0.68517(13) 0.42864(8) 0.0246(3) Uani 1 1 d . . .
H26 H 0.4037 0.6368 0.3920 0.029 Uiso 1 1 calc R . .
C27 C 0.31110(15) 0.63683(12) 0.50388(8) 0.0208(2) Uani 1 1 d . . .
H27 H 0.3349 0.5553 0.5185 0.025 Uiso 1 1 calc R . .
C28 C 0.24651(14) 0.43209(12) 0.67383(8) 0.0183(2) Uani 1 1 d . . .
C29 C 0.32881(16) 0.38091(13) 0.73880(8) 0.0238(3) Uani 1 1 d . . .
H29 H 0.3694 0.4347 0.7922 0.029 Uiso 1 1 calc R . .
C30 C 0.35173(17) 0.25196(13) 0.72591(9) 0.0265(3) Uani 1 1 d . . .
H30 H 0.4085 0.2181 0.7704 0.032 Uiso 1 1 calc R . .
C31 C 0.29238(17) 0.17254(13) 0.64876(9) 0.0276(3) Uani 1 1 d . . .
H31 H 0.3088 0.0844 0.6402 0.033 Uiso 1 1 calc R . .
C32 C 0.20891(17) 0.22127(13) 0.58383(9) 0.0285(3) Uani 1 1 d . . .
H32 H 0.1680 0.1665 0.5308 0.034 Uiso 1 1 calc R . .
C33 C 0.18507(16) 0.35017(13) 0.59633(8) 0.0235(3) Uani 1 1 d . . .
H33 H 0.1267 0.3829 0.5520 0.028 Uiso 1 1 calc R . .
C34 C 0.03839(14) 0.55986(12) 0.81353(7) 0.0177(2) Uani 1 1 d . . .
C35 C 0.00562(16) 0.61778(13) 0.88954(8) 0.0234(3) Uani 1 1 d . . .
H35 H 0.0739 0.7037 0.9152 0.028 Uiso 1 1 calc R . .
C36 C -0.12536(17) 0.55155(15) 0.92818(9) 0.0286(3) Uani 1 1 d . . .
H36 H -0.1464 0.5921 0.9800 0.034 Uiso 1 1 calc R . .
C37 C -0.22555(17) 0.42630(15) 0.89119(9) 0.0311(3) Uani 1 1 d . . .
H37 H -0.3155 0.3807 0.9175 0.037 Uiso 1 1 calc R . .
C38 C -0.19399(18) 0.36800(15) 0.81592(9) 0.0328(3) Uani 1 1 d . . .
H38 H -0.2624 0.2820 0.7906 0.039 Uiso 1 1 calc R . .
C39 C -0.06295(16) 0.43414(13) 0.77697(8) 0.0258(3) Uani 1 1 d . . .
H39 H -0.0425 0.3932 0.7251 0.031 Uiso 1 1 calc R . .


_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 C10 1.2133(14) . ?
O2 C9 1.3444(14) . ?
O2 C12 1.4710(13) . ?
O3 C7 1.2191(14) . ?
C1 C2 1.3939(16) . ?
C1 C6 1.4011(16) . ?
C1 C10 1.4865(16) . ?
C2 C3 1.3884(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3878(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3904(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3920(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5014(16) . ?
C7 C8 1.4607(15) . ?
C8 C9 1.3442(16) . ?
C8 C15 1.5144(15) . ?
C9 C10 1.4835(16) . ?
C12 C16 1.4990(16) . ?
C12 C13 1.5082(15) . ?
C12 C15 1.6130(15) . ?
C13 C14 1.3520(16) . ?
C13 C22 1.4634(16) . ?
C14 C28 1.4654(16) . ?
C14 C15 1.5364(15) . ?
C15 C34 1.5063(16) . ?
C16 C17 1.3898(17) . ?
C16 C21 1.3940(17) . ?
C17 C18 1.3887(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3862(19) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.3969(17) . ?
C22 C27 1.4021(16) . ?
C23 C24 1.3874(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3808(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.3886(18) . ?
C25 H25 0.9500 . ?
C26 C27 1.3835(17) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.3955(17) . ?
C28 C33 1.3984(17) . ?
C29 C30 1.3866(18) . ?
C29 H29 0.9500 . ?
C30 C31 1.381(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.3888(18) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C39 1.3896(17) . ?
C34 C35 1.3930(17) . ?
C35 C36 1.3863(18) . ?
C35 H35 0.9500 . ?
C36 C37 1.385(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.380(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.3894(18) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?

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
C9 O2 C12 106.72(8) . . ?
C2 C1 C6 120.23(11) . . ?
C2 C1 C10 119.01(10) . . ?
C6 C1 C10 120.76(10) . . ?
C3 C2 C1 119.84(11) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.99(11) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.49(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.98(11) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.46(11) . . ?
C5 C6 C7 118.92(10) . . ?
C1 C6 C7 121.62(10) . . ?
O3 C7 C8 122.49(11) . . ?
O3 C7 C6 120.88(10) . . ?
C8 C7 C6 116.63(10) . . ?
C9 C8 C7 120.93(10) . . ?
C9 C8 C15 109.85(10) . . ?
C7 C8 C15 129.16(10) . . ?
C8 C9 O2 117.00(10) . . ?
C8 C9 C10 125.07(10) . . ?
O2 C9 C10 117.93(10) . . ?
O1 C10 C9 121.65(11) . . ?
O1 C10 C1 123.48(11) . . ?
C9 C10 C1 114.87(10) . . ?
O2 C12 C16 109.15(9) . . ?
O2 C12 C13 112.28(9) . . ?
C16 C12 C13 120.37(9) . . ?
O2 C12 C15 106.91(8) . . ?
C16 C12 C15 119.85(9) . . ?
C13 C12 C15 86.21(8) . . ?
C14 C13 C22 138.32(11) . . ?
C14 C13 C12 94.65(9) . . ?
C22 C13 C12 126.70(10) . . ?
C13 C14 C28 136.02(11) . . ?
C13 C14 C15 95.06(9) . . ?
C28 C14 C15 128.88(10) . . ?
C34 C15 C8 115.42(9) . . ?
C34 C15 C14 118.79(9) . . ?
C8 C15 C14 114.61(9) . . ?
C34 C15 C12 119.26(9) . . ?
C8 C15 C12 99.49(8) . . ?
C14 C15 C12 83.87(8) . . ?
C17 C16 C21 119.17(11) . . ?
C17 C16 C12 121.59(11) . . ?
C21 C16 C12 119.23(10) . . ?
C18 C17 C16 120.35(12) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.28(12) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.56(12) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.43(13) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.20(12) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C23 C22 C27 118.28(11) . . ?
C23 C22 C13 118.71(11) . . ?
C27 C22 C13 122.89(11) . . ?
C24 C23 C22 120.83(12) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.19(12) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.80(12) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.29(12) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 120.60(11) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C29 C28 C33 118.86(11) . . ?
C29 C28 C14 120.14(11) . . ?
C33 C28 C14 120.86(11) . . ?
C30 C29 C28 120.39(12) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C31 C30 C29 120.28(12) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.08(12) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C33 119.97(12) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C28 120.40(12) . . ?
C32 C33 H33 119.8 . . ?
C28 C33 H33 119.8 . . ?
C39 C34 C35 118.72(11) . . ?
C39 C34 C15 121.09(11) . . ?
C35 C34 C15 120.17(10) . . ?
C36 C35 C34 120.81(12) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C37 C36 C35 120.00(12) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C38 C37 C36 119.63(12) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C37 C38 C39 120.53(13) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C38 C39 C34 120.31(12) . . ?
C38 C39 H39 119.8 . . ?
C34 C39 H39 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_5804
_database_code_depnum_ccdc_archive 'CCDC 1909889'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Peking Union Medical College
China
;
_audit_update_record             
;
2019-04-13 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H15 Cl F3 N O6, C H2 Cl2'
_chemical_formula_sum            'C27 H17 Cl3 F3 N O6'
_chemical_formula_weight         614.77
_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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   6.9362(5)
_cell_length_b                   16.8867(11)
_cell_length_c                   21.0716(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2468.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2592
_cell_measurement_temperature    110.60(14)
_cell_measurement_theta_max      27.0440
_cell_measurement_theta_min      3.5100
_exptl_absorpt_coefficient_mu    0.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90703
_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    1.654
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12224
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.09
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.60(14)
_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 0.8469
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   47.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   28.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   37.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega  -72.00  -15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -57.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   37.00   71.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   53.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4210  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4210   19.0000   30.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0405391000
_diffrn_orient_matrix_UB_12      -0.0238416000
_diffrn_orient_matrix_UB_13      -0.0242880000
_diffrn_orient_matrix_UB_21      0.0069698000
_diffrn_orient_matrix_UB_22      0.0321744000
_diffrn_orient_matrix_UB_23      -0.0214957000
_diffrn_orient_matrix_UB_31      0.0936361000
_diffrn_orient_matrix_UB_32      -0.0127147000
_diffrn_orient_matrix_UB_33      -0.0089151000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4182
_reflns_number_total             4844
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.385
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0518
_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     
'calc w=1/[σ²(Fo²)+(0.0589P)²+1.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1266
_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
Cl1 Cl -0.89401(14) -0.79500(6) -0.16922(4) 0.0293(2) Uani 1 1 d . . .
F1 F -1.4193(3) -0.99269(13) -0.22403(10) 0.0262(5) Uani 1 1 d . . .
F3 F -1.6795(3) -0.94816(14) -0.26438(11) 0.0306(6) Uani 1 1 d . . .
O2 O -1.5504(4) -0.89694(14) -0.36681(11) 0.0170(5) Uani 1 1 d . . .
O4 O -0.9642(4) -1.04120(15) -0.37555(12) 0.0247(6) Uani 1 1 d . . .
O5 O -0.6605(4) -1.09782(17) -0.43433(14) 0.0361(7) Uani 1 1 d . . .
O3 O -1.1390(4) -1.04836(17) -0.28952(13) 0.0329(7) Uani 1 1 d . . .
N1 N -1.6248(4) -0.77846(17) -0.31439(14) 0.0179(6) Uani 1 1 d . . .
O6 O -1.1289(4) -0.90960(16) -0.56359(12) 0.0252(6) Uani 1 1 d . . .
C9 C -1.0065(5) -0.9393(2) -0.53001(17) 0.0181(8) Uani 1 1 d . . .
F2 F -1.5386(4) -1.04724(13) -0.30857(10) 0.0309(6) Uani 1 1 d . . .
C3 C -1.1947(5) -0.9201(2) -0.42433(16) 0.0161(7) Uani 1 1 d . . .
C4 C -1.0416(5) -0.9577(2) -0.46138(17) 0.0179(7) Uani 1 1 d . . .
C1 C -1.1193(6) -1.0166(2) -0.33978(17) 0.0224(8) Uani 1 1 d . . .
C24 C -1.6717(5) -0.8344(2) -0.35800(17) 0.0195(8) Uani 1 1 d . . .
C20 C -1.3910(6) -0.7178(2) -0.24283(17) 0.0247(8) Uani 1 1 d . . .
H20 H -1.4694 -0.6717 -0.2405 0.030 Uiso 1 1 calc R . .
C21 C -1.2193(6) -0.7208(2) -0.20942(18) 0.0257(9) Uani 1 1 d . . .
H21 H -1.1793 -0.6769 -0.1844 0.031 Uiso 1 1 calc R . .
O1 O -1.8144(4) -0.83239(15) -0.39093(13) 0.0252(6) Uani 1 1 d . . .
C26 C -1.5068(6) -0.9788(2) -0.27911(18) 0.0233(8) Uani 1 1 d . . .
C7 C -0.6902(6) -1.0141(2) -0.52424(19) 0.0240(9) Uani 1 1 d . . .
C18 C -1.3343(5) -0.8488(2) -0.28341(15) 0.0157(7) Uani 1 1 d . . .
C8 C -0.8155(5) -0.9628(2) -0.55720(17) 0.0217(8) Uani 1 1 d . . .
C17 C -1.3997(5) -0.9180(2) -0.32365(16) 0.0167(7) Uani 1 1 d . . .
C14 C -1.2839(5) -0.8467(2) -0.45079(16) 0.0168(8) Uani 1 1 d . . .
H14 H -1.4096 -0.8552 -0.4730 0.020 Uiso 1 1 calc R . .
C23 C -1.1615(5) -0.8522(2) -0.24997(16) 0.0172(7) Uani 1 1 d . . .
H23 H -1.0817 -0.8978 -0.2526 0.021 Uiso 1 1 calc R . .
C19 C -1.4494(5) -0.7817(2) -0.27980(16) 0.0174(7) Uani 1 1 d . . .
C5 C -0.9310(5) -1.0132(2) -0.43430(18) 0.0219(8) Uani 1 1 d . . .
C10 C -0.7643(6) -0.9362(2) -0.61741(18) 0.0243(9) Uani 1 1 d . . .
H10 H -0.8497 -0.9030 -0.6405 0.029 Uiso 1 1 calc R . .
C16 C -1.1609(5) -0.7815(2) -0.47839(17) 0.0204(8) Uani 1 1 d . . .
H16A H -1.0192 -0.7881 -0.4766 0.024 Uiso 1 1 calc R . .
H16B H -1.2092 -0.7541 -0.5168 0.024 Uiso 1 1 calc R . .
C22 C -1.1072(5) -0.7880(2) -0.21269(16) 0.0205(8) Uani 1 1 d . . .
C15 C -1.2653(6) -0.7670(2) -0.41714(18) 0.0207(8) Uani 1 1 d . . .
H15A H -1.3780 -0.7311 -0.4179 0.025 Uiso 1 1 calc R . .
H15B H -1.1878 -0.7650 -0.3777 0.025 Uiso 1 1 calc R . .
C12 C -0.4656(6) -1.0079(3) -0.6112(2) 0.0326(10) Uani 1 1 d . . .
H12 H -0.3460 -1.0230 -0.6295 0.039 Uiso 1 1 calc R . .
C13 C -0.5165(6) -1.0358(2) -0.55104(19) 0.0292(10) Uani 1 1 d . . .
H13 H -0.4314 -1.0698 -0.5286 0.035 Uiso 1 1 calc R . .
C6 C -0.7499(6) -1.0463(2) -0.46285(18) 0.0240(8) Uani 1 1 d . . .
C2 C -1.2380(5) -0.9515(2) -0.36577(17) 0.0170(7) Uani 1 1 d . . .
C25 C -1.7460(6) -0.7071(2) -0.31139(19) 0.0254(9) Uani 1 1 d . . .
H25A H -1.6817 -0.6636 -0.3338 0.038 Uiso 1 1 calc R . .
H25B H -1.7662 -0.6922 -0.2669 0.038 Uiso 1 1 calc R . .
H25C H -1.8707 -0.7179 -0.3314 0.038 Uiso 1 1 calc R . .
C11 C -0.5885(6) -0.9583(2) -0.64403(19) 0.0301(9) Uani 1 1 d . . .
H11 H -0.5531 -0.9392 -0.6848 0.036 Uiso 1 1 calc R . .
Cl2 Cl -1.03211(16) -1.13868(7) -0.59923(5) 0.0393(3) Uani 1 1 d . . .
Cl3 Cl -1.1515(2) -1.20016(9) -0.47636(6) 0.0531(4) Uani 1 1 d . . .
C27 C -1.1558(8) -1.2159(3) -0.5590(2) 0.0431(12) Uani 1 1 d . . .
H27A H -1.2911 -1.2181 -0.5738 0.052 Uiso 1 1 calc R . .
H27B H -1.0942 -1.2673 -0.5689 0.052 Uiso 1 1 calc R . .


_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
Cl1 C22 1.744(4) . ?
F1 C26 1.331(4) . ?
F3 C26 1.341(4) . ?
O2 C24 1.362(4) . ?
O2 C17 1.431(4) . ?
O4 C1 1.378(5) . ?
O4 C5 1.345(4) . ?
O5 C6 1.226(5) . ?
O3 C1 1.195(4) . ?
N1 C24 1.358(5) . ?
N1 C19 1.420(5) . ?
N1 C25 1.470(4) . ?
O6 C9 1.214(4) . ?
C9 C4 1.499(5) . ?
C9 C8 1.496(5) . ?
F2 C26 1.330(4) . ?
C3 C4 1.463(5) . ?
C3 C14 1.493(5) . ?
C3 C2 1.376(5) . ?
C4 C5 1.339(5) . ?
C1 C2 1.479(5) . ?
C24 O1 1.209(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(6) . ?
C20 C19 1.391(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(5) . ?
C26 C17 1.577(5) . ?
C7 C8 1.411(5) . ?
C7 C13 1.380(6) . ?
C7 C6 1.463(6) . ?
C18 C17 1.514(5) . ?
C18 C23 1.391(5) . ?
C18 C19 1.388(5) . ?
C8 C10 1.392(5) . ?
C17 C2 1.538(5) . ?
C14 H14 1.0000 . ?
C14 C16 1.509(5) . ?
C14 C15 1.526(5) . ?
C23 H23 0.9500 . ?
C23 C22 1.391(5) . ?
C5 C6 1.500(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.500(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.397(6) . ?
C12 C11 1.381(6) . ?
C13 H13 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C11 H11 0.9500 . ?
Cl2 C27 1.777(5) . ?
Cl3 C27 1.761(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

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
C24 O2 C17 123.9(3) . . ?
C5 O4 C1 122.1(3) . . ?
C24 N1 C19 121.8(3) . . ?
C24 N1 C25 117.6(3) . . ?
C19 N1 C25 119.9(3) . . ?
O6 C9 C4 122.3(3) . . ?
O6 C9 C8 120.3(3) . . ?
C8 C9 C4 117.3(3) . . ?
C4 C3 C14 117.5(3) . . ?
C2 C3 C4 118.0(3) . . ?
C2 C3 C14 124.3(3) . . ?
C3 C4 C9 122.9(3) . . ?
C5 C4 C9 117.6(3) . . ?
C5 C4 C3 119.5(3) . . ?
O4 C1 C2 117.1(3) . . ?
O3 C1 O4 116.1(3) . . ?
O3 C1 C2 126.7(4) . . ?
N1 C24 O2 118.9(3) . . ?
O1 C24 O2 116.7(3) . . ?
O1 C24 N1 124.4(3) . . ?
C21 C20 H20 119.8 . . ?
C21 C20 C19 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
F1 C26 F3 105.9(3) . . ?
F1 C26 C17 114.8(3) . . ?
F3 C26 C17 107.9(3) . . ?
F2 C26 F1 109.3(3) . . ?
F2 C26 F3 107.2(3) . . ?
F2 C26 C17 111.5(3) . . ?
C8 C7 C6 119.3(3) . . ?
C13 C7 C8 120.0(4) . . ?
C13 C7 C6 120.7(4) . . ?
C23 C18 C17 120.6(3) . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 C23 120.1(3) . . ?
C7 C8 C9 121.3(3) . . ?
C10 C8 C9 119.3(3) . . ?
C10 C8 C7 119.3(4) . . ?
O2 C17 C26 101.3(3) . . ?
O2 C17 C18 112.5(3) . . ?
O2 C17 C2 104.9(3) . . ?
C18 C17 C26 108.1(3) . . ?
C18 C17 C2 112.9(3) . . ?
C2 C17 C26 116.6(3) . . ?
C3 C14 H14 114.7 . . ?
C3 C14 C16 121.0(3) . . ?
C3 C14 C15 121.5(3) . . ?
C16 C14 H14 114.7 . . ?
C16 C14 C15 59.2(2) . . ?
C15 C14 H14 114.7 . . ?
C18 C23 H23 120.4 . . ?
C22 C23 C18 119.1(3) . . ?
C22 C23 H23 120.4 . . ?
C20 C19 N1 120.5(3) . . ?
C18 C19 N1 119.7(3) . . ?
C18 C19 C20 119.8(3) . . ?
O4 C5 C6 112.4(3) . . ?
C4 C5 O4 122.7(3) . . ?
C4 C5 C6 124.7(3) . . ?
C8 C10 H10 119.8 . . ?
C8 C10 C11 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C14 C16 H16A 117.7 . . ?
C14 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C15 C16 C14 61.0(2) . . ?
C15 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
C21 C22 Cl1 120.6(3) . . ?
C21 C22 C23 121.2(3) . . ?
C23 C22 Cl1 118.3(3) . . ?
C14 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
C16 C15 C14 59.8(2) . . ?
C16 C15 H15A 117.8 . . ?
C16 C15 H15B 117.8 . . ?
H15A C15 H15B 114.9 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(4) . . ?
C7 C13 C12 120.1(4) . . ?
C7 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O5 C6 C7 123.6(4) . . ?
O5 C6 C5 119.4(4) . . ?
C7 C6 C5 116.9(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 C17 122.3(3) . . ?
C1 C2 C17 117.8(3) . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
Cl2 C27 H27A 109.5 . . ?
Cl2 C27 H27B 109.5 . . ?
Cl3 C27 Cl2 110.7(3) . . ?
Cl3 C27 H27A 109.5 . . ?
Cl3 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?

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
F1 C26 C17 O2 -162.6(3) . . . . ?
F1 C26 C17 C18 -44.2(4) . . . . ?
F1 C26 C17 C2 84.2(4) . . . . ?
F3 C26 C17 O2 -44.8(3) . . . . ?
F3 C26 C17 C18 73.6(4) . . . . ?
F3 C26 C17 C2 -158.0(3) . . . . ?
O2 C17 C2 C3 38.0(4) . . . . ?
O2 C17 C2 C1 -145.8(3) . . . . ?
O4 C1 C2 C3 2.1(5) . . . . ?
O4 C1 C2 C17 -174.2(3) . . . . ?
O4 C5 C6 O5 5.5(5) . . . . ?
O4 C5 C6 C7 -174.3(3) . . . . ?
O3 C1 C2 C3 178.9(4) . . . . ?
O3 C1 C2 C17 2.5(6) . . . . ?
O6 C9 C4 C3 -20.2(5) . . . . ?
O6 C9 C4 C5 157.3(4) . . . . ?
O6 C9 C8 C7 -164.2(3) . . . . ?
O6 C9 C8 C10 12.8(5) . . . . ?
C9 C4 C5 O4 -171.9(3) . . . . ?
C9 C4 C5 C6 13.3(5) . . . . ?
C9 C8 C10 C11 -179.1(3) . . . . ?
F2 C26 C17 O2 72.5(3) . . . . ?
F2 C26 C17 C18 -169.0(3) . . . . ?
F2 C26 C17 C2 -40.6(4) . . . . ?
C3 C4 C5 O4 5.6(5) . . . . ?
C3 C4 C5 C6 -169.2(3) . . . . ?
C3 C14 C16 C15 -110.6(4) . . . . ?
C3 C14 C15 C16 109.8(4) . . . . ?
C4 C9 C8 C7 12.9(5) . . . . ?
C4 C9 C8 C10 -170.0(3) . . . . ?
C4 C3 C14 C16 -45.0(5) . . . . ?
C4 C3 C14 C15 -115.7(4) . . . . ?
C4 C3 C2 C1 5.4(5) . . . . ?
C4 C3 C2 C17 -178.4(3) . . . . ?
C4 C5 C6 O5 -179.2(4) . . . . ?
C4 C5 C6 C7 1.0(5) . . . . ?
C1 O4 C5 C4 2.4(5) . . . . ?
C1 O4 C5 C6 177.9(3) . . . . ?
C24 O2 C17 C26 91.6(3) . . . . ?
C24 O2 C17 C18 -23.6(4) . . . . ?
C24 O2 C17 C2 -146.7(3) . . . . ?
C24 N1 C19 C20 170.0(3) . . . . ?
C24 N1 C19 C18 -9.3(5) . . . . ?
C20 C21 C22 Cl1 -178.0(3) . . . . ?
C20 C21 C22 C23 1.3(6) . . . . ?
C21 C20 C19 N1 -179.6(3) . . . . ?
C21 C20 C19 C18 -0.3(5) . . . . ?
C26 C17 C2 C3 149.0(3) . . . . ?
C26 C17 C2 C1 -34.7(4) . . . . ?
C7 C8 C10 C11 -2.0(5) . . . . ?
C18 C17 C2 C3 -84.9(4) . . . . ?
C18 C17 C2 C1 91.3(4) . . . . ?
C18 C23 C22 Cl1 177.9(3) . . . . ?
C18 C23 C22 C21 -1.3(5) . . . . ?
C8 C9 C4 C3 162.7(3) . . . . ?
C8 C9 C4 C5 -19.8(5) . . . . ?
C8 C7 C13 C12 -0.9(6) . . . . ?
C8 C7 C6 O5 171.7(4) . . . . ?
C8 C7 C6 C5 -8.5(5) . . . . ?
C8 C10 C11 C12 1.2(6) . . . . ?
C17 O2 C24 N1 15.1(5) . . . . ?
C17 O2 C24 O1 -166.0(3) . . . . ?
C17 C18 C23 C22 -179.0(3) . . . . ?
C17 C18 C19 N1 -0.8(5) . . . . ?
C17 C18 C19 C20 179.8(3) . . . . ?
C14 C3 C4 C9 -16.2(5) . . . . ?
C14 C3 C4 C5 166.4(3) . . . . ?
C14 C3 C2 C1 -170.1(3) . . . . ?
C14 C3 C2 C17 6.1(5) . . . . ?
C23 C18 C17 O2 -164.7(3) . . . . ?
C23 C18 C17 C26 84.3(4) . . . . ?
C23 C18 C17 C2 -46.1(4) . . . . ?
C23 C18 C19 N1 179.6(3) . . . . ?
C23 C18 C19 C20 0.3(5) . . . . ?
C19 N1 C24 O2 2.7(5) . . . . ?
C19 N1 C24 O1 -176.1(3) . . . . ?
C19 C20 C21 C22 -0.5(6) . . . . ?
C19 C18 C17 O2 15.7(4) . . . . ?
C19 C18 C17 C26 -95.3(4) . . . . ?
C19 C18 C17 C2 134.3(3) . . . . ?
C19 C18 C23 C22 0.5(5) . . . . ?
C5 O4 C1 O3 176.6(3) . . . . ?
C5 O4 C1 C2 -6.3(5) . . . . ?
C13 C7 C8 C9 178.8(3) . . . . ?
C13 C7 C8 C10 1.8(5) . . . . ?
C13 C7 C6 O5 -5.9(6) . . . . ?
C13 C7 C6 C5 173.9(3) . . . . ?
C13 C12 C11 C10 -0.3(6) . . . . ?
C6 C7 C8 C9 1.2(5) . . . . ?
C6 C7 C8 C10 -175.8(4) . . . . ?
C6 C7 C13 C12 176.7(4) . . . . ?
C2 C3 C4 C9 168.0(3) . . . . ?
C2 C3 C4 C5 -9.4(5) . . . . ?
C2 C3 C14 C16 130.5(4) . . . . ?
C2 C3 C14 C15 59.8(5) . . . . ?
C25 N1 C24 O2 172.8(3) . . . . ?
C25 N1 C24 O1 -6.0(5) . . . . ?
C25 N1 C19 C20 0.1(5) . . . . ?
C25 N1 C19 C18 -179.2(3) . . . . ?
C11 C12 C13 C7 0.1(6) . . . . ?

####################################################################### 
# 
# 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_c510
_database_code_depnum_ccdc_archive 'CCDC 1909885'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Peking Union Medical College
China
;
_audit_update_record             
;
2019-04-13 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H12 Cl2 O3'
_chemical_formula_weight         419.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2581(15)
_cell_length_b                   14.444(3)
_cell_length_c                   17.808(4)
_cell_angle_alpha                75.829(4)
_cell_angle_beta                 84.143(4)
_cell_angle_gamma                87.362(5)
_cell_volume                     1800.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    914
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.28

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6173
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23747
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8254
_reflns_number_gt                7291
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0569P)²+0.9183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8254
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.62566(7) 0.93478(3) 0.06816(3) 0.02349(12) Uani 1 1 d . . .
Cl2 Cl 1.06396(7) 0.30821(4) 0.03769(3) 0.02379(12) Uani 1 1 d . . .
Cl3 Cl 0.11231(7) -0.17290(4) 0.06564(3) 0.02672(13) Uani 1 1 d . . .
Cl4 Cl 0.59381(7) 0.38539(4) -0.00294(3) 0.02389(12) Uani 1 1 d . . .
O1 O 0.72259(18) 0.58128(9) 0.38331(7) 0.0143(3) Uani 1 1 d . . .
O2 O 1.0151(2) 0.29013(9) 0.38919(8) 0.0199(3) Uani 1 1 d . . .
O3 O 0.9845(2) 0.24734(10) 0.54636(9) 0.0277(3) Uani 1 1 d . . .
O4 O 0.22342(18) -0.01642(9) 0.38238(7) 0.0145(3) Uani 1 1 d . . .
O5 O 0.49408(19) 0.26722(9) 0.38107(8) 0.0191(3) Uani 1 1 d . . .
O6 O 0.4662(2) 0.22141(10) 0.53835(8) 0.0245(3) Uani 1 1 d . . .
C1 C 0.9292(3) 0.34561(13) 0.42168(11) 0.0156(4) Uani 1 1 d . . .
C2 C 0.9184(3) 0.32247(13) 0.51265(11) 0.0174(4) Uani 1 1 d . . .
C3 C 0.8303(3) 0.39317(13) 0.55420(11) 0.0157(4) Uani 1 1 d . . .
C4 C 0.8216(3) 0.37293(13) 0.63472(11) 0.0173(4) Uani 1 1 d . . .
H4 H 0.8712 0.3141 0.6628 0.021 Uiso 1 1 calc R . .
C5 C 0.7405(3) 0.43838(14) 0.67457(11) 0.0182(4) Uani 1 1 d . . .
H5 H 0.7343 0.4242 0.7297 0.022 Uiso 1 1 calc R . .
C6 C 0.6685(3) 0.52452(13) 0.63334(11) 0.0173(4) Uani 1 1 d . . .
H6 H 0.6122 0.5689 0.6607 0.021 Uiso 1 1 calc R . .
C7 C 0.6778(3) 0.54671(13) 0.55247(11) 0.0155(4) Uani 1 1 d . . .
H7 H 0.6296 0.6061 0.5247 0.019 Uiso 1 1 calc R . .
C8 C 0.7584(2) 0.48113(13) 0.51271(11) 0.0143(4) Uani 1 1 d . . .
C9 C 0.7744(2) 0.49687(13) 0.42887(11) 0.0142(4) Uani 1 1 d . . .
C10 C 0.8413(2) 0.43541(13) 0.38459(11) 0.0149(4) Uani 1 1 d . . .
C11 C 0.8279(2) 0.48535(13) 0.30443(11) 0.0142(4) Uani 1 1 d . . .
C12 C 0.7553(3) 0.57354(13) 0.30673(10) 0.0151(4) Uani 1 1 d . . .
C13 C 0.7150(2) 0.66117(13) 0.24867(11) 0.0151(4) Uani 1 1 d . . .
C14 C 0.7408(3) 0.74970(13) 0.26448(11) 0.0164(4) Uani 1 1 d . . .
H14 H 0.7770 0.7522 0.3137 0.020 Uiso 1 1 calc R . .
C15 C 0.7137(3) 0.83363(13) 0.20891(11) 0.0170(4) Uani 1 1 d . . .
H15 H 0.7334 0.8936 0.2194 0.020 Uiso 1 1 calc R . .
C16 C 0.6576(3) 0.82918(13) 0.13778(11) 0.0169(4) Uani 1 1 d . . .
C17 C 0.6268(3) 0.74274(14) 0.12133(11) 0.0183(4) Uani 1 1 d . . .
H17 H 0.5865 0.7409 0.0726 0.022 Uiso 1 1 calc R . .
C18 C 0.6555(3) 0.65884(14) 0.17679(11) 0.0173(4) Uani 1 1 d . . .
H18 H 0.6347 0.5992 0.1659 0.021 Uiso 1 1 calc R . .
C19 C 0.8827(2) 0.44550(13) 0.23627(11) 0.0144(4) Uani 1 1 d . . .
C20 C 0.9810(3) 0.49748(13) 0.16849(11) 0.0167(4) Uani 1 1 d . . .
H20 H 1.0124 0.5617 0.1648 0.020 Uiso 1 1 calc R . .
C21 C 1.0329(3) 0.45630(14) 0.10664(11) 0.0173(4) Uani 1 1 d . . .
H21 H 1.0976 0.4922 0.0604 0.021 Uiso 1 1 calc R . .
C22 C 0.9891(3) 0.36227(14) 0.11325(11) 0.0174(4) Uani 1 1 d . . .
C23 C 0.8909(3) 0.30934(14) 0.17908(11) 0.0177(4) Uani 1 1 d . . .
H23 H 0.8610 0.2450 0.1825 0.021 Uiso 1 1 calc R . .
C24 C 0.8367(3) 0.35135(13) 0.24005(11) 0.0163(4) Uani 1 1 d . . .
H24 H 0.7672 0.3157 0.2851 0.020 Uiso 1 1 calc R . .
C25 C 0.4177(2) 0.19397(13) 0.41506(11) 0.0146(4) Uani 1 1 d . . .
C26 C 0.4037(3) 0.16673(13) 0.50614(11) 0.0164(4) Uani 1 1 d . . .
C27 C 0.3188(3) 0.07481(13) 0.54951(11) 0.0151(4) Uani 1 1 d . . .
C28 C 0.3055(3) 0.05063(14) 0.63036(11) 0.0167(4) Uani 1 1 d . . .
H28 H 0.3500 0.0928 0.6575 0.020 Uiso 1 1 calc R . .
C29 C 0.2270(3) -0.03516(14) 0.67152(11) 0.0175(4) Uani 1 1 d . . .
H29 H 0.2172 -0.0514 0.7268 0.021 Uiso 1 1 calc R . .
C30 C 0.1629(3) -0.09737(13) 0.63182(11) 0.0171(4) Uani 1 1 d . . .
H30 H 0.1090 -0.1558 0.6603 0.020 Uiso 1 1 calc R . .
C31 C 0.1769(2) -0.07476(13) 0.55090(11) 0.0151(4) Uani 1 1 d . . .
H31 H 0.1341 -0.1177 0.5240 0.018 Uiso 1 1 calc R . .
C32 C 0.2543(2) 0.01156(13) 0.50971(11) 0.0136(3) Uani 1 1 d . . .
C33 C 0.2738(2) 0.04154(13) 0.42565(11) 0.0139(3) Uani 1 1 d . . .
C34 C 0.3418(2) 0.12508(13) 0.37940(11) 0.0141(4) Uani 1 1 d . . .
C35 C 0.3345(3) 0.11899(13) 0.30011(11) 0.0147(4) Uani 1 1 d . . .
C36 C 0.2589(2) 0.03260(13) 0.30528(10) 0.0143(4) Uani 1 1 d . . .
C37 C 0.2130(2) -0.01797(13) 0.24807(11) 0.0150(4) Uani 1 1 d . . .
C38 C 0.1426(3) 0.03180(14) 0.17865(11) 0.0173(4) Uani 1 1 d . . .
H38 H 0.1173 0.0985 0.1700 0.021 Uiso 1 1 calc R . .
C39 C 0.1094(3) -0.01551(15) 0.12247(11) 0.0196(4) Uani 1 1 d . . .
H39 H 0.0617 0.0182 0.0754 0.024 Uiso 1 1 calc R . .
C40 C 0.1472(3) -0.11267(15) 0.13619(11) 0.0188(4) Uani 1 1 d . . .
C41 C 0.2123(3) -0.16369(14) 0.20493(11) 0.0192(4) Uani 1 1 d . . .
H41 H 0.2353 -0.2306 0.2135 0.023 Uiso 1 1 calc R . .
C42 C 0.2437(3) -0.11660(14) 0.26123(11) 0.0173(4) Uani 1 1 d . . .
H42 H 0.2863 -0.1515 0.3090 0.021 Uiso 1 1 calc R . .
C43 C 0.4036(3) 0.18661(13) 0.22705(11) 0.0148(4) Uani 1 1 d . . .
C44 C 0.3732(3) 0.28505(13) 0.21522(11) 0.0166(4) Uani 1 1 d . . .
H44 H 0.3101 0.3102 0.2555 0.020 Uiso 1 1 calc R . .
C45 C 0.4345(3) 0.34632(13) 0.14516(11) 0.0175(4) Uani 1 1 d . . .
H45 H 0.4159 0.4134 0.1376 0.021 Uiso 1 1 calc R . .
C46 C 0.5228(3) 0.30883(14) 0.08632(11) 0.0177(4) Uani 1 1 d . . .
C47 C 0.5570(3) 0.21174(14) 0.09632(11) 0.0176(4) Uani 1 1 d . . .
H47 H 0.6188 0.1870 0.0555 0.021 Uiso 1 1 calc R . .
C48 C 0.4990(3) 0.15152(13) 0.16712(11) 0.0163(4) Uani 1 1 d . . .
H48 H 0.5245 0.0849 0.1752 0.020 Uiso 1 1 calc R . .


_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
Cl1 C16 1.7371(19) . ?
Cl2 C22 1.7442(19) . ?
Cl3 C40 1.7378(19) . ?
Cl4 C46 1.7435(19) . ?
O1 C9 1.350(2) . ?
O1 C12 1.391(2) . ?
O2 C1 1.214(2) . ?
O3 C2 1.208(2) . ?
O4 C33 1.353(2) . ?
O4 C36 1.386(2) . ?
O5 C25 1.210(2) . ?
O6 C26 1.211(2) . ?
C1 C10 1.455(3) . ?
C1 C2 1.566(3) . ?
C2 C3 1.487(3) . ?
C3 C4 1.387(3) . ?
C3 C8 1.411(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.448(3) . ?
C9 C10 1.368(3) . ?
C10 C11 1.444(3) . ?
C11 C12 1.364(3) . ?
C11 C19 1.478(3) . ?
C12 C13 1.464(3) . ?
C13 C14 1.399(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.386(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.386(3) . ?
C19 C24 1.399(3) . ?
C19 C20 1.400(3) . ?
C20 C21 1.387(3) . ?
C21 C22 1.383(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.384(3) . ?
C25 C34 1.459(3) . ?
C25 C26 1.566(3) . ?
C26 C27 1.488(3) . ?
C27 C28 1.390(3) . ?
C27 C32 1.407(3) . ?
C28 C29 1.390(3) . ?
C29 C30 1.393(3) . ?
C30 C31 1.392(3) . ?
C31 C32 1.393(3) . ?
C32 C33 1.447(3) . ?
C33 C34 1.365(3) . ?
C34 C35 1.443(2) . ?
C35 C36 1.365(3) . ?
C35 C43 1.479(3) . ?
C36 C37 1.462(3) . ?
C37 C42 1.397(3) . ?
C37 C38 1.402(3) . ?
C38 C39 1.387(3) . ?
C39 C40 1.384(3) . ?
C40 C41 1.382(3) . ?
C41 C42 1.384(3) . ?
C43 C44 1.396(3) . ?
C43 C48 1.399(3) . ?
C44 C45 1.386(3) . ?
C45 C46 1.382(3) . ?
C46 C47 1.384(3) . ?
C47 C48 1.383(3) . ?

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
C9 O1 C12 106.84(14) . . ?
C33 O4 C36 106.36(14) . . ?
O2 C1 C10 126.61(18) . . ?
O2 C1 C2 117.85(16) . . ?
C10 C1 C2 115.47(16) . . ?
O3 C2 C3 122.50(18) . . ?
O3 C2 C1 118.01(17) . . ?
C3 C2 C1 119.49(16) . . ?
C4 C3 C8 119.62(17) . . ?
C4 C3 C2 119.50(17) . . ?
C8 C3 C2 120.86(17) . . ?
C3 C4 C5 120.32(17) . . ?
C6 C5 C4 119.73(18) . . ?
C5 C6 C7 120.87(18) . . ?
C8 C7 C6 119.36(17) . . ?
C7 C8 C3 120.10(17) . . ?
C7 C8 C9 123.82(17) . . ?
C3 C8 C9 116.08(16) . . ?
O1 C9 C10 110.66(16) . . ?
O1 C9 C8 120.93(16) . . ?
C10 C9 C8 128.40(17) . . ?
C9 C10 C11 106.67(16) . . ?
C9 C10 C1 119.30(17) . . ?
C11 C10 C1 133.39(17) . . ?
C12 C11 C10 105.51(16) . . ?
C12 C11 C19 129.13(17) . . ?
C10 C11 C19 125.37(16) . . ?
C11 C12 O1 110.32(16) . . ?
C11 C12 C13 135.34(17) . . ?
O1 C12 C13 114.23(15) . . ?
C14 C13 C18 118.98(17) . . ?
C14 C13 C12 119.28(16) . . ?
C18 C13 C12 121.72(17) . . ?
C15 C14 C13 120.49(17) . . ?
C14 C15 C16 119.30(18) . . ?
C17 C16 C15 121.41(17) . . ?
C17 C16 Cl1 119.60(15) . . ?
C15 C16 Cl1 118.99(15) . . ?
C16 C17 C18 119.16(18) . . ?
C17 C18 C13 120.63(18) . . ?
C24 C19 C20 118.56(17) . . ?
C24 C19 C11 118.62(16) . . ?
C20 C19 C11 122.81(16) . . ?
C21 C20 C19 120.72(17) . . ?
C22 C21 C20 119.09(18) . . ?
C23 C22 C21 121.57(17) . . ?
C23 C22 Cl2 119.07(15) . . ?
C21 C22 Cl2 119.34(15) . . ?
C22 C23 C24 119.05(18) . . ?
C23 C24 C19 120.97(18) . . ?
O5 C25 C34 126.28(17) . . ?
O5 C25 C26 118.09(16) . . ?
C34 C25 C26 115.58(16) . . ?
O6 C26 C27 122.66(17) . . ?
O6 C26 C25 117.96(17) . . ?
C27 C26 C25 119.37(16) . . ?
C28 C27 C32 119.65(17) . . ?
C28 C27 C26 119.50(17) . . ?
C32 C27 C26 120.85(16) . . ?
C29 C28 C27 120.05(18) . . ?
C28 C29 C30 120.05(18) . . ?
C31 C30 C29 120.66(18) . . ?
C30 C31 C32 119.23(18) . . ?
C31 C32 C27 120.35(17) . . ?
C31 C32 C33 123.26(17) . . ?
C27 C32 C33 116.39(16) . . ?
O4 C33 C34 111.01(16) . . ?
O4 C33 C32 120.60(16) . . ?
C34 C33 C32 128.38(17) . . ?
C33 C34 C35 106.52(16) . . ?
C33 C34 C25 119.33(17) . . ?
C35 C34 C25 133.87(17) . . ?
C36 C35 C34 105.37(16) . . ?
C36 C35 C43 125.42(17) . . ?
C34 C35 C43 129.10(17) . . ?
C35 C36 O4 110.71(16) . . ?
C35 C36 C37 134.00(17) . . ?
O4 C36 C37 115.28(15) . . ?
C42 C37 C38 119.16(17) . . ?
C42 C37 C36 120.09(17) . . ?
C38 C37 C36 120.72(17) . . ?
C39 C38 C37 120.60(18) . . ?
C40 C39 C38 118.78(18) . . ?
C41 C40 C39 121.69(17) . . ?
C41 C40 Cl3 118.71(16) . . ?
C39 C40 Cl3 119.60(16) . . ?
C40 C41 C42 119.48(18) . . ?
C41 C42 C37 120.24(18) . . ?
C44 C43 C48 118.58(17) . . ?
C44 C43 C35 121.88(17) . . ?
C48 C43 C35 119.54(16) . . ?
C45 C44 C43 120.50(18) . . ?
C46 C45 C44 119.30(18) . . ?
C45 C46 C47 121.71(18) . . ?
C45 C46 Cl4 119.44(15) . . ?
C47 C46 Cl4 118.85(15) . . ?
C48 C47 C46 118.43(18) . . ?
C47 C48 C43 121.42(17) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_5707
_database_code_depnum_ccdc_archive 'CCDC 1909886'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Peking Union Medical College
China
;
_audit_update_record             
;
2019-04-13 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H12 O3'
_chemical_formula_sum            'C19 H12 O3'
_chemical_formula_weight         288.29
_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 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.3669(16)
_cell_length_b                   6.5367(3)
_cell_length_c                   16.8120(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.656(12)
_cell_angle_gamma                90.00
_cell_volume                     1355.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1547
_cell_measurement_temperature    107.70(10)
_cell_measurement_theta_max      27.9370
_cell_measurement_theta_min      3.9730
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82175
_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    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5832
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.30
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107.70(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8588
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -99.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega  -27.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335    0.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335    0.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000 -150.0000 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0363667000
_diffrn_orient_matrix_UB_12      -0.0781446000
_diffrn_orient_matrix_UB_13      0.0233024000
_diffrn_orient_matrix_UB_21      0.0394717000
_diffrn_orient_matrix_UB_22      0.0750739000
_diffrn_orient_matrix_UB_23      0.0215509000
_diffrn_orient_matrix_UB_31      -0.0206717000
_diffrn_orient_matrix_UB_32      0.0062192000
_diffrn_orient_matrix_UB_33      0.0329947000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2111
_reflns_number_total             2657
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.258
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0426P)²+0.6376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1141
_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
O1 O 0.33830(9) 0.28622(19) 0.42275(7) 0.0173(3) Uani 1 1 d . . .
O3 O 0.66984(10) 0.3285(2) 0.31811(8) 0.0278(3) Uani 1 1 d . . .
O2 O 0.46066(10) 0.3423(2) 0.20198(8) 0.0278(3) Uani 1 1 d . . .
C4 C 0.42608(14) 0.2853(3) 0.40172(11) 0.0168(4) Uani 1 1 d . . .
C5 C 0.53445(14) 0.2613(3) 0.46687(11) 0.0159(4) Uani 1 1 d . . .
C8 C 0.47739(14) 0.3195(3) 0.27793(11) 0.0192(4) Uani 1 1 d . . .
C10 C 0.74730(15) 0.2149(3) 0.58357(12) 0.0218(4) Uani 1 1 d . . .
H10 H 0.8184 0.1987 0.6227 0.026 Uiso 1 1 calc R . .
C6 C 0.62009(14) 0.2708(3) 0.43757(11) 0.0180(4) Uani 1 1 d . . .
C11 C 0.66252(15) 0.2062(3) 0.61179(12) 0.0202(4) Uani 1 1 d . . .
H11 H 0.6771 0.1843 0.6699 0.024 Uiso 1 1 calc R . .
C3 C 0.39575(14) 0.3080(3) 0.31454(11) 0.0174(4) Uani 1 1 d . . .
C12 C 0.55611(15) 0.2301(3) 0.55389(11) 0.0186(4) Uani 1 1 d . . .
H12 H 0.4996 0.2253 0.5731 0.022 Uiso 1 1 calc R . .
C1 C 0.24779(14) 0.3115(3) 0.34568(11) 0.0178(4) Uani 1 1 d . . .
C18 C -0.04453(14) 0.4178(3) 0.30677(12) 0.0224(4) Uani 1 1 d . . .
H18 H -0.1057 0.4738 0.2642 0.027 Uiso 1 1 calc R . .
C14 C 0.14456(14) 0.3221(3) 0.35724(11) 0.0180(4) Uani 1 1 d . . .
C7 C 0.59760(14) 0.3066(3) 0.34459(12) 0.0199(4) Uani 1 1 d . . .
C9 C 0.72614(15) 0.2475(3) 0.49711(12) 0.0217(4) Uani 1 1 d . . .
H9 H 0.7833 0.2540 0.4787 0.026 Uiso 1 1 calc R . .
C17 C -0.05061(15) 0.3457(3) 0.38210(12) 0.0242(4) Uani 1 1 d . . .
H17 H -0.1157 0.3524 0.3900 0.029 Uiso 1 1 calc R . .
C19 C 0.05206(14) 0.4074(3) 0.29408(12) 0.0208(4) Uani 1 1 d . . .
H19 H 0.0552 0.4575 0.2433 0.025 Uiso 1 1 calc R . .
C2 C 0.27933(14) 0.3236(3) 0.27752(11) 0.0184(4) Uani 1 1 d . . .
C16 C 0.04115(15) 0.2631(3) 0.44593(13) 0.0263(5) Uani 1 1 d . . .
H16 H 0.0376 0.2157 0.4969 0.032 Uiso 1 1 calc R . .
C13 C 0.21248(15) 0.3463(3) 0.18283(11) 0.0234(4) Uani 1 1 d . . .
H13A H 0.2114 0.4873 0.1666 0.035 Uiso 1 1 calc R . .
H13B H 0.1398 0.3010 0.1708 0.035 Uiso 1 1 calc R . .
H13C H 0.2435 0.2649 0.1506 0.035 Uiso 1 1 calc R . .
C15 C 0.13809(15) 0.2511(3) 0.43375(12) 0.0216(4) Uani 1 1 d . . .
H15 H 0.1991 0.1956 0.4767 0.026 Uiso 1 1 calc R . .


_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 C4 1.350(2) . ?
O1 C1 1.401(2) . ?
O3 C7 1.218(2) . ?
O2 C8 1.218(2) . ?
C4 C5 1.449(2) . ?
C4 C3 1.370(2) . ?
C5 C6 1.411(2) . ?
C5 C12 1.393(2) . ?
C8 C3 1.447(2) . ?
C8 C7 1.568(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C10 C9 1.386(3) . ?
C6 C7 1.492(2) . ?
C6 C9 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(3) . ?
C3 C2 1.440(2) . ?
C12 H12 0.9300 . ?
C1 C14 1.467(2) . ?
C1 C2 1.367(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.383(3) . ?
C18 C19 1.389(2) . ?
C14 C19 1.399(2) . ?
C14 C15 1.401(3) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.390(3) . ?
C19 H19 0.9300 . ?
C2 C13 1.503(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.390(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15 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
C4 O1 C1 106.65(13) . . ?
O1 C4 C5 121.28(15) . . ?
O1 C4 C3 110.55(15) . . ?
C3 C4 C5 128.17(16) . . ?
C6 C5 C4 116.13(16) . . ?
C12 C5 C4 123.55(16) . . ?
C12 C5 C6 120.33(16) . . ?
O2 C8 C3 126.06(17) . . ?
O2 C8 C7 118.67(15) . . ?
C3 C8 C7 115.24(15) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.07(17) . . ?
C5 C6 C7 120.63(16) . . ?
C9 C6 C5 118.81(16) . . ?
C9 C6 C7 120.56(16) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.43(17) . . ?
C12 C11 H11 119.8 . . ?
C4 C3 C8 120.00(16) . . ?
C4 C3 C2 107.17(15) . . ?
C2 C3 C8 132.78(16) . . ?
C5 C12 H12 120.2 . . ?
C11 C12 C5 119.68(17) . . ?
C11 C12 H12 120.2 . . ?
O1 C1 C14 113.84(15) . . ?
C2 C1 O1 110.30(15) . . ?
C2 C1 C14 135.85(17) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.67(17) . . ?
C19 C18 H18 119.7 . . ?
C19 C14 C1 121.31(16) . . ?
C19 C14 C15 118.68(16) . . ?
C15 C14 C1 119.98(16) . . ?
O3 C7 C8 118.11(16) . . ?
O3 C7 C6 122.23(17) . . ?
C6 C7 C8 119.65(14) . . ?
C10 C9 C6 120.68(17) . . ?
C10 C9 H9 119.7 . . ?
C6 C9 H9 119.7 . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C16 119.57(17) . . ?
C16 C17 H17 120.2 . . ?
C18 C19 C14 120.34(17) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C3 C2 C13 124.57(16) . . ?
C1 C2 C3 105.33(15) . . ?
C1 C2 C13 130.10(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.23(18) . . ?
C15 C16 H16 119.9 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.49(18) . . ?
C16 C15 H15 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 C4 C5 C6 -177.57(15) . . . . ?
O1 C4 C5 C12 2.5(3) . . . . ?
O1 C4 C3 C8 177.53(15) . . . . ?
O1 C4 C3 C2 -0.3(2) . . . . ?
O1 C1 C14 C19 160.17(16) . . . . ?
O1 C1 C14 C15 -18.0(2) . . . . ?
O1 C1 C2 C3 -0.8(2) . . . . ?
O1 C1 C2 C13 178.59(18) . . . . ?
O2 C8 C3 C4 -178.93(18) . . . . ?
O2 C8 C3 C2 -1.8(3) . . . . ?
O2 C8 C7 O3 3.0(3) . . . . ?
O2 C8 C7 C6 -177.73(17) . . . . ?
C4 O1 C1 C14 -178.27(14) . . . . ?
C4 O1 C1 C2 0.69(19) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C4 C5 C6 C9 -179.59(16) . . . . ?
C4 C5 C12 C11 179.23(16) . . . . ?
C4 C3 C2 C1 0.7(2) . . . . ?
C4 C3 C2 C13 -178.79(17) . . . . ?
C5 C4 C3 C8 -2.8(3) . . . . ?
C5 C4 C3 C2 179.34(17) . . . . ?
C5 C6 C7 O3 175.25(18) . . . . ?
C5 C6 C7 C8 -4.0(3) . . . . ?
C5 C6 C9 C10 0.2(3) . . . . ?
C8 C3 C2 C1 -176.74(19) . . . . ?
C8 C3 C2 C13 3.8(3) . . . . ?
C10 C11 C12 C5 0.5(3) . . . . ?
C6 C5 C12 C11 -0.7(3) . . . . ?
C11 C10 C9 C6 -0.4(3) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C3 C4 C5 C12 -177.05(18) . . . . ?
C3 C8 C7 O3 -175.40(17) . . . . ?
C3 C8 C7 C6 3.9(2) . . . . ?
C12 C5 C6 C7 -179.31(16) . . . . ?
C12 C5 C6 C9 0.3(3) . . . . ?
C1 O1 C4 C5 -179.88(15) . . . . ?
C1 O1 C4 C3 -0.23(19) . . . . ?
C1 C14 C19 C18 -179.33(17) . . . . ?
C1 C14 C15 C16 179.07(17) . . . . ?
C18 C17 C16 C15 -0.7(3) . . . . ?
C14 C1 C2 C3 177.8(2) . . . . ?
C14 C1 C2 C13 -2.8(4) . . . . ?
C7 C8 C3 C4 -0.7(2) . . . . ?
C7 C8 C3 C2 176.50(18) . . . . ?
C7 C6 C9 C10 179.84(17) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C6 C7 O3 -4.4(3) . . . . ?
C9 C6 C7 C8 176.42(17) . . . . ?
C17 C18 C19 C14 0.5(3) . . . . ?
C17 C16 C15 C14 0.0(3) . . . . ?
C19 C18 C17 C16 0.4(3) . . . . ?
C19 C14 C15 C16 0.9(3) . . . . ?
C2 C1 C14 C19 -18.4(3) . . . . ?
C2 C1 C14 C15 163.4(2) . . . . ?
C15 C14 C19 C18 -1.1(3) . . . . ?

