# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_xb1241_0m
_database_code_depnum_ccdc_archive 'CCDC 1996332'
loop_
_audit_author_name
_audit_author_address
zhuhaitao-a
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2020-04-11 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H20 O'
_chemical_formula_weight         396.46

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.580(7)
_cell_length_b                   9.356(3)
_cell_length_c                   20.482(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.071(4)
_cell_angle_gamma                90.00
_cell_volume                     4168.9(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    487
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      16.96

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            10313
_diffrn_reflns_av_R_equivalents  0.1252
_diffrn_reflns_av_sigmaI/netI    0.1650
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3703
_reflns_number_gt                1437
_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)+(0.0958P)²+0.0408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2094
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2496
_refine_ls_wR_factor_gt          0.1780
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.002
_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 0.22328(19) 0.6228(4) 0.3218(2) 0.0651(12) Uani 1 1 d . . .
C1 C 0.1761(3) 0.5538(6) 0.2989(3) 0.0502(15) Uani 1 1 d . . .
C2 C 0.1551(3) 0.4285(6) 0.2442(3) 0.0494(15) Uani 1 1 d . . .
C3 C 0.1794(3) 0.3678(6) 0.2066(3) 0.0518(15) Uani 1 1 d . . .
H3 H 0.2157 0.4025 0.2154 0.062 Uiso 1 1 calc R . .
C4 C 0.1489(3) 0.2551(6) 0.1557(3) 0.0615(18) Uani 1 1 d . . .
H4 H 0.1651 0.2128 0.1305 0.074 Uiso 1 1 calc R . .
C5 C 0.0960(3) 0.2040(6) 0.1414(3) 0.0600(17) Uani 1 1 d . . .
H5 H 0.0751 0.1315 0.1041 0.072 Uiso 1 1 calc R . .
C6 C 0.0719(3) 0.2588(6) 0.1823(3) 0.0569(16) Uani 1 1 d . . .
H6 H 0.0365 0.2206 0.1743 0.068 Uiso 1 1 calc R . .
C7 C 0.1026(2) 0.3712(6) 0.2347(3) 0.0439(14) Uani 1 1 d . . .
C8 C 0.0868(2) 0.4479(5) 0.2840(3) 0.0434(14) Uani 1 1 d . . .
H8 H 0.0439 0.4796 0.2512 0.052 Uiso 1 1 calc R . .
C9 C 0.1302(2) 0.5756(6) 0.3159(3) 0.0419(13) Uani 1 1 d . . .
C10 C 0.1242(2) 0.6835(6) 0.3555(3) 0.0476(14) Uani 1 1 d . . .
C11 C 0.0779(2) 0.6783(6) 0.3728(3) 0.0437(13) Uani 1 1 d . . .
C12 C 0.0462(3) 0.8058(6) 0.3651(3) 0.0577(16) Uani 1 1 d . . .
H12 H 0.0544 0.8881 0.3473 0.069 Uiso 1 1 calc R . .
C13 C 0.0037(3) 0.8126(7) 0.3829(4) 0.0637(18) Uani 1 1 d . . .
H13 H -0.0177 0.8969 0.3750 0.076 Uiso 1 1 calc R . .
C14 C -0.0071(3) 0.6935(7) 0.4127(4) 0.0678(19) Uani 1 1 d . . .
H14 H -0.0350 0.6978 0.4262 0.081 Uiso 1 1 calc R . .
C15 C 0.0234(3) 0.5683(6) 0.4224(3) 0.0525(15) Uani 1 1 d . . .
H15 H 0.0161 0.4896 0.4435 0.063 Uiso 1 1 calc R . .
C16 C 0.0644(2) 0.5546(6) 0.4022(3) 0.0475(14) Uani 1 1 d . . .
C17 C 0.0917(2) 0.4120(5) 0.4083(3) 0.0440(14) Uani 1 1 d . . .
C18 C 0.1000(2) 0.3628(6) 0.3552(3) 0.0427(13) Uani 1 1 d . . .
H18 H 0.1148 0.2701 0.3616 0.051 Uiso 1 1 calc R . .
C19 C 0.1081(2) 0.3188(6) 0.4787(3) 0.0440(14) Uani 1 1 d . . .
C20 C 0.1397(2) 0.3739(6) 0.5546(3) 0.0507(15) Uani 1 1 d . . .
H20 H 0.1465 0.4718 0.5624 0.061 Uiso 1 1 calc R . .
C21 C 0.1614(3) 0.2852(7) 0.6195(3) 0.0587(17) Uani 1 1 d . . .
H21 H 0.1833 0.3233 0.6708 0.070 Uiso 1 1 calc R . .
C22 C 0.1507(3) 0.1405(7) 0.6083(4) 0.0650(17) Uani 1 1 d . . .
H22 H 0.1652 0.0810 0.6521 0.078 Uiso 1 1 calc R . .
C23 C 0.1189(3) 0.0834(6) 0.5332(3) 0.0596(17) Uani 1 1 d . . .
H23 H 0.1122 -0.0146 0.5256 0.071 Uiso 1 1 calc R . .
C24 C 0.0973(3) 0.1726(6) 0.4697(3) 0.0532(15) Uani 1 1 d . . .
H24 H 0.0745 0.1341 0.4185 0.064 Uiso 1 1 calc R . .
C25 C 0.1613(2) 0.8192(6) 0.3785(3) 0.0504(15) Uani 1 1 d . . .
C26 C 0.1912(3) 0.8693(6) 0.4574(3) 0.0539(15) Uani 1 1 d . . .
H26 H 0.1894 0.8173 0.4947 0.065 Uiso 1 1 calc R . .
C27 C 0.2234(3) 0.9980(6) 0.4787(4) 0.0635(18) Uani 1 1 d . . .
H27 H 0.2434 1.0320 0.5306 0.076 Uiso 1 1 calc R . .
C28 C 0.2258(3) 1.0764(7) 0.4223(4) 0.0640(17) Uani 1 1 d . . .
H28 H 0.2482 1.1609 0.4365 0.077 Uiso 1 1 calc R . .
C29 C 0.1948(3) 1.0266(7) 0.3465(4) 0.0659(18) Uani 1 1 d . . .
H29 H 0.1950 1.0807 0.3086 0.079 Uiso 1 1 calc R . .
C30 C 0.1630(3) 0.8988(6) 0.3232(3) 0.0545(16) Uani 1 1 d . . .
H30 H 0.1429 0.8670 0.2708 0.065 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 C1 1.238(6) . ?
C1 C9 1.462(7) . ?
C1 C2 1.490(7) . ?
C2 C3 1.383(7) . ?
C2 C7 1.400(7) . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.348(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.481(6) . ?
C8 C18 1.516(6) . ?
C8 C9 1.523(7) . ?
C8 H8 0.9800 . ?
C9 C10 1.361(7) . ?
C10 C11 1.464(7) . ?
C10 C25 1.508(7) . ?
C11 C12 1.416(7) . ?
C11 C16 1.442(7) . ?
C12 C13 1.374(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.489(7) . ?
C17 C18 1.310(6) . ?
C17 C19 1.519(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(6) . ?
C19 C24 1.388(7) . ?
C20 C21 1.381(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.379(7) . ?
C25 C26 1.409(7) . ?
C26 C27 1.394(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.400(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.354(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(8) . ?
C29 H29 0.9300 . ?
C30 H30 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
O1 C1 C9 129.7(5) . . ?
O1 C1 C2 123.8(5) . . ?
C9 C1 C2 106.5(5) . . ?
C3 C2 C7 121.0(5) . . ?
C3 C2 C1 130.4(6) . . ?
C7 C2 C1 108.6(5) . . ?
C4 C3 C2 118.4(6) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 121.8(5) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 118.1(6) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 119.6(5) . . ?
C6 C7 C8 128.7(5) . . ?
C2 C7 C8 111.7(5) . . ?
C7 C8 C18 113.7(4) . . ?
C7 C8 C9 103.4(4) . . ?
C18 C8 C9 107.5(4) . . ?
C7 C8 H8 110.7 . . ?
C18 C8 H8 110.7 . . ?
C9 C8 H8 110.7 . . ?
C10 C9 C1 130.2(5) . . ?
C10 C9 C8 121.1(5) . . ?
C1 C9 C8 108.6(5) . . ?
C9 C10 C11 121.6(5) . . ?
C9 C10 C25 122.0(5) . . ?
C11 C10 C25 116.3(5) . . ?
C12 C11 C16 116.6(5) . . ?
C12 C11 C10 118.3(5) . . ?
C16 C11 C10 124.9(5) . . ?
C13 C12 C11 122.5(5) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12 C13 C14 119.5(6) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 122.7(6) . . ?
C14 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C11 118.7(5) . . ?
C15 C16 C17 119.4(5) . . ?
C11 C16 C17 121.9(5) . . ?
C18 C17 C16 123.5(5) . . ?
C18 C17 C19 119.4(5) . . ?
C16 C17 C19 117.0(4) . . ?
C17 C18 C8 123.9(5) . . ?
C17 C18 H18 118.1 . . ?
C8 C18 H18 118.1 . . ?
C20 C19 C24 117.7(5) . . ?
C20 C19 C17 121.0(5) . . ?
C24 C19 C17 121.0(5) . . ?
C19 C20 C21 120.7(5) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.4(6) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 118.9(6) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C19 122.3(5) . . ?
C23 C24 H24 118.8 . . ?
C19 C24 H24 118.8 . . ?
C30 C25 C26 120.0(5) . . ?
C30 C25 C10 121.5(5) . . ?
C26 C25 C10 118.4(5) . . ?
C27 C26 C25 119.1(5) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C26 C27 C28 120.3(6) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 118.7(6) . . ?
C29 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
C28 C29 C30 122.8(6) . . ?
C28 C29 H29 118.6 . . ?
C30 C29 H29 118.6 . . ?
C25 C30 C29 119.0(6) . . ?
C25 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?

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
O1 C1 C2 C3 -2.8(9) . . . . ?
C9 C1 C2 C3 175.9(5) . . . . ?
O1 C1 C2 C7 176.5(5) . . . . ?
C9 C1 C2 C7 -4.8(6) . . . . ?
C7 C2 C3 C4 3.8(8) . . . . ?
C1 C2 C3 C4 -177.0(5) . . . . ?
C2 C3 C4 C5 0.7(9) . . . . ?
C3 C4 C5 C6 -4.1(9) . . . . ?
C4 C5 C6 C7 3.0(9) . . . . ?
C5 C6 C7 C2 1.4(8) . . . . ?
C5 C6 C7 C8 179.5(5) . . . . ?
C3 C2 C7 C6 -4.8(8) . . . . ?
C1 C2 C7 C6 175.9(5) . . . . ?
C3 C2 C7 C8 176.7(4) . . . . ?
C1 C2 C7 C8 -2.6(6) . . . . ?
C6 C7 C8 C18 74.0(7) . . . . ?
C2 C7 C8 C18 -107.7(5) . . . . ?
C6 C7 C8 C9 -169.8(5) . . . . ?
C2 C7 C8 C9 8.6(6) . . . . ?
O1 C1 C9 C10 6.1(9) . . . . ?
C2 C1 C9 C10 -172.5(5) . . . . ?
O1 C1 C9 C8 -171.2(6) . . . . ?
C2 C1 C9 C8 10.2(5) . . . . ?
C7 C8 C9 C10 171.0(5) . . . . ?
C18 C8 C9 C10 -68.5(6) . . . . ?
C7 C8 C9 C1 -11.4(5) . . . . ?
C18 C8 C9 C1 109.2(5) . . . . ?
C1 C9 C10 C11 -174.0(5) . . . . ?
C8 C9 C10 C11 3.1(8) . . . . ?
C1 C9 C10 C25 10.7(8) . . . . ?
C8 C9 C10 C25 -172.2(5) . . . . ?
C9 C10 C11 C12 -140.1(5) . . . . ?
C25 C10 C11 C12 35.4(7) . . . . ?
C9 C10 C11 C16 43.9(8) . . . . ?
C25 C10 C11 C16 -140.5(5) . . . . ?
C16 C11 C12 C13 -1.2(8) . . . . ?
C10 C11 C12 C13 -177.5(5) . . . . ?
C11 C12 C13 C14 2.8(9) . . . . ?
C12 C13 C14 C15 -1.6(10) . . . . ?
C13 C14 C15 C16 -1.2(10) . . . . ?
C14 C15 C16 C11 2.7(9) . . . . ?
C14 C15 C16 C17 -175.0(5) . . . . ?
C12 C11 C16 C15 -1.5(7) . . . . ?
C10 C11 C16 C15 174.5(5) . . . . ?
C12 C11 C16 C17 176.1(5) . . . . ?
C10 C11 C16 C17 -7.8(8) . . . . ?
C15 C16 C17 C18 139.3(6) . . . . ?
C11 C16 C17 C18 -38.4(8) . . . . ?
C15 C16 C17 C19 -38.3(7) . . . . ?
C11 C16 C17 C19 144.1(5) . . . . ?
C16 C17 C18 C8 4.2(8) . . . . ?
C19 C17 C18 C8 -178.3(4) . . . . ?
C7 C8 C18 C17 177.3(5) . . . . ?
C9 C8 C18 C17 63.5(6) . . . . ?
C18 C17 C19 C20 135.6(5) . . . . ?
C16 C17 C19 C20 -46.8(7) . . . . ?
C18 C17 C19 C24 -37.8(7) . . . . ?
C16 C17 C19 C24 139.8(5) . . . . ?
C24 C19 C20 C21 2.0(8) . . . . ?
C17 C19 C20 C21 -171.6(5) . . . . ?
C19 C20 C21 C22 -1.0(8) . . . . ?
C20 C21 C22 C23 0.4(9) . . . . ?
C21 C22 C23 C24 -1.0(9) . . . . ?
C22 C23 C24 C19 2.2(9) . . . . ?
C20 C19 C24 C23 -2.7(8) . . . . ?
C17 C19 C24 C23 170.9(5) . . . . ?
C9 C10 C25 C30 52.8(8) . . . . ?
C11 C10 C25 C30 -122.8(6) . . . . ?
C9 C10 C25 C26 -131.8(5) . . . . ?
C11 C10 C25 C26 52.7(7) . . . . ?
C30 C25 C26 C27 -1.6(8) . . . . ?
C10 C25 C26 C27 -177.1(5) . . . . ?
C25 C26 C27 C28 0.2(9) . . . . ?
C26 C27 C28 C29 1.8(9) . . . . ?
C27 C28 C29 C30 -2.6(10) . . . . ?
C26 C25 C30 C29 0.9(9) . . . . ?
C10 C25 C30 C29 176.2(5) . . . . ?
C28 C29 C30 C25 1.3(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_zhanghl_0313
_database_code_depnum_ccdc_archive 'CCDC 1996333'
loop_
_audit_author_name
_audit_author_address
zhuhaitao-b
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2020-04-11 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;
_audit_creation_date             2019-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H25 Cl S'
_chemical_formula_sum            'C36 H25 Cl S'
_chemical_formula_weight         525.07
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7240(7)
_cell_length_b                   11.3771(7)
_cell_length_c                   17.1290(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.235(5)
_cell_angle_gamma                90
_cell_volume                     2658.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5890
_cell_measurement_theta_min      3.7750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10498
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.455
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -98.00  -55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   38.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -43.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000   90.0000 140

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00  -25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  -60.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0327712000
_diffrn_orient_matrix_UB_12      -0.0466363000
_diffrn_orient_matrix_UB_13      -0.0113990000
_diffrn_orient_matrix_UB_21      0.0139589000
_diffrn_orient_matrix_UB_22      0.0024367000
_diffrn_orient_matrix_UB_23      -0.0386563000
_diffrn_orient_matrix_UB_31      0.0378874000
_diffrn_orient_matrix_UB_32      -0.0412563000
_diffrn_orient_matrix_UB_33      0.0105716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3300
_reflns_number_total             5208
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.3363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1326
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.51888(6) 0.27444(9) 0.19041(6) 0.0866(3) Uani 1 1 d . . . . .
S1 S 0.33136(5) 0.70067(7) -0.00190(5) 0.0554(2) Uani 1 1 d . . . . .
C1 C 0.11336(16) 0.7191(2) 0.20349(14) 0.0359(6) Uani 1 1 d . . . . .
C2 C 0.05144(18) 0.8040(2) 0.23112(16) 0.0465(7) Uani 1 1 d . . . . .
H2 H 0.042213 0.875006 0.204472 0.056 Uiso 1 1 calc R . . . .
C3 C 0.00393(19) 0.7847(3) 0.29679(17) 0.0533(8) Uani 1 1 d . . . . .
H3 H -0.038579 0.841261 0.312809 0.064 Uiso 1 1 calc R . . . .
C4 C 0.01912(19) 0.6821(3) 0.33871(17) 0.0550(8) Uani 1 1 d . . . . .
H4 H -0.014003 0.668227 0.382375 0.066 Uiso 1 1 calc R . . . .
C5 C 0.08368(17) 0.6003(3) 0.31552(15) 0.0464(7) Uani 1 1 d . . . . .
H5 H 0.096531 0.533038 0.345759 0.056 Uiso 1 1 calc R . . . .
C6 C 0.13075(16) 0.6152(2) 0.24757(14) 0.0360(6) Uani 1 1 d . . . . .
C7 C 0.19762(16) 0.5201(2) 0.22690(14) 0.0332(6) Uani 1 1 d . . . . .
C8 C 0.19662(16) 0.4827(2) 0.15276(14) 0.0333(6) Uani 1 1 d . . . . .
H8 H 0.238955 0.422465 0.141908 0.040 Uiso 1 1 calc R . . . .
C9 C 0.12967(16) 0.5343(2) 0.08651(14) 0.0340(6) Uani 1 1 d . . . . .
H9 H 0.061939 0.532702 0.099640 0.041 Uiso 1 1 calc R . . . .
C10 C 0.16091(16) 0.6609(2) 0.07430(14) 0.0350(6) Uani 1 1 d . . . . .
C11 C 0.15482(16) 0.7443(2) 0.12844(15) 0.0354(6) Uani 1 1 d . . . . .
C12 C 0.19837(18) 0.6713(2) -0.00555(14) 0.0403(6) Uani 1 1 d . . . . .
H12 H 0.162665 0.734724 -0.034904 0.048 Uiso 1 1 calc R . . . .
C13 C 0.16970(17) 0.5565(2) -0.04451(15) 0.0399(6) Uani 1 1 d . . . . .
C14 C 0.13478(17) 0.4790(2) 0.00767(14) 0.0371(6) Uani 1 1 d . . . . .
C15 C 0.11085(18) 0.3650(2) -0.01514(16) 0.0468(7) Uani 1 1 d . . . . .
H15 H 0.088186 0.312239 0.020225 0.056 Uiso 1 1 calc R . . . .
C16 C 0.1212(2) 0.3304(3) -0.09161(17) 0.0577(8) Uani 1 1 d . . . . .
H16 H 0.106410 0.253635 -0.107339 0.069 Uiso 1 1 calc R . . . .
C17 C 0.1532(2) 0.4096(3) -0.14439(17) 0.0617(9) Uani 1 1 d . . . . .
H17 H 0.157392 0.386381 -0.195975 0.074 Uiso 1 1 calc R . . . .
C18 C 0.1791(2) 0.5226(3) -0.12165(16) 0.0542(8) Uani 1 1 d . . . . .
H18 H 0.202340 0.575128 -0.156917 0.065 Uiso 1 1 calc R . . . .
C19 C 0.18510(18) 0.8680(2) 0.11480(16) 0.0424(6) Uani 1 1 d . . . . .
C20 C 0.1418(2) 0.9334(3) 0.05241(18) 0.0608(8) Uani 1 1 d . . . . .
H20 H 0.090727 0.900769 0.019268 0.073 Uiso 1 1 calc R . . . .
C21 C 0.1727(3) 1.0455(3) 0.0383(2) 0.0798(11) Uani 1 1 d . . . . .
H21 H 0.143150 1.087543 -0.004433 0.096 Uiso 1 1 calc R . . . .
C22 C 0.2463(3) 1.0951(3) 0.0868(3) 0.0896(12) Uani 1 1 d . . . . .
H22 H 0.267461 1.170785 0.076953 0.107 Uiso 1 1 calc R . . . .
C23 C 0.2896(3) 1.0334(3) 0.1505(3) 0.0887(12) Uani 1 1 d . . . . .
H23 H 0.339427 1.067884 0.183936 0.106 Uiso 1 1 calc R . . . .
C24 C 0.2590(2) 0.9196(3) 0.1650(2) 0.0647(9) Uani 1 1 d . . . . .
H24 H 0.288059 0.878284 0.208237 0.078 Uiso 1 1 calc R . . . .
C25 C 0.26765(16) 0.4700(2) 0.29028(14) 0.0374(6) Uani 1 1 d . . . . .
C26 C 0.31604(19) 0.5420(3) 0.34694(15) 0.0518(7) Uani 1 1 d . . . . .
H26 H 0.300102 0.621407 0.348270 0.062 Uiso 1 1 calc R . . . .
C27 C 0.3883(2) 0.4967(3) 0.40187(18) 0.0695(10) Uani 1 1 d . . . . .
H27 H 0.420960 0.546363 0.439098 0.083 Uiso 1 1 calc R . . . .
C28 C 0.4117(2) 0.3803(3) 0.40178(19) 0.0723(10) Uani 1 1 d . . . . .
H28 H 0.460789 0.350753 0.438242 0.087 Uiso 1 1 calc R . . . .
C29 C 0.3626(2) 0.3073(3) 0.34773(19) 0.0651(9) Uani 1 1 d . . . . .
H29 H 0.377567 0.227542 0.348129 0.078 Uiso 1 1 calc R . . . .
C30 C 0.2907(2) 0.3509(3) 0.29232(16) 0.0498(7) Uani 1 1 d . . . . .
H30 H 0.257430 0.300122 0.256139 0.060 Uiso 1 1 calc R . . . .
C31 C 0.38100(17) 0.5787(2) 0.05265(16) 0.0441(7) Uani 1 1 d . . . . .
C32 C 0.38563(17) 0.4691(3) 0.01874(16) 0.0463(7) Uani 1 1 d . . . . .
H32 H 0.361049 0.458515 -0.033550 0.056 Uiso 1 1 calc R . . . .
C33 C 0.42622(18) 0.3750(3) 0.06139(17) 0.0508(7) Uani 1 1 d . . . . .
H33 H 0.427220 0.300863 0.038613 0.061 Uiso 1 1 calc R . . . .
C34 C 0.46524(18) 0.3920(3) 0.13801(17) 0.0513(7) Uani 1 1 d . . . . .
C35 C 0.46206(19) 0.5003(3) 0.17267(18) 0.0568(8) Uani 1 1 d . . . . .
H35 H 0.488572 0.511116 0.224484 0.068 Uiso 1 1 calc R . . . .
C36 C 0.41930(18) 0.5930(3) 0.13011(17) 0.0523(7) Uani 1 1 d . . . . .
H36 H 0.416125 0.666264 0.153783 0.063 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 C34 1.730(3) . ?
S1 C12 1.850(3) . ?
S1 C31 1.768(3) . ?
C1 C2 1.402(3) . ?
C1 C6 1.409(3) . ?
C1 C11 1.489(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(3) . ?
C6 C7 1.486(3) . ?
C7 C8 1.338(3) . ?
C7 C25 1.484(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.500(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.523(3) . ?
C9 C14 1.498(3) . ?
C10 C11 1.336(3) . ?
C10 C12 1.517(3) . ?
C11 C19 1.493(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.499(3) . ?
C13 C14 1.378(3) . ?
C13 C18 1.396(4) . ?
C14 C15 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(4) . ?
C19 C24 1.387(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.359(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.392(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(3) . ?
C25 C30 1.391(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.390(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.363(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.385(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(4) . ?
C31 C36 1.383(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.379(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.376(4) . ?
C34 C35 1.371(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.377(4) . ?
C36 H36 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
C31 S1 C12 101.43(11) . . ?
C2 C1 C6 118.1(2) . . ?
C2 C1 C11 117.5(2) . . ?
C6 C1 C11 124.4(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 123.8(2) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 117.5(2) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 C25 120.7(2) . . ?
C25 C7 C6 118.2(2) . . ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.4(2) . . ?
C9 C8 H8 118.8 . . ?
C8 C9 H9 109.7 . . ?
C8 C9 C10 108.39(18) . . ?
C10 C9 H9 109.7 . . ?
C14 C9 C8 115.6(2) . . ?
C14 C9 H9 109.7 . . ?
C14 C9 C10 103.4(2) . . ?
C11 C10 C9 122.5(2) . . ?
C11 C10 C12 128.5(2) . . ?
C12 C10 C9 109.0(2) . . ?
C1 C11 C19 117.1(2) . . ?
C10 C11 C1 121.4(2) . . ?
C10 C11 C19 121.4(2) . . ?
S1 C12 H12 108.7 . . ?
C10 C12 S1 114.41(16) . . ?
C10 C12 H12 108.7 . . ?
C13 C12 S1 112.50(17) . . ?
C13 C12 C10 103.6(2) . . ?
C13 C12 H12 108.7 . . ?
C14 C13 C12 111.2(2) . . ?
C14 C13 C18 120.8(3) . . ?
C18 C13 C12 127.9(3) . . ?
C13 C14 C9 111.7(2) . . ?
C13 C14 C15 120.3(2) . . ?
C15 C14 C9 128.0(3) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.1(3) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 120.7 . . ?
C17 C18 C13 118.5(3) . . ?
C17 C18 H18 120.7 . . ?
C20 C19 C11 121.7(2) . . ?
C20 C19 C24 118.4(3) . . ?
C24 C19 C11 120.0(2) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 119.9(3) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C7 120.6(2) . . ?
C26 C25 C30 118.0(2) . . ?
C30 C25 C7 121.3(2) . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.5(3) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 H30 119.7 . . ?
C29 C30 C25 120.6(3) . . ?
C29 C30 H30 119.7 . . ?
C32 C31 S1 121.3(2) . . ?
C32 C31 C36 118.7(3) . . ?
C36 C31 S1 120.0(2) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 C31 120.9(3) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 H33 120.4 . . ?
C34 C33 C32 119.3(3) . . ?
C34 C33 H33 120.4 . . ?
C33 C34 Cl1 119.1(3) . . ?
C35 C34 Cl1 120.1(2) . . ?
C35 C34 C33 120.8(3) . . ?
C34 C35 H35 120.3 . . ?
C34 C35 C36 119.4(3) . . ?
C36 C35 H35 120.3 . . ?
C31 C36 H36 119.5 . . ?
C35 C36 C31 120.9(3) . . ?
C35 C36 H36 119.5 . . ?

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
Cl1 C34 C35 C36 179.9(2) . . . . ?
S1 C12 C13 C14 115.2(2) . . . . ?
S1 C12 C13 C18 -61.7(3) . . . . ?
S1 C31 C32 C33 178.73(19) . . . . ?
S1 C31 C36 C35 -177.2(2) . . . . ?
C1 C2 C3 C4 2.3(4) . . . . ?
C1 C6 C7 C8 -44.1(3) . . . . ?
C1 C6 C7 C25 134.2(2) . . . . ?
C1 C11 C19 C20 -118.3(3) . . . . ?
C1 C11 C19 C24 62.3(3) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -177.6(2) . . . . ?
C2 C1 C11 C10 -138.7(2) . . . . ?
C2 C1 C11 C19 38.6(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -3.6(4) . . . . ?
C4 C5 C6 C1 2.1(4) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
C5 C6 C7 C8 136.7(2) . . . . ?
C5 C6 C7 C25 -45.0(3) . . . . ?
C6 C1 C2 C3 -3.8(4) . . . . ?
C6 C1 C11 C10 40.1(3) . . . . ?
C6 C1 C11 C19 -142.6(2) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C6 C7 C25 C26 -40.4(3) . . . . ?
C6 C7 C25 C30 143.1(2) . . . . ?
C7 C8 C9 C10 67.0(3) . . . . ?
C7 C8 C9 C14 -177.5(2) . . . . ?
C7 C25 C26 C27 -174.0(3) . . . . ?
C7 C25 C30 C29 174.2(2) . . . . ?
C8 C7 C25 C26 137.9(3) . . . . ?
C8 C7 C25 C30 -38.6(4) . . . . ?
C8 C9 C10 C11 -65.1(3) . . . . ?
C8 C9 C10 C12 114.4(2) . . . . ?
C8 C9 C14 C13 -115.0(2) . . . . ?
C8 C9 C14 C15 63.9(3) . . . . ?
C9 C10 C11 C1 -2.2(3) . . . . ?
C9 C10 C11 C19 -179.5(2) . . . . ?
C9 C10 C12 S1 -112.04(19) . . . . ?
C9 C10 C12 C13 10.8(2) . . . . ?
C9 C14 C15 C16 -179.8(2) . . . . ?
C10 C9 C14 C13 3.3(2) . . . . ?
C10 C9 C14 C15 -177.8(2) . . . . ?
C10 C11 C19 C20 59.0(4) . . . . ?
C10 C11 C19 C24 -120.4(3) . . . . ?
C10 C12 C13 C14 -8.9(3) . . . . ?
C10 C12 C13 C18 174.3(2) . . . . ?
C11 C1 C2 C3 175.1(2) . . . . ?
C11 C1 C6 C5 -177.2(2) . . . . ?
C11 C1 C6 C7 3.7(4) . . . . ?
C11 C10 C12 S1 67.4(3) . . . . ?
C11 C10 C12 C13 -169.8(2) . . . . ?
C11 C19 C20 C21 -177.4(3) . . . . ?
C11 C19 C24 C23 177.6(3) . . . . ?
C12 S1 C31 C32 76.9(2) . . . . ?
C12 S1 C31 C36 -105.4(2) . . . . ?
C12 C10 C11 C1 178.4(2) . . . . ?
C12 C10 C11 C19 1.1(4) . . . . ?
C12 C13 C14 C9 3.6(3) . . . . ?
C12 C13 C14 C15 -175.4(2) . . . . ?
C12 C13 C18 C17 176.2(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C9 C10 C11 171.6(2) . . . . ?
C14 C9 C10 C12 -8.9(2) . . . . ?
C14 C13 C18 C17 -0.4(4) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C16 C17 C18 2.5(4) . . . . ?
C16 C17 C18 C13 -1.7(4) . . . . ?
C18 C13 C14 C9 -179.3(2) . . . . ?
C18 C13 C14 C15 1.7(4) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C20 C19 C24 C23 -1.8(5) . . . . ?
C20 C21 C22 C23 -0.5(6) . . . . ?
C21 C22 C23 C24 0.8(6) . . . . ?
C22 C23 C24 C19 0.4(6) . . . . ?
C24 C19 C20 C21 2.1(5) . . . . ?
C25 C7 C8 C9 -177.6(2) . . . . ?
C25 C26 C27 C28 -1.0(5) . . . . ?
C26 C25 C30 C29 -2.4(4) . . . . ?
C26 C27 C28 C29 -0.9(5) . . . . ?
C27 C28 C29 C30 1.2(5) . . . . ?
C28 C29 C30 C25 0.5(5) . . . . ?
C30 C25 C26 C27 2.7(4) . . . . ?
C31 S1 C12 C10 58.1(2) . . . . ?
C31 S1 C12 C13 -59.7(2) . . . . ?
C31 C32 C33 C34 -2.0(4) . . . . ?
C32 C31 C36 C35 0.6(4) . . . . ?
C32 C33 C34 Cl1 -178.35(19) . . . . ?
C32 C33 C34 C35 1.5(4) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C34 C35 C36 C31 -1.0(4) . . . . ?
C36 C31 C32 C33 1.0(4) . . . . ?

_olex2_date_sample_data_collection 2019-03-14
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_222
_database_code_depnum_ccdc_archive 'CCDC 1996334'
loop_
_audit_author_name
_audit_author_address
zhuhaitao-c
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2020-04-11 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;
_audit_creation_date             2019-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 O2'
_chemical_formula_sum            'C24 H20 O2'
_chemical_formula_weight         340.40
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0194(5)
_cell_length_b                   12.1077(6)
_cell_length_c                   14.8611(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.4640(10)
_cell_angle_gamma                90
_cell_volume                     1845.25(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.330
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28564
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_min         3.330
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3229
_reflns_number_total             4230
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.3570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1375
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C14(H14), C17(H17), C15(H15), C16(H16), C6(H6), C3(H3),
 C24(H24), C20(H20), C7(H7), C22(H22), C23(H23), C21(H21)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O2 O 0.49406(9) 0.00944(7) 0.27169(6) 0.0398(2) Uani 1 1 d . . . . .
O1 O 0.39224(12) 0.31407(9) 0.42926(8) 0.0661(3) Uani 1 1 d . . . . .
C11 C 0.28837(12) 0.09435(11) 0.26560(9) 0.0388(3) Uani 1 1 d . . . . .
C9 C 0.48045(13) 0.14126(10) 0.39821(9) 0.0380(3) Uani 1 1 d . . . . .
C10 C 0.42072(12) 0.04856(10) 0.32691(9) 0.0367(3) Uani 1 1 d . . . . .
H10 H 0.406372 -0.014154 0.363510 0.044 Uiso 1 1 calc R . . . .
C8 C 0.59650(13) 0.15280(11) 0.46981(9) 0.0410(3) Uani 1 1 d . . . . .
H8 H 0.606831 0.220081 0.501953 0.049 Uiso 1 1 calc R . . . .
C12 C 0.26552(13) 0.19624(11) 0.29850(9) 0.0405(3) Uani 1 1 d . . . . .
C5 C 0.70988(13) 0.08069(11) 0.50731(9) 0.0413(3) Uani 1 1 d . . . . .
C13 C 0.38056(14) 0.23020(11) 0.38146(10) 0.0436(3) Uani 1 1 d . . . . .
C18 C 0.52914(17) 0.09074(12) 0.21750(12) 0.0558(4) Uani 1 1 d . . . . .
H18A H 0.580426 0.147801 0.260509 0.067 Uiso 1 1 calc R . . . .
H18B H 0.451098 0.124743 0.171978 0.067 Uiso 1 1 calc R . . . .
C4 C 0.71626(15) -0.02574(12) 0.47421(11) 0.0492(3) Uani 1 1 d . . . . .
H4 H 0.645077 -0.054755 0.424160 0.059 Uiso 1 1 calc R . . . .
C14 C 0.14771(14) 0.25174(13) 0.25421(11) 0.0500(4) Uani 1 1 d . . . . .
H14 H 0.132346 0.319653 0.277299 0.060 Uiso 1 1 calc R . . . .
C17 C 0.19426(14) 0.04584(13) 0.18606(11) 0.0501(4) Uani 1 1 d . . . . .
H17 H 0.208920 -0.022429 0.163211 0.060 Uiso 1 1 calc R . . . .
C19 C 0.60656(14) 0.03988(12) 0.16385(10) 0.0459(3) Uani 1 1 d . . . . .
C2 C 0.93567(15) -0.04947(15) 0.58957(12) 0.0585(4) Uani 1 1 d . . . . .
C15 C 0.05491(15) 0.20290(14) 0.17530(11) 0.0562(4) Uani 1 1 d . . . . .
H15 H -0.024300 0.238411 0.144259 0.067 Uiso 1 1 calc R . . . .
C16 C 0.07806(15) 0.10145(14) 0.14154(11) 0.0570(4) Uani 1 1 d . . . . .
H16 H 0.014152 0.070137 0.087863 0.068 Uiso 1 1 calc R . . . .
C6 C 0.81801(15) 0.11920(15) 0.58352(12) 0.0576(4) Uani 1 1 d . . . . .
H6 H 0.815807 0.189444 0.608195 0.069 Uiso 1 1 calc R . . . .
C3 C 0.82753(16) -0.08877(14) 0.51510(12) 0.0590(4) Uani 1 1 d . . . . .
H3 H 0.829627 -0.159740 0.491772 0.071 Uiso 1 1 calc R . . . .
C24 C 0.66048(18) -0.06400(15) 0.18432(14) 0.0662(5) Uani 1 1 d . . . . .
H24 H 0.647697 -0.106264 0.232355 0.079 Uiso 1 1 calc R . . . .
C1 C 1.05700(17) -0.1190(2) 0.63166(16) 0.0835(6) Uani 1 1 d . . . . .
H1A H 1.034961 -0.195451 0.618066 0.125 Uiso 1 1 calc GR . . . .
H1B H 1.094224 -0.108049 0.700362 0.125 Uiso 1 1 calc GR . . . .
H1C H 1.119036 -0.097614 0.603353 0.125 Uiso 1 1 calc GR . . . .
C20 C 0.62548(19) 0.09895(16) 0.09143(14) 0.0699(5) Uani 1 1 d . . . . .
H20 H 0.587862 0.168470 0.075391 0.084 Uiso 1 1 calc R . . . .
C7 C 0.92876(16) 0.05522(17) 0.62338(13) 0.0679(5) Uani 1 1 d . . . . .
H7 H 0.999866 0.083453 0.673962 0.081 Uiso 1 1 calc R . . . .
C22 C 0.7531(2) -0.0450(2) 0.06264(17) 0.0852(7) Uani 1 1 d . . . . .
H22 H 0.802545 -0.073332 0.028950 0.102 Uiso 1 1 calc R . . . .
C23 C 0.7338(2) -0.10586(18) 0.13361(17) 0.0817(6) Uani 1 1 d . . . . .
H23 H 0.770121 -0.176013 0.148055 0.098 Uiso 1 1 calc R . . . .
C21 C 0.6997(2) 0.0568(2) 0.04180(17) 0.0901(7) Uani 1 1 d . . . . .
H21 H 0.712893 0.098760 -0.006231 0.108 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
O2 C10 1.4269(15) . ?
O2 C18 1.4124(16) . ?
O1 C13 1.2188(17) . ?
C11 C10 1.5139(18) . ?
C11 C12 1.3836(19) . ?
C11 C17 1.3858(19) . ?
C9 C10 1.5183(18) . ?
C9 C8 1.3384(19) . ?
C9 C13 1.4942(18) . ?
C10 H10 0.9800 . ?
C8 H8 0.9300 . ?
C8 C5 1.4574(19) . ?
C12 C13 1.4670(19) . ?
C12 C14 1.3946(19) . ?
C5 C4 1.390(2) . ?
C5 C6 1.390(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.497(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.382(2) . ?
C19 C24 1.377(2) . ?
C19 C20 1.370(2) . ?
C2 C3 1.381(2) . ?
C2 C1 1.508(2) . ?
C2 C7 1.376(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.382(2) . ?
C3 H3 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.387(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C7 H7 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.365(3) . ?
C22 C21 1.352(3) . ?
C23 H23 0.9300 . ?
C21 H21 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
C18 O2 C10 115.29(10) . . ?
C12 C11 C10 111.94(11) . . ?
C12 C11 C17 120.21(13) . . ?
C17 C11 C10 127.85(13) . . ?
C8 C9 C10 132.54(12) . . ?
C8 C9 C13 119.24(12) . . ?
C13 C9 C10 108.16(11) . . ?
O2 C10 C11 113.52(10) . . ?
O2 C10 C9 117.04(10) . . ?
O2 C10 H10 107.6 . . ?
C11 C10 C9 103.03(10) . . ?
C11 C10 H10 107.6 . . ?
C9 C10 H10 107.6 . . ?
C9 C8 H8 113.7 . . ?
C9 C8 C5 132.64(13) . . ?
C5 C8 H8 113.7 . . ?
C11 C12 C13 109.50(11) . . ?
C11 C12 C14 121.41(13) . . ?
C14 C12 C13 129.08(13) . . ?
C4 C5 C8 124.56(12) . . ?
C6 C5 C8 118.03(13) . . ?
C6 C5 C4 117.38(13) . . ?
O1 C13 C9 126.10(13) . . ?
O1 C13 C12 126.71(13) . . ?
C12 C13 C9 107.18(11) . . ?
O2 C18 H18A 109.6 . . ?
O2 C18 H18B 109.6 . . ?
O2 C18 C19 110.19(12) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.52(15) . . ?
C3 C4 H4 119.7 . . ?
C12 C14 H14 121.0 . . ?
C15 C14 C12 117.92(14) . . ?
C15 C14 H14 121.0 . . ?
C11 C17 H17 120.8 . . ?
C16 C17 C11 118.35(14) . . ?
C16 C17 H17 120.8 . . ?
C24 C19 C18 122.84(13) . . ?
C20 C19 C18 118.94(15) . . ?
C20 C19 C24 118.23(15) . . ?
C3 C2 C1 120.95(18) . . ?
C7 C2 C3 117.60(15) . . ?
C7 C2 C1 121.44(18) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.79(14) . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 121.30(14) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.35(16) . . ?
C7 C6 H6 119.3 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 121.93(16) . . ?
C2 C3 H3 119.0 . . ?
C19 C24 H24 119.9 . . ?
C19 C24 C23 120.27(18) . . ?
C23 C24 H24 119.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.04(19) . . ?
C21 C20 H20 119.5 . . ?
C2 C7 C6 121.19(16) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.41(17) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.45(19) . . ?
C22 C21 H21 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
O2 C18 C19 C24 -14.4(2) . . . . ?
O2 C18 C19 C20 165.92(14) . . . . ?
C11 C12 C13 O1 -178.00(14) . . . . ?
C11 C12 C13 C9 0.71(15) . . . . ?
C11 C12 C14 C15 -1.1(2) . . . . ?
C11 C17 C16 C15 -0.4(2) . . . . ?
C9 C8 C5 C4 -2.9(2) . . . . ?
C9 C8 C5 C6 179.24(15) . . . . ?
C10 O2 C18 C19 179.40(11) . . . . ?
C10 C11 C12 C13 2.18(15) . . . . ?
C10 C11 C12 C14 -178.03(12) . . . . ?
C10 C11 C17 C16 178.60(13) . . . . ?
C10 C9 C8 C5 -0.4(2) . . . . ?
C10 C9 C13 O1 175.47(14) . . . . ?
C10 C9 C13 C12 -3.26(14) . . . . ?
C8 C9 C10 O2 -53.22(19) . . . . ?
C8 C9 C10 C11 -178.52(14) . . . . ?
C8 C9 C13 O1 -2.2(2) . . . . ?
C8 C9 C13 C12 179.12(12) . . . . ?
C8 C5 C4 C3 -179.13(13) . . . . ?
C8 C5 C6 C7 179.52(14) . . . . ?
C12 C11 C10 O2 -131.60(11) . . . . ?
C12 C11 C10 C9 -4.04(13) . . . . ?
C12 C11 C17 C16 -0.4(2) . . . . ?
C12 C14 C15 C16 0.3(2) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C13 C9 C10 O2 129.60(11) . . . . ?
C13 C9 C10 C11 4.30(13) . . . . ?
C13 C9 C8 C5 176.49(13) . . . . ?
C13 C12 C14 C15 178.68(13) . . . . ?
C18 O2 C10 C11 63.92(15) . . . . ?
C18 O2 C10 C9 -55.96(15) . . . . ?
C18 C19 C24 C23 -178.54(17) . . . . ?
C18 C19 C20 C21 178.01(18) . . . . ?
C4 C5 C6 C7 1.5(2) . . . . ?
C14 C12 C13 O1 2.2(2) . . . . ?
C14 C12 C13 C9 -179.06(13) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C17 C11 C10 O2 49.37(18) . . . . ?
C17 C11 C10 C9 176.93(13) . . . . ?
C17 C11 C12 C13 -178.71(12) . . . . ?
C17 C11 C12 C14 1.1(2) . . . . ?
C19 C24 C23 C22 -0.2(3) . . . . ?
C19 C20 C21 C22 1.3(3) . . . . ?
C6 C5 C4 C3 -1.2(2) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C24 C19 C20 C21 -1.7(3) . . . . ?
C1 C2 C3 C4 -178.75(15) . . . . ?
C1 C2 C7 C6 178.99(16) . . . . ?
C20 C19 C24 C23 1.2(3) . . . . ?
C7 C2 C3 C4 0.9(2) . . . . ?
C23 C22 C21 C20 -0.3(4) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_wj-20200804-1
_database_code_depnum_ccdc_archive 'CCDC 2021315'
loop_
_audit_author_name
_audit_author_address
zhuhaitao-d
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2020-08-04 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H20 O2'
_chemical_formula_weight         412.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0409(4)
_cell_length_b                   15.3931(4)
_cell_length_c                   13.0070(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.945(4)
_cell_angle_gamma                90
_cell_volume                     2125.54(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.624
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14385
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.555
_diffrn_reflns_theta_max         76.528
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4274
_reflns_number_gt                3720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²+0.3754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4274
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_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_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
O15 O 0.52750(9) 0.08645(7) 0.20020(8) 0.0422(3) Uani 1 1 d . . . . .
O32 O 0.17518(9) 0.14718(6) 0.46138(8) 0.0407(2) Uani 1 1 d . . . . .
C2 C 0.42608(12) 0.07404(8) 0.35118(11) 0.0339(3) Uani 1 1 d . . . . .
H2 H 0.454397 0.012604 0.348274 0.041 Uiso 1 1 calc R U . . .
C5 C 0.27232(12) 0.12234(8) 0.44309(11) 0.0335(3) Uani 1 1 d . . . . .
C16 C 0.06326(11) 0.03133(8) 0.27775(10) 0.0324(3) Uani 1 1 d . . . . .
C17 C 0.03784(13) -0.01921(9) 0.35806(11) 0.0390(3) Uani 1 1 d . . . . .
H17 H 0.105235 -0.046537 0.409314 0.047 Uiso 1 1 calc R U . . .
C20 C -0.15865(13) 0.06115(10) 0.21126(12) 0.0448(3) Uani 1 1 d . . . . .
H20 H -0.226143 0.089548 0.161306 0.054 Uiso 1 1 calc R U . . .
C6 C 0.28705(12) 0.07567(8) 0.34655(10) 0.0321(3) Uani 1 1 d . . . . .
C21 C -0.03629(13) 0.07093(9) 0.20348(11) 0.0397(3) Uani 1 1 d . . . . .
H21 H -0.020753 0.104729 0.147320 0.048 Uiso 1 1 calc R U . . .
C3 C 0.48932(12) 0.11252(8) 0.45937(11) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.44532(12) 0.12426(9) 0.25675(11) 0.0357(3) Uani 1 1 d . . . . .
H1 H 0.446457 0.189037 0.262752 0.043 Uiso 1 1 calc R U . . .
C9 C 0.15488(14) -0.09134(9) 0.15131(11) 0.0392(3) Uani 1 1 d . . . . .
H9 H 0.081774 -0.101172 0.174742 0.047 Uiso 1 1 calc R U . . .
C8 C 0.22576(12) -0.01574(8) 0.18389(10) 0.0338(3) Uani 1 1 d . . . . .
C22 C 0.61712(13) 0.12657(10) 0.50653(12) 0.0435(3) Uani 1 1 d . . . . .
H22 H 0.678215 0.109437 0.471405 0.052 Uiso 1 1 calc R U . . .
C13 C 0.32713(12) 0.00081(9) 0.13982(11) 0.0354(3) Uani 1 1 d . . . . .
C25 C 0.43736(15) 0.17627(10) 0.61313(12) 0.0444(3) Uani 1 1 d . . . . .
H25 H 0.376496 0.192494 0.648912 0.053 Uiso 1 1 calc R U . . .
C31 C 0.24134(14) 0.12902(9) -0.02763(12) 0.0411(3) Uani 1 1 d . . . . .
H31 H 0.188005 0.082600 -0.019517 0.049 Uiso 1 1 calc R U . . .
C27 C 0.42818(13) 0.21431(10) 0.03847(12) 0.0414(3) Uani 1 1 d . . . . .
H27 H 0.503854 0.226623 0.092273 0.050 Uiso 1 1 calc R U . . .
C18 C -0.08459(13) -0.03019(11) 0.36419(12) 0.0443(3) Uani 1 1 d . . . . .
H18 H -0.100933 -0.065637 0.418665 0.053 Uiso 1 1 calc R U . . .
C10 C 0.18890(15) -0.15201(10) 0.08578(12) 0.0448(3) Uani 1 1 d . . . . .
H10 H 0.139358 -0.202791 0.064823 0.054 Uiso 1 1 calc R U . . .
C12 C 0.36124(14) -0.06174(9) 0.07602(12) 0.0423(3) Uani 1 1 d . . . . .
H12 H 0.431674 -0.051415 0.049076 0.051 Uiso 1 1 calc R U . . .
C4 C 0.40160(13) 0.13787(8) 0.51236(11) 0.0358(3) Uani 1 1 d . . . . .
C11 C 0.29505(16) -0.13876(10) 0.05076(12) 0.0469(4) Uani 1 1 d . . . . .
H11 H 0.322147 -0.182006 0.009891 0.056 Uiso 1 1 calc R U . . .
C26 C 0.35268(12) 0.14487(9) 0.05227(11) 0.0346(3) Uani 1 1 d . . . . .
C24 C 0.56492(16) 0.19005(10) 0.65951(13) 0.0512(4) Uani 1 1 d . . . . .
H24 H 0.592390 0.215984 0.728283 0.061 Uiso 1 1 calc R U . . .
C30 C 0.20783(15) 0.18020(10) -0.11852(12) 0.0471(4) Uani 1 1 d . . . . .
H30 H 0.131790 0.168575 -0.172221 0.057 Uiso 1 1 calc R U . . .
C28 C 0.39423(14) 0.26545(10) -0.05253(13) 0.0462(4) Uani 1 1 d . . . . .
H28 H 0.446479 0.312505 -0.060698 0.055 Uiso 1 1 calc R U . . .
C19 C -0.18290(13) 0.01056(10) 0.29088(13) 0.0450(4) Uani 1 1 d . . . . .
H19 H -0.266831 0.003735 0.295332 0.054 Uiso 1 1 calc R U . . .
C29 C 0.28402(15) 0.24810(10) -0.13186(12) 0.0459(4) Uani 1 1 d . . . . .
H29 H 0.261156 0.282607 -0.194792 0.055 Uiso 1 1 calc R U . . .
C23 C 0.65291(15) 0.16610(11) 0.60584(13) 0.0500(4) Uani 1 1 d . . . . .
H23 H 0.739668 0.177184 0.638232 0.060 Uiso 1 1 calc R U . . .
C14 C 0.39160(12) 0.08798(9) 0.14970(11) 0.0346(3) Uani 1 1 d . . . . .
C7 C 0.19558(12) 0.03703(8) 0.26971(10) 0.0321(3) 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
O15 C1 1.4387(16) . ?
O15 C14 1.4636(15) . ?
O32 C5 1.2220(16) . ?
C2 C3 1.5096(19) . ?
C2 C1 1.5148(18) . ?
C2 C6 1.5197(17) . ?
C2 H2 1.0000 . ?
C5 C4 1.4831(19) . ?
C5 C6 1.4939(18) . ?
C16 C21 1.3891(19) . ?
C16 C17 1.3915(19) . ?
C16 C7 1.4956(17) . ?
C17 C18 1.3862(19) . ?
C17 H17 0.9500 . ?
C20 C19 1.380(2) . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C6 C7 1.3483(18) . ?
C21 H21 0.9500 . ?
C3 C4 1.3899(19) . ?
C3 C22 1.3923(19) . ?
C1 C14 1.466(2) . ?
C1 H1 1.0000 . ?
C9 C10 1.384(2) . ?
C9 C8 1.4015(19) . ?
C9 H9 0.9500 . ?
C8 C13 1.4136(18) . ?
C8 C7 1.4904(18) . ?
C22 C23 1.384(2) . ?
C22 H22 0.9500 . ?
C13 C12 1.3891(19) . ?
C13 C14 1.5078(19) . ?
C25 C24 1.388(2) . ?
C25 C4 1.392(2) . ?
C25 H25 0.9500 . ?
C31 C30 1.384(2) . ?
C31 C26 1.396(2) . ?
C31 H31 0.9500 . ?
C27 C28 1.385(2) . ?
C27 C26 1.3971(19) . ?
C27 H27 0.9500 . ?
C18 C19 1.383(2) . ?
C18 H18 0.9500 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C12 C11 1.384(2) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C26 C14 1.5028(19) . ?
C24 C23 1.393(3) . ?
C24 H24 0.9500 . ?
C30 C29 1.382(2) . ?
C30 H30 0.9500 . ?
C28 C29 1.388(2) . ?
C28 H28 0.9500 . ?
C19 H19 0.9500 . ?
C29 H29 0.9500 . ?
C23 H23 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
C1 O15 C14 60.66(8) . . ?
C3 C2 C1 115.06(11) . . ?
C3 C2 C6 103.53(11) . . ?
C1 C2 C6 108.94(10) . . ?
C3 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
C6 C2 H2 109.7 . . ?
O32 C5 C4 125.51(12) . . ?
O32 C5 C6 128.19(12) . . ?
C4 C5 C6 106.22(11) . . ?
C21 C16 C17 118.89(12) . . ?
C21 C16 C7 121.81(12) . . ?
C17 C16 C7 119.18(11) . . ?
C18 C17 C16 120.82(13) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C20 C21 120.57(13) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C7 C6 C5 127.07(11) . . ?
C7 C6 C2 124.39(12) . . ?
C5 C6 C2 108.46(11) . . ?
C16 C21 C20 120.06(13) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C4 C3 C22 119.86(13) . . ?
C4 C3 C2 111.44(11) . . ?
C22 C3 C2 128.67(13) . . ?
O15 C1 C14 60.51(8) . . ?
O15 C1 C2 117.17(11) . . ?
C14 C1 C2 117.74(11) . . ?
O15 C1 H1 116.6 . . ?
C14 C1 H1 116.6 . . ?
C2 C1 H1 116.6 . . ?
C10 C9 C8 121.54(13) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C8 C13 117.74(12) . . ?
C9 C8 C7 117.25(12) . . ?
C13 C8 C7 124.77(12) . . ?
C23 C22 C3 118.32(15) . . ?
C23 C22 H22 120.8 . . ?
C3 C22 H22 120.8 . . ?
C12 C13 C8 119.48(13) . . ?
C12 C13 C14 117.95(12) . . ?
C8 C13 C14 122.25(12) . . ?
C24 C25 C4 117.75(15) . . ?
C24 C25 H25 121.1 . . ?
C4 C25 H25 121.1 . . ?
C30 C31 C26 120.70(13) . . ?
C30 C31 H31 119.7 . . ?
C26 C31 H31 119.7 . . ?
C28 C27 C26 120.92(14) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C19 C18 C17 119.88(14) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C9 C10 C11 120.05(14) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C11 C12 C13 121.56(14) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C3 C4 C25 121.99(13) . . ?
C3 C4 C5 109.81(12) . . ?
C25 C4 C5 128.10(13) . . ?
C12 C11 C10 119.19(14) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C31 C26 C27 118.20(13) . . ?
C31 C26 C14 121.01(12) . . ?
C27 C26 C14 120.78(12) . . ?
C25 C24 C23 120.40(15) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C29 C30 C31 120.57(14) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C27 C28 C29 120.15(13) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C20 C19 C18 119.75(13) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C30 C29 C28 119.45(14) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C22 C23 C24 121.65(14) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
O15 C14 C1 58.83(8) . . ?
O15 C14 C26 114.09(10) . . ?
C1 C14 C26 121.76(12) . . ?
O15 C14 C13 115.19(11) . . ?
C1 C14 C13 118.58(11) . . ?
C26 C14 C13 115.33(11) . . ?
C6 C7 C8 121.30(11) . . ?
C6 C7 C16 121.41(12) . . ?
C8 C7 C16 116.36(11) . . ?

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
C21 C16 C17 C18 0.1(2) . . . . ?
C7 C16 C17 C18 -176.17(13) . . . . ?
O32 C5 C6 C7 -13.8(2) . . . . ?
C4 C5 C6 C7 169.35(12) . . . . ?
O32 C5 C6 C2 169.30(13) . . . . ?
C4 C5 C6 C2 -7.56(13) . . . . ?
C3 C2 C6 C7 -170.97(12) . . . . ?
C1 C2 C6 C7 66.13(16) . . . . ?
C3 C2 C6 C5 6.05(13) . . . . ?
C1 C2 C6 C5 -116.86(12) . . . . ?
C17 C16 C21 C20 1.2(2) . . . . ?
C7 C16 C21 C20 177.36(13) . . . . ?
C19 C20 C21 C16 -1.6(2) . . . . ?
C1 C2 C3 C4 116.48(12) . . . . ?
C6 C2 C3 C4 -2.27(14) . . . . ?
C1 C2 C3 C22 -61.48(18) . . . . ?
C6 C2 C3 C22 179.76(13) . . . . ?
C14 O15 C1 C2 108.11(13) . . . . ?
C3 C2 C1 O15 107.83(13) . . . . ?
C6 C2 C1 O15 -136.48(11) . . . . ?
C3 C2 C1 C14 177.02(11) . . . . ?
C6 C2 C1 C14 -67.29(15) . . . . ?
C10 C9 C8 C13 5.7(2) . . . . ?
C10 C9 C8 C7 -169.01(13) . . . . ?
C4 C3 C22 C23 -0.2(2) . . . . ?
C2 C3 C22 C23 177.62(13) . . . . ?
C9 C8 C13 C12 -6.91(19) . . . . ?
C7 C8 C13 C12 167.35(13) . . . . ?
C9 C8 C13 C14 166.45(12) . . . . ?
C7 C8 C13 C14 -19.3(2) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C8 C13 C12 C11 2.7(2) . . . . ?
C14 C13 C12 C11 -170.95(13) . . . . ?
C22 C3 C4 C25 -1.0(2) . . . . ?
C2 C3 C4 C25 -179.12(12) . . . . ?
C22 C3 C4 C5 175.73(12) . . . . ?
C2 C3 C4 C5 -2.43(15) . . . . ?
C24 C25 C4 C3 1.0(2) . . . . ?
C24 C25 C4 C5 -175.08(13) . . . . ?
O32 C5 C4 C3 -170.77(13) . . . . ?
C6 C5 C4 C3 6.21(14) . . . . ?
O32 C5 C4 C25 5.7(2) . . . . ?
C6 C5 C4 C25 -177.36(13) . . . . ?
C13 C12 C11 C10 3.1(2) . . . . ?
C9 C10 C11 C12 -4.4(2) . . . . ?
C30 C31 C26 C27 0.8(2) . . . . ?
C30 C31 C26 C14 -178.20(13) . . . . ?
C28 C27 C26 C31 -0.7(2) . . . . ?
C28 C27 C26 C14 178.29(13) . . . . ?
C4 C25 C24 C23 0.2(2) . . . . ?
C26 C31 C30 C29 -0.1(2) . . . . ?
C26 C27 C28 C29 -0.1(2) . . . . ?
C21 C20 C19 C18 0.6(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C31 C30 C29 C28 -0.8(2) . . . . ?
C27 C28 C29 C30 0.9(2) . . . . ?
C3 C22 C23 C24 1.3(2) . . . . ?
C25 C24 C23 C22 -1.3(2) . . . . ?
C1 O15 C14 C26 113.79(13) . . . . ?
C1 O15 C14 C13 -109.47(13) . . . . ?
C2 C1 C14 O15 -107.18(13) . . . . ?
O15 C1 C14 C26 -100.76(13) . . . . ?
C2 C1 C14 C26 152.06(11) . . . . ?
O15 C1 C14 C13 103.71(12) . . . . ?
C2 C1 C14 C13 -3.47(17) . . . . ?
C31 C26 C14 O15 154.39(12) . . . . ?
C27 C26 C14 O15 -24.58(17) . . . . ?
C31 C26 C14 C1 -138.56(13) . . . . ?
C27 C26 C14 C1 42.47(18) . . . . ?
C31 C26 C14 C13 17.71(17) . . . . ?
C27 C26 C14 C13 -161.26(12) . . . . ?
C12 C13 C14 O15 -63.60(16) . . . . ?
C8 C13 C14 O15 122.95(13) . . . . ?
C12 C13 C14 C1 -130.33(13) . . . . ?
C8 C13 C14 C1 56.22(17) . . . . ?
C12 C13 C14 C26 72.60(15) . . . . ?
C8 C13 C14 C26 -100.85(15) . . . . ?
C5 C6 C7 C8 -173.15(12) . . . . ?
C2 C6 C7 C8 3.30(19) . . . . ?
C5 C6 C7 C16 -4.6(2) . . . . ?
C2 C6 C7 C16 171.90(12) . . . . ?
C9 C8 C7 C6 141.55(13) . . . . ?
C13 C8 C7 C6 -32.73(19) . . . . ?
C9 C8 C7 C16 -27.60(17) . . . . ?
C13 C8 C7 C16 158.12(12) . . . . ?
C21 C16 C7 C6 117.57(15) . . . . ?
C17 C16 C7 C6 -66.30(17) . . . . ?
C21 C16 C7 C8 -73.30(16) . . . . ?
C17 C16 C7 C8 102.83(14) . . . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040

