# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
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data_20211227c
_database_code_depnum_ccdc_archive 'CCDC 2160295'
loop_
_audit_author_name
_audit_author_address
'Shaoyin Wang'
;Wannan Medical College
China
;
_audit_update_record             
;
2022-03-20 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H23 N O2'
_chemical_formula_sum            'C31 H23 N O2'
_chemical_formula_weight         441.50
_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'
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'

_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                   10.1008(11)
_cell_length_b                   23.219(3)
_cell_length_c                   10.2424(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.434(4)
_cell_angle_gamma                90
_cell_volume                     2278.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    300
_cell_measurement_theta_max      29.804
_cell_measurement_theta_min      2.632
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0679 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.9298.
The λ/2 correction factor is Not present.
;
_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    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            83541
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.935
_diffrn_reflns_theta_min         2.620
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4711
_reflns_number_total             6610
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0165(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.024
_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)+(0.0523P)²+0.5583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85462(14) 0.23949(4) 0.55646(11) 0.0604(3) Uani 1 1 d . . . . .
O2 O 0.74009(9) 0.43744(3) 0.48814(8) 0.0356(2) Uani 1 1 d . . . . .
N1 N 0.89882(12) 0.29930(5) 0.74138(11) 0.0392(2) Uani 1 1 d . . . . .
C1 C 0.96943(18) 0.25185(7) 0.83125(16) 0.0559(4) Uani 1 1 d . . . . .
H1A H 1.055603 0.265476 0.894598 0.084 Uiso 1 1 calc R U . . .
H1B H 0.988314 0.221357 0.776347 0.084 Uiso 1 1 calc R U . . .
H1C H 0.910550 0.237673 0.881578 0.084 Uiso 1 1 calc R U . . .
C2 C 0.87844(12) 0.35147(5) 0.79853(12) 0.0351(3) Uani 1 1 d . . . . .
C3 C 0.91415(14) 0.35910(7) 0.94151(13) 0.0453(3) Uani 1 1 d . . . . .
H3 H 0.952297 0.328694 1.000505 0.054 Uiso 1 1 calc R U . . .
C4 C 0.89285(16) 0.41140(7) 0.99447(14) 0.0510(4) Uani 1 1 d . . . . .
H4 H 0.916861 0.415806 1.089371 0.061 Uiso 1 1 calc R U . . .
C5 C 0.83635(16) 0.45783(7) 0.90970(14) 0.0497(3) Uani 1 1 d . . . . .
H5 H 0.823788 0.493060 0.947361 0.060 Uiso 1 1 calc R U . . .
C6 C 0.79911(14) 0.45102(6) 0.76901(13) 0.0407(3) Uani 1 1 d . . . . .
H6 H 0.760151 0.481765 0.711483 0.049 Uiso 1 1 calc R U . . .
C7 C 0.81939(12) 0.39823(5) 0.71184(12) 0.0329(2) Uani 1 1 d . . . . .
C8 C 0.78597(12) 0.38980(5) 0.56600(11) 0.0314(2) Uani 1 1 d . . . . .
C9 C 0.80688(12) 0.33857(5) 0.51060(12) 0.0337(3) Uani 1 1 d . . . . .
C10 C 0.85285(14) 0.28856(5) 0.60014(13) 0.0397(3) Uani 1 1 d . . . . .
C11 C 0.78721(12) 0.33645(5) 0.36228(12) 0.0332(2) Uani 1 1 d . . . . .
C12 C 0.71863(13) 0.37999(5) 0.28435(12) 0.0360(3) Uani 1 1 d . . . . .
H12 H 0.709187 0.380416 0.191038 0.043 Uiso 1 1 calc R U . . .
C13 C 0.65587(12) 0.42866(5) 0.34404(11) 0.0328(2) Uani 1 1 d . . . . .
C14 C 0.85428(13) 0.29088(5) 0.30234(12) 0.0339(3) Uani 1 1 d . . . . .
C15 C 0.77916(14) 0.26043(6) 0.18577(14) 0.0424(3) Uani 1 1 d . . . . .
H15 H 0.684556 0.267817 0.144845 0.051 Uiso 1 1 calc R U . . .
C16 C 0.84457(16) 0.21909(6) 0.13018(15) 0.0486(3) Uani 1 1 d . . . . .
H16 H 0.793188 0.198551 0.052785 0.058 Uiso 1 1 calc R U . . .
C17 C 0.98438(16) 0.20818(6) 0.18823(16) 0.0503(3) Uani 1 1 d . . . . .
H17 H 1.027668 0.180473 0.150152 0.060 Uiso 1 1 calc R U . . .
C18 C 1.06030(16) 0.23838(7) 0.30297(17) 0.0545(4) Uani 1 1 d . . . . .
H18 H 1.155263 0.231317 0.342277 0.065 Uiso 1 1 calc R U . . .
C19 C 0.99541(14) 0.27925(6) 0.35990(15) 0.0451(3) Uani 1 1 d . . . . .
H19 H 1.047257 0.299248 0.438015 0.054 Uiso 1 1 calc R U . . .
C20 C 0.50619(12) 0.41478(5) 0.33805(12) 0.0332(2) Uani 1 1 d . . . . .
C21 C 0.41404(15) 0.39268(6) 0.21754(14) 0.0471(3) Uani 1 1 d . . . . .
H21 H 0.445361 0.385019 0.143144 0.056 Uiso 1 1 calc R U . . .
C22 C 0.27674(16) 0.38194(7) 0.20662(17) 0.0557(4) Uani 1 1 d . . . . .
H22 H 0.216109 0.367487 0.124835 0.067 Uiso 1 1 calc R U . . .
C23 C 0.22886(15) 0.39252(6) 0.31627(17) 0.0517(4) Uani 1 1 d . . . . .
H23 H 0.136136 0.385360 0.308707 0.062 Uiso 1 1 calc R U . . .
C24 C 0.31955(15) 0.41381(6) 0.43735(16) 0.0479(3) Uani 1 1 d . . . . .
H24 H 0.288107 0.420578 0.512071 0.058 Uiso 1 1 calc R U . . .
C25 C 0.45724(14) 0.42515(6) 0.44812(13) 0.0397(3) Uani 1 1 d . . . . .
H25 H 0.517428 0.439848 0.529854 0.048 Uiso 1 1 calc R U . . .
C26 C 0.66862(13) 0.48599(5) 0.27566(12) 0.0345(3) Uani 1 1 d . . . . .
C27 C 0.55459(15) 0.51942(6) 0.20793(14) 0.0456(3) Uani 1 1 d . . . . .
H27 H 0.465322 0.506234 0.199500 0.055 Uiso 1 1 calc R U . . .
C28 C 0.57106(19) 0.57253(7) 0.15205(17) 0.0585(4) Uani 1 1 d . . . . .
H28 H 0.492978 0.594583 0.107489 0.070 Uiso 1 1 calc R U . . .
C29 C 0.7007(2) 0.59242(7) 0.16218(17) 0.0622(4) Uani 1 1 d . . . . .
H29 H 0.711808 0.628092 0.125639 0.075 Uiso 1 1 calc R U . . .
C30 C 0.8151(2) 0.55909(8) 0.2272(2) 0.0686(5) Uani 1 1 d . . . . .
H30 H 0.903830 0.572184 0.233169 0.082 Uiso 1 1 calc R U . . .
C31 C 0.80006(16) 0.50628(7) 0.28378(17) 0.0546(4) Uani 1 1 d . . . . .
H31 H 0.878578 0.484316 0.327478 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.2261(16) . ?
O2 C8 1.3568(14) . ?
O2 C13 1.4661(13) . ?
N1 C1 1.4679(17) . ?
N1 C2 1.3887(16) . ?
N1 C10 1.3949(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.4043(17) . ?
C2 C7 1.4100(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3785(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.4011(18) . ?
C7 C8 1.4369(16) . ?
C8 C9 1.3628(16) . ?
C9 C10 1.4613(17) . ?
C9 C11 1.4693(16) . ?
C11 C12 1.3377(17) . ?
C11 C14 1.4896(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.5158(16) . ?
C13 C20 1.5280(17) . ?
C13 C26 1.5284(17) . ?
C14 C15 1.3885(17) . ?
C14 C19 1.3860(18) . ?
C15 H15 0.9300 . ?
C15 C16 1.3857(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.3880(18) . ?
C20 C25 1.3878(17) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.3853(19) . ?
C25 H25 0.9300 . ?
C26 C27 1.3803(18) . ?
C26 C31 1.3862(19) . ?
C27 H27 0.9300 . ?
C27 C28 1.391(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.362(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.375(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.385(2) . ?
C31 H31 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
C8 O2 C13 117.38(9) . . ?
C2 N1 C1 119.86(11) . . ?
C2 N1 C10 123.22(10) . . ?
C10 N1 C1 116.91(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.75(11) . . ?
N1 C2 C7 119.73(11) . . ?
C3 C2 C7 118.52(12) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.16(13) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.59(13) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.14(13) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.63(13) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C8 117.59(11) . . ?
C6 C7 C2 119.94(11) . . ?
C6 C7 C8 122.44(11) . . ?
O2 C8 C7 115.10(10) . . ?
O2 C8 C9 122.41(10) . . ?
C9 C8 C7 122.37(11) . . ?
C8 C9 C10 119.50(11) . . ?
C8 C9 C11 118.14(11) . . ?
C10 C9 C11 122.32(11) . . ?
O1 C10 N1 120.40(12) . . ?
O1 C10 C9 123.21(12) . . ?
N1 C10 C9 116.38(11) . . ?
C9 C11 C14 121.30(10) . . ?
C12 C11 C9 117.84(11) . . ?
C12 C11 C14 120.54(11) . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.76(11) . . ?
C13 C12 H12 119.1 . . ?
O2 C13 C12 109.04(9) . . ?
O2 C13 C20 108.76(9) . . ?
O2 C13 C26 103.54(9) . . ?
C12 C13 C20 111.17(10) . . ?
C12 C13 C26 110.97(10) . . ?
C20 C13 C26 113.01(10) . . ?
C15 C14 C11 121.33(11) . . ?
C19 C14 C11 120.24(11) . . ?
C19 C14 C15 118.40(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.27(12) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.61(13) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.72(13) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.99(14) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.01(13) . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C13 119.37(11) . . ?
C25 C20 C13 122.20(11) . . ?
C25 C20 C21 118.39(12) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.91(14) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.33(14) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.48(13) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.28(13) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.59(13) . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C13 122.83(11) . . ?
C27 C26 C31 118.05(12) . . ?
C31 C26 C13 119.10(12) . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 121.05(14) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.44(15) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.4 . . ?
C28 C29 C30 119.12(15) . . ?
C30 C29 H29 120.4 . . ?
C29 C30 H30 119.5 . . ?
C29 C30 C31 120.97(16) . . ?
C31 C30 H30 119.5 . . ?
C26 C31 H31 119.8 . . ?
C30 C31 C26 120.36(15) . . ?
C30 C31 H31 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 C8 C9 C10 -178.35(11) . . . . ?
O2 C8 C9 C11 3.99(17) . . . . ?
O2 C13 C20 C21 -166.20(11) . . . . ?
O2 C13 C20 C25 15.80(15) . . . . ?
O2 C13 C26 C27 -121.53(12) . . . . ?
O2 C13 C26 C31 57.11(14) . . . . ?
N1 C2 C3 C4 179.83(12) . . . . ?
N1 C2 C7 C6 -179.76(11) . . . . ?
N1 C2 C7 C8 -1.60(17) . . . . ?
C1 N1 C2 C3 -4.92(19) . . . . ?
C1 N1 C2 C7 175.60(12) . . . . ?
C1 N1 C10 O1 9.8(2) . . . . ?
C1 N1 C10 C9 -168.84(12) . . . . ?
C2 N1 C10 O1 -168.98(13) . . . . ?
C2 N1 C10 C9 12.35(18) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C7 C8 O2 -174.88(10) . . . . ?
C2 C7 C8 C9 1.31(17) . . . . ?
C3 C2 C7 C6 0.75(18) . . . . ?
C3 C2 C7 C8 178.90(11) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C2 -0.02(19) . . . . ?
C5 C6 C7 C8 -178.08(12) . . . . ?
C6 C7 C8 O2 3.22(17) . . . . ?
C6 C7 C8 C9 179.42(12) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C7 C8 C9 C10 5.73(18) . . . . ?
C7 C8 C9 C11 -171.93(10) . . . . ?
C8 O2 C13 C12 -41.42(13) . . . . ?
C8 O2 C13 C20 79.96(12) . . . . ?
C8 O2 C13 C26 -159.61(9) . . . . ?
C8 C9 C10 O1 169.18(13) . . . . ?
C8 C9 C10 N1 -12.19(18) . . . . ?
C8 C9 C11 C12 -15.75(17) . . . . ?
C8 C9 C11 C14 157.73(11) . . . . ?
C9 C11 C12 C13 -3.20(18) . . . . ?
C9 C11 C14 C15 132.63(13) . . . . ?
C9 C11 C14 C19 -49.49(17) . . . . ?
C10 N1 C2 C3 173.85(12) . . . . ?
C10 N1 C2 C7 -5.63(18) . . . . ?
C10 C9 C11 C12 166.66(12) . . . . ?
C10 C9 C11 C14 -19.87(18) . . . . ?
C11 C9 C10 O1 -13.3(2) . . . . ?
C11 C9 C10 N1 165.37(11) . . . . ?
C11 C12 C13 O2 30.36(16) . . . . ?
C11 C12 C13 C20 -89.54(14) . . . . ?
C11 C12 C13 C26 143.78(12) . . . . ?
C11 C14 C15 C16 178.60(12) . . . . ?
C11 C14 C19 C18 -177.92(13) . . . . ?
C12 C11 C14 C15 -54.07(18) . . . . ?
C12 C11 C14 C19 123.81(14) . . . . ?
C12 C13 C20 C21 -46.14(15) . . . . ?
C12 C13 C20 C25 135.87(12) . . . . ?
C12 C13 C26 C27 121.62(13) . . . . ?
C12 C13 C26 C31 -59.73(15) . . . . ?
C13 O2 C8 C7 -157.17(10) . . . . ?
C13 O2 C8 C9 26.63(16) . . . . ?
C13 C20 C21 C22 -177.26(13) . . . . ?
C13 C20 C25 C24 177.82(12) . . . . ?
C13 C26 C27 C28 177.24(13) . . . . ?
C13 C26 C31 C30 -177.63(14) . . . . ?
C14 C11 C12 C13 -176.72(11) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C14 C19 C18 0.0(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C14 -0.6(2) . . . . ?
C19 C14 C15 C16 0.7(2) . . . . ?
C20 C13 C26 C27 -4.04(16) . . . . ?
C20 C13 C26 C31 174.60(12) . . . . ?
C20 C21 C22 C23 -0.6(2) . . . . ?
C21 C20 C25 C24 -0.19(19) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
C22 C23 C24 C25 0.8(2) . . . . ?
C23 C24 C25 C20 -0.6(2) . . . . ?
C25 C20 C21 C22 0.8(2) . . . . ?
C26 C13 C20 C21 79.42(14) . . . . ?
C26 C13 C20 C25 -98.58(13) . . . . ?
C26 C27 C28 C29 0.6(2) . . . . ?
C27 C26 C31 C30 1.1(2) . . . . ?
C27 C28 C29 C30 0.6(3) . . . . ?
C28 C29 C30 C31 -1.0(3) . . . . ?
C29 C30 C31 C26 0.1(3) . . . . ?
C31 C26 C27 C28 -1.4(2) . . . . ?

_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_20220105b
_database_code_depnum_ccdc_archive 'CCDC 2160296'
loop_
_audit_author_name
_audit_author_address
'Shaoyin Wang'
;Wannan Medical College
China
;
_audit_update_record             
;
2022-03-20 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 Cl N O2'
_chemical_formula_sum            'C25 H18 Cl N O2'
_chemical_formula_weight         399.85
_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'
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'

_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                   7.3410(14)
_cell_length_b                   15.791(3)
_cell_length_c                   17.132(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.737(7)
_cell_angle_gamma                90
_cell_volume                     1979.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9554
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      24.442
_cell_measurement_theta_min      2.580
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1170 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.7929.
The λ/2 correction factor is Not present.
;
_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    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1629
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_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       -22
_diffrn_reflns_number            61242
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.025
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2504
_reflns_number_total             4747
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.026
_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)+(0.0898P)²+0.8634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.2056
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.07457(14) 1.06533(7) 0.09495(5) 0.0886(4) Uani 1 1 d . . . . .
O1 O 0.4830(4) 0.81728(15) 0.69297(14) 0.0838(8) Uani 1 1 d . . . . .
O2 O 0.2422(3) 0.97325(12) 0.47935(11) 0.0534(5) Uani 1 1 d . . . . .
N1 N 0.4325(3) 0.95950(16) 0.71107(14) 0.0561(6) Uani 1 1 d . . . . .
C1 C 0.4281(4) 0.8856(2) 0.66583(19) 0.0592(8) Uani 1 1 d . . . . .
C2 C 0.3547(4) 0.89671(18) 0.58535(17) 0.0525(7) Uani 1 1 d . . . . .
C3 C 0.3052(4) 0.97354(17) 0.55749(16) 0.0479(7) Uani 1 1 d . . . . .
C4 C 0.3149(4) 1.04933(17) 0.60211(16) 0.0482(7) Uani 1 1 d . . . . .
C5 C 0.3808(4) 1.03944(19) 0.68196(17) 0.0504(7) Uani 1 1 d . . . . .
C6 C 0.3902(4) 1.1118(2) 0.72935(19) 0.0625(8) Uani 1 1 d . . . . .
H6 H 0.432300 1.107339 0.781893 0.075 Uiso 1 1 calc R U . . .
C7 C 0.3379(5) 1.1891(2) 0.6990(2) 0.0700(9) Uani 1 1 d . . . . .
H7 H 0.345933 1.236490 0.731396 0.084 Uiso 1 1 calc R U . . .
C8 C 0.2730(5) 1.1985(2) 0.6207(2) 0.0663(9) Uani 1 1 d . . . . .
H8 H 0.236914 1.251421 0.601137 0.080 Uiso 1 1 calc R U . . .
C9 C 0.2631(4) 1.12898(18) 0.57299(18) 0.0546(7) Uani 1 1 d . . . . .
H9 H 0.221253 1.134861 0.520536 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4948(5) 0.9498(2) 0.79477(19) 0.0736(10) Uani 1 1 d . . . . .
H10A H 0.603471 0.982735 0.806550 0.110 Uiso 1 1 calc R U . . .
H10B H 0.520513 0.891235 0.805920 0.110 Uiso 1 1 calc R U . . .
H10C H 0.400750 0.969126 0.826242 0.110 Uiso 1 1 calc R U . . .
C11 C 0.3210(4) 0.83116(17) 0.52201(17) 0.0520(7) Uani 1 1 d . . . . .
H11 H 0.436827 0.804819 0.510695 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1812(4) 0.76277(16) 0.53785(16) 0.0488(7) Uani 1 1 d . . . . .
C13 C 0.0363(4) 0.77935(19) 0.58259(17) 0.0574(8) Uani 1 1 d . . . . .
H13 H 0.028960 0.831778 0.606868 0.069 Uiso 1 1 calc R U . . .
C14 C -0.0986(5) 0.7190(2) 0.59184(19) 0.0706(9) Uani 1 1 d . . . . .
H14 H -0.195669 0.731320 0.621557 0.085 Uiso 1 1 calc R U . . .
C15 C -0.0875(6) 0.6414(2) 0.5570(2) 0.0814(12) Uani 1 1 d . . . . .
H15 H -0.177362 0.600917 0.562760 0.098 Uiso 1 1 calc R U . . .
C16 C 0.0571(7) 0.6234(2) 0.5133(2) 0.0864(12) Uani 1 1 d . . . . .
H16 H 0.065016 0.570366 0.490252 0.104 Uiso 1 1 calc R U . . .
C17 C 0.1908(5) 0.6836(2) 0.5035(2) 0.0714(9) Uani 1 1 d . . . . .
H17 H 0.287474 0.670722 0.473734 0.086 Uiso 1 1 calc R U . . .
C18 C 0.2504(4) 0.88870(17) 0.45328(17) 0.0509(7) Uani 1 1 d . . . . .
C19 C 0.2017(4) 0.86735(19) 0.37996(17) 0.0534(7) Uani 1 1 d . . . . .
H19 H 0.213049 0.809995 0.369020 0.064 Uiso 1 1 calc R U . . .
C20 C 0.1325(4) 0.91928(18) 0.31303(16) 0.0494(7) Uani 1 1 d . . . . .
C21 C 0.0800(4) 0.8782(2) 0.24222(18) 0.0602(8) Uani 1 1 d . . . . .
H21 H 0.089099 0.819537 0.239729 0.072 Uiso 1 1 calc R U . . .
C22 C 0.0150(4) 0.9222(2) 0.17603(18) 0.0645(9) Uani 1 1 d . . . . .
H22 H -0.019248 0.893491 0.129740 0.077 Uiso 1 1 calc R U . . .
C23 C 0.0016(4) 1.0089(2) 0.17934(17) 0.0595(8) Uani 1 1 d . . . . .
C24 C 0.0503(5) 1.0520(2) 0.24783(18) 0.0621(8) Uani 1 1 d . . . . .
H24 H 0.040029 1.110653 0.249488 0.075 Uiso 1 1 calc R U . . .
C25 C 0.1152(4) 1.0073(2) 0.31467(17) 0.0576(8) Uani 1 1 d . . . . .
H25 H 0.147202 1.036539 0.360915 0.069 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C23 1.750(3) . ?
O1 C1 1.229(4) . ?
O2 C3 1.380(3) . ?
O2 C18 1.411(3) . ?
N1 C1 1.400(4) . ?
N1 C5 1.398(4) . ?
N1 C10 1.476(4) . ?
C1 C2 1.449(4) . ?
C2 C3 1.343(4) . ?
C2 C11 1.505(4) . ?
C3 C4 1.419(4) . ?
C4 C5 1.422(4) . ?
C4 C9 1.394(4) . ?
C5 C6 1.400(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.369(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9800 . ?
C11 C12 1.530(4) . ?
C11 C18 1.543(4) . ?
C12 C13 1.387(4) . ?
C12 C17 1.386(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.321(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.466(4) . ?
C20 C21 1.402(4) . ?
C20 C25 1.397(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(5) . ?
C23 C24 1.378(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.395(4) . ?
C25 H25 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
C3 O2 C18 106.9(2) . . ?
C1 N1 C10 116.3(3) . . ?
C5 N1 C1 124.2(2) . . ?
C5 N1 C10 119.5(3) . . ?
O1 C1 N1 122.0(3) . . ?
O1 C1 C2 123.4(3) . . ?
N1 C1 C2 114.6(3) . . ?
C1 C2 C11 128.9(3) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 C11 110.0(2) . . ?
O2 C3 C4 121.6(2) . . ?
C2 C3 O2 113.6(2) . . ?
C2 C3 C4 124.8(3) . . ?
C3 C4 C5 115.1(2) . . ?
C9 C4 C3 124.6(3) . . ?
C9 C4 C5 120.3(3) . . ?
N1 C5 C4 120.2(3) . . ?
N1 C5 C6 122.1(3) . . ?
C6 C5 C4 117.7(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.5(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11 110.0 . . ?
C2 C11 C12 115.5(2) . . ?
C2 C11 C18 99.8(2) . . ?
C12 C11 H11 110.0 . . ?
C12 C11 C18 111.3(2) . . ?
C18 C11 H11 110.0 . . ?
C13 C12 C11 121.4(3) . . ?
C17 C12 C11 120.2(3) . . ?
C17 C12 C13 118.2(3) . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.4(4) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O2 C18 C11 109.6(2) . . ?
C19 C18 O2 121.8(3) . . ?
C19 C18 C11 128.5(3) . . ?
C18 C19 H19 114.7 . . ?
C18 C19 C20 130.5(3) . . ?
C20 C19 H19 114.7 . . ?
C21 C20 C19 118.1(3) . . ?
C25 C20 C19 124.6(3) . . ?
C25 C20 C21 117.3(3) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 C20 122.0(3) . . ?
C22 C21 H21 119.0 . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 Cl1 119.5(2) . . ?
C22 C23 C24 120.8(3) . . ?
C24 C23 Cl1 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.8(3) . . ?
C24 C25 H25 119.6 . . ?

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 C23 C24 C25 -178.5(2) . . . . ?
O1 C1 C2 C3 -176.5(3) . . . . ?
O1 C1 C2 C11 3.6(5) . . . . ?
O2 C3 C4 C5 179.4(2) . . . . ?
O2 C3 C4 C9 0.2(4) . . . . ?
O2 C18 C19 C20 -0.3(5) . . . . ?
N1 C1 C2 C3 3.3(4) . . . . ?
N1 C1 C2 C11 -176.6(3) . . . . ?
N1 C5 C6 C7 -179.8(3) . . . . ?
C1 N1 C5 C4 1.4(4) . . . . ?
C1 N1 C5 C6 -179.0(3) . . . . ?
C1 C2 C3 O2 178.5(2) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C1 C2 C11 C12 62.7(4) . . . . ?
C1 C2 C11 C18 -178.0(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C9 -179.9(3) . . . . ?
C2 C11 C12 C13 30.3(4) . . . . ?
C2 C11 C12 C17 -153.6(3) . . . . ?
C2 C11 C18 O2 -2.1(3) . . . . ?
C2 C11 C18 C19 178.2(3) . . . . ?
C3 O2 C18 C11 1.3(3) . . . . ?
C3 O2 C18 C19 -178.9(3) . . . . ?
C3 C2 C11 C12 -117.2(3) . . . . ?
C3 C2 C11 C18 2.1(3) . . . . ?
C3 C4 C5 N1 0.7(4) . . . . ?
C3 C4 C5 C6 -178.8(2) . . . . ?
C3 C4 C9 C8 178.5(3) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 N1 C1 O1 176.5(3) . . . . ?
C5 N1 C1 C2 -3.4(4) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C4 0.8(5) . . . . ?
C9 C4 C5 N1 179.9(3) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
C10 N1 C1 O1 -4.1(4) . . . . ?
C10 N1 C1 C2 176.0(3) . . . . ?
C10 N1 C5 C4 -177.9(3) . . . . ?
C10 N1 C5 C6 1.6(4) . . . . ?
C11 C2 C3 O2 -1.5(3) . . . . ?
C11 C2 C3 C4 178.5(3) . . . . ?
C11 C12 C13 C14 175.0(3) . . . . ?
C11 C12 C17 C16 -175.5(3) . . . . ?
C11 C18 C19 C20 179.4(3) . . . . ?
C12 C11 C18 O2 120.3(3) . . . . ?
C12 C11 C18 C19 -59.4(4) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C13 C12 C17 C16 0.7(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.8(6) . . . . ?
C15 C16 C17 C12 0.3(6) . . . . ?
C17 C12 C13 C14 -1.2(4) . . . . ?
C18 O2 C3 C2 0.1(3) . . . . ?
C18 O2 C3 C4 -180.0(2) . . . . ?
C18 C11 C12 C13 -82.5(3) . . . . ?
C18 C11 C12 C17 93.6(3) . . . . ?
C18 C19 C20 C21 -175.9(3) . . . . ?
C18 C19 C20 C25 4.1(5) . . . . ?
C19 C20 C21 C22 -179.4(3) . . . . ?
C19 C20 C25 C24 179.1(3) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C20 C25 C24 -0.9(4) . . . . ?
C21 C22 C23 Cl1 178.2(2) . . . . ?
C21 C22 C23 C24 -0.6(5) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C23 C24 C25 C20 0.4(5) . . . . ?
C25 C20 C21 C22 0.6(4) . . . . ?

_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_211106d_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2168808'
loop_
_audit_author_name
_audit_author_address
'Shaoyin Wang'
;Wannan Medical College
China
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H27 N O'
_chemical_formula_sum            'C39 H27 N O'
_chemical_formula_weight         525.61
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.696(3)
_cell_length_b                   12.279(4)
_cell_length_c                   13.367(4)
_cell_angle_alpha                69.289(3)
_cell_angle_beta                 74.425(3)
_cell_angle_gamma                68.877(3)
_cell_volume                     1370.3(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8540
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1136 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.8317.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.581
_diffrn_reflns_theta_min         1.650
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5122
_reflns_number_total             6244
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C33(H33), C13(H13), C21(H21), C27(H27), C17(H17), C29(H29), C35(H35),
 C39(H39), C20(H20), C23(H23), C32(H32), C8(H8), C19(H19), C6(H6), C36(H36),
 C30(H30), C26(H26), C18(H18), C38(H38), C7(H7), C24(H24), C31(H31), C25(H25),
 C37(H37)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93841(12) 0.22070(9) 0.63503(9) 0.0591(3) Uani 1 1 d . . . . .
N1 N 0.80707(13) 0.39113(11) 0.52228(9) 0.0462(3) Uani 1 1 d . . . . .
C28 C 0.66773(13) 0.61080(10) 0.92977(9) 0.0321(2) Uani 1 1 d . . . . .
C16 C 0.40245(13) 0.73905(11) 0.72923(9) 0.0351(3) Uani 1 1 d . . . . .
C12 C 0.72047(12) 0.54670(10) 0.84418(9) 0.0316(2) Uani 1 1 d . . . . .
C11 C 0.67259(12) 0.58994(10) 0.74434(9) 0.0330(2) Uani 1 1 d . . . . .
C3 C 0.73318(13) 0.51272(11) 0.67724(9) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.89076(13) 0.35613(10) 0.79780(10) 0.0336(3) Uani 1 1 d . . . . .
C33 C 0.51752(14) 0.64604(11) 0.97502(10) 0.0372(3) Uani 1 1 d . . . . .
H33 H 0.446642 0.630828 0.950923 0.045 Uiso 1 1 calc R U . . .
C22 C 0.63748(13) 0.81481(11) 0.66505(10) 0.0391(3) Uani 1 1 d . . . . .
C2 C 0.83476(13) 0.39714(11) 0.69920(10) 0.0351(3) Uani 1 1 d . . . . .
C4 C 0.67534(14) 0.56879(12) 0.57880(10) 0.0388(3) Uani 1 1 d . . . . .
C13 C 0.83104(13) 0.43200(11) 0.86549(9) 0.0338(3) Uani 1 1 d . . . . .
H13 H 0.867173 0.404741 0.930577 0.041 Uiso 1 1 calc R U . . .
C34 C 1.01261(13) 0.24239(11) 0.83336(10) 0.0364(3) Uani 1 1 d . . . . .
C21 C 0.34041(14) 0.64358(12) 0.78380(10) 0.0400(3) Uani 1 1 d . . . . .
H21 H 0.402551 0.563721 0.798827 0.048 Uiso 1 1 calc R U . . .
C10 C 0.56987(13) 0.71278(11) 0.68123(9) 0.0353(3) Uani 1 1 d . . . . .
C9 C 0.58206(14) 0.68519(12) 0.57388(10) 0.0394(3) Uani 1 1 d . . . . .
C27 C 0.60769(15) 0.87017(12) 0.74628(11) 0.0444(3) Uani 1 1 d . . . . .
H27 H 0.539663 0.849938 0.808437 0.053 Uiso 1 1 calc R U . . .
C1 C 0.86621(14) 0.32810(12) 0.61917(11) 0.0422(3) Uani 1 1 d . . . . .
C5 C 0.70946(14) 0.50990(13) 0.50024(10) 0.0423(3) Uani 1 1 d . . . . .
C17 C 0.30663(14) 0.85712(12) 0.70732(11) 0.0446(3) Uani 1 1 d . . . . .
H17 H 0.345856 0.922065 0.669985 0.054 Uiso 1 1 calc R U . . .
C29 C 0.77167(15) 0.63196(12) 0.96963(11) 0.0434(3) Uani 1 1 d . . . . .
H29 H 0.872953 0.607328 0.941583 0.052 Uiso 1 1 calc R U . . .
C35 C 1.14577(14) 0.21139(12) 0.76253(12) 0.0438(3) Uani 1 1 d . . . . .
H35 H 1.154863 0.257621 0.690299 0.053 Uiso 1 1 calc R U . . .
C39 C 1.00249(16) 0.17166(12) 0.94037(12) 0.0453(3) Uani 1 1 d . . . . .
H39 H 0.914400 0.190451 0.988532 0.054 Uiso 1 1 calc R U . . .
C20 C 0.18692(15) 0.66639(14) 0.81596(11) 0.0478(3) Uani 1 1 d . . . . .
H20 H 0.146959 0.601749 0.852586 0.057 Uiso 1 1 calc R U . . .
C23 C 0.73800(15) 0.84917(14) 0.57260(12) 0.0511(3) Uani 1 1 d . . . . .
H23 H 0.759088 0.814504 0.516546 0.061 Uiso 1 1 calc R U . . .
C32 C 0.47249(15) 0.70371(13) 1.05586(11) 0.0454(3) Uani 1 1 d . . . . .
H32 H 0.371618 0.727497 1.085212 0.054 Uiso 1 1 calc R U . . .
C8 C 0.51244(16) 0.74989(14) 0.48381(11) 0.0492(3) Uani 1 1 d . . . . .
H8 H 0.448566 0.828795 0.476494 0.059 Uiso 1 1 calc R U . . .
C19 C 0.09298(15) 0.78407(15) 0.79412(12) 0.0530(4) Uani 1 1 d . . . . .
H19 H -0.010046 0.798958 0.815457 0.064 Uiso 1 1 calc R U . . .
C6 C 0.63799(17) 0.57504(15) 0.40928(11) 0.0521(4) Uani 1 1 d . . . . .
H6 H 0.654505 0.540805 0.353610 0.062 Uiso 1 1 calc R U . . .
C36 C 1.26393(16) 0.11241(13) 0.79927(14) 0.0543(4) Uani 1 1 d . . . . .
H36 H 1.351871 0.092246 0.751390 0.065 Uiso 1 1 calc R U . . .
C30 C 0.72571(18) 0.68927(15) 1.05058(13) 0.0554(4) Uani 1 1 d . . . . .
H30 H 0.796076 0.703043 1.076449 0.066 Uiso 1 1 calc R U . . .
C26 C 0.67772(17) 0.95504(13) 0.73617(14) 0.0542(4) Uani 1 1 d . . . . .
H26 H 0.657163 0.990276 0.791771 0.065 Uiso 1 1 calc R U . . .
C18 C 0.15295(15) 0.87954(14) 0.74040(12) 0.0534(4) Uani 1 1 d . . . . .
H18 H 0.090284 0.959242 0.726270 0.064 Uiso 1 1 calc R U . . .
C38 C 1.12255(18) 0.07294(13) 0.97652(14) 0.0568(4) Uani 1 1 d . . . . .
H38 H 1.114817 0.026599 1.048748 0.068 Uiso 1 1 calc R U . . .
C7 C 0.54226(17) 0.69148(16) 0.40399(11) 0.0549(4) Uani 1 1 d . . . . .
H7 H 0.494706 0.733596 0.343575 0.066 Uiso 1 1 calc R U . . .
C24 C 0.80720(17) 0.93432(15) 0.56281(15) 0.0620(4) Uani 1 1 d . . . . .
H24 H 0.874393 0.955736 0.500471 0.074 Uiso 1 1 calc R U . . .
C31 C 0.57630(18) 0.72585(14) 1.09276(12) 0.0543(4) Uani 1 1 d . . . . .
H31 H 0.545478 0.765562 1.146240 0.065 Uiso 1 1 calc R U . . .
C25 C 0.77773(17) 0.98742(14) 0.64401(15) 0.0600(4) Uani 1 1 d . . . . .
H25 H 0.824526 1.044445 0.637033 0.072 Uiso 1 1 calc R U . . .
C37 C 1.25294(18) 0.04349(13) 0.90574(15) 0.0610(4) Uani 1 1 d . . . . .
H37 H 1.333198 -0.022782 0.929926 0.073 Uiso 1 1 calc R U . . .
C15 C 0.8473(2) 0.32557(17) 0.44079(14) 0.0643(5) Uani 1 1 d . . . . .
H15A H 0.911235 0.244731 0.467514 0.096 Uiso 1 1 calc R U . . .
H15B H 0.899046 0.368036 0.375167 0.096 Uiso 1 1 calc R U . . .
H15C H 0.758045 0.321029 0.426376 0.096 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2210(16) . ?
N1 C1 1.4055(17) . ?
N1 C5 1.4001(18) . ?
N1 C15 1.4671(16) . ?
C28 C12 1.4909(15) . ?
C28 C33 1.3901(17) . ?
C28 C29 1.3935(17) . ?
C16 C21 1.3914(18) . ?
C16 C10 1.5364(17) . ?
C16 C17 1.3878(17) . ?
C12 C11 1.3900(16) . ?
C12 C13 1.4163(16) . ?
C11 C3 1.4021(16) . ?
C11 C10 1.5644(16) . ?
C3 C2 1.3869(16) . ?
C3 C4 1.4133(17) . ?
C14 C2 1.4154(17) . ?
C14 C13 1.3957(16) . ?
C14 C34 1.4884(16) . ?
C33 H33 0.9300 . ?
C33 C32 1.3874(17) . ?
C22 C10 1.5395(18) . ?
C22 C27 1.3917(19) . ?
C22 C23 1.3914(19) . ?
C2 C1 1.4953(16) . ?
C4 C9 1.3781(18) . ?
C4 C5 1.3831(17) . ?
C13 H13 0.9300 . ?
C34 C35 1.3974(18) . ?
C34 C39 1.3847(19) . ?
C21 H21 0.9300 . ?
C21 C20 1.3853(19) . ?
C10 C9 1.5529(17) . ?
C9 C8 1.3820(18) . ?
C27 H27 0.9300 . ?
C27 C26 1.388(2) . ?
C5 C6 1.4012(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.3887(19) . ?
C29 H29 0.9300 . ?
C29 C30 1.3851(19) . ?
C35 H35 0.9300 . ?
C35 C36 1.3811(19) . ?
C39 H39 0.9300 . ?
C39 C38 1.3888(19) . ?
C20 H20 0.9300 . ?
C20 C19 1.378(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(2) . ?
C32 H32 0.9300 . ?
C32 C31 1.374(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.401(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.378(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(2) . ?
C36 H36 0.9300 . ?
C36 C37 1.373(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.375(2) . ?
C26 H26 0.9300 . ?
C26 C25 1.381(2) . ?
C18 H18 0.9300 . ?
C38 H38 0.9300 . ?
C38 C37 1.376(2) . ?
C7 H7 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.373(3) . ?
C31 H31 0.9300 . ?
C25 H25 0.9300 . ?
C37 H37 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C15 117.17(12) . . ?
C5 N1 C1 124.46(10) . . ?
C5 N1 C15 118.34(12) . . ?
C33 C28 C12 121.98(10) . . ?
C33 C28 C29 118.35(11) . . ?
C29 C28 C12 119.61(11) . . ?
C21 C16 C10 120.28(11) . . ?
C17 C16 C21 118.30(11) . . ?
C17 C16 C10 120.90(11) . . ?
C11 C12 C28 125.96(10) . . ?
C11 C12 C13 116.76(10) . . ?
C13 C12 C28 117.27(10) . . ?
C12 C11 C3 116.58(10) . . ?
C12 C11 C10 135.01(10) . . ?
C3 C11 C10 108.28(10) . . ?
C11 C3 C4 110.25(11) . . ?
C2 C3 C11 127.54(11) . . ?
C2 C3 C4 122.21(11) . . ?
C2 C14 C34 125.90(10) . . ?
C13 C14 C2 116.99(10) . . ?
C13 C14 C34 117.04(10) . . ?
C28 C33 H33 119.7 . . ?
C32 C33 C28 120.53(11) . . ?
C32 C33 H33 119.7 . . ?
C27 C22 C10 120.73(11) . . ?
C23 C22 C10 121.54(12) . . ?
C23 C22 C27 117.59(13) . . ?
C3 C2 C14 115.90(10) . . ?
C3 C2 C1 116.42(11) . . ?
C14 C2 C1 127.60(11) . . ?
C9 C4 C3 111.47(11) . . ?
C9 C4 C5 126.08(12) . . ?
C5 C4 C3 122.44(12) . . ?
C12 C13 H13 117.0 . . ?
C14 C13 C12 126.00(11) . . ?
C14 C13 H13 117.0 . . ?
C35 C34 C14 120.74(12) . . ?
C39 C34 C14 120.48(11) . . ?
C39 C34 C35 118.46(12) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.61(12) . . ?
C20 C21 H21 119.7 . . ?
C16 C10 C11 114.74(10) . . ?
C16 C10 C22 114.71(10) . . ?
C16 C10 C9 104.68(9) . . ?
C22 C10 C11 108.05(9) . . ?
C22 C10 C9 112.96(10) . . ?
C9 C10 C11 100.92(9) . . ?
C4 C9 C10 109.00(10) . . ?
C4 C9 C8 118.06(12) . . ?
C8 C9 C10 132.79(12) . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.17(14) . . ?
C26 C27 H27 119.4 . . ?
O1 C1 N1 119.42(11) . . ?
O1 C1 C2 123.12(12) . . ?
N1 C1 C2 117.45(11) . . ?
N1 C5 C6 127.60(12) . . ?
C4 C5 N1 116.48(11) . . ?
C4 C5 C6 115.89(13) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.86(13) . . ?
C18 C17 H17 119.6 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.69(12) . . ?
C30 C29 H29 119.7 . . ?
C34 C35 H35 119.8 . . ?
C36 C35 C34 120.31(14) . . ?
C36 C35 H35 119.8 . . ?
C34 C39 H39 119.7 . . ?
C34 C39 C38 120.67(13) . . ?
C38 C39 H39 119.7 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.55(13) . . ?
C19 C20 H20 119.7 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.97(15) . . ?
C24 C23 H23 119.5 . . ?
C33 C32 H32 119.9 . . ?
C31 C32 C33 120.29(12) . . ?
C31 C32 H32 119.9 . . ?
C9 C8 H8 121.4 . . ?
C9 C8 C7 117.11(13) . . ?
C7 C8 H8 121.4 . . ?
C20 C19 H19 120.3 . . ?
C20 C19 C18 119.46(13) . . ?
C18 C19 H19 120.3 . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.62(13) . . ?
C7 C6 H6 120.7 . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.69(14) . . ?
C37 C36 H36 119.7 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.14(13) . . ?
C31 C30 H30 119.9 . . ?
C27 C26 H26 119.8 . . ?
C25 C26 C27 120.34(15) . . ?
C25 C26 H26 119.8 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.22(13) . . ?
C19 C18 H18 119.9 . . ?
C39 C38 H38 119.9 . . ?
C37 C38 C39 120.19(15) . . ?
C37 C38 H38 119.9 . . ?
C8 C7 H7 117.9 . . ?
C6 C7 C8 124.21(13) . . ?
C6 C7 H7 117.9 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.81(15) . . ?
C25 C24 H24 119.6 . . ?
C32 C31 C30 119.97(12) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C26 C25 H25 120.4 . . ?
C24 C25 C26 119.12(14) . . ?
C24 C25 H25 120.4 . . ?
C36 C37 C38 119.67(13) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C6 C7 178.54(14) . . . . ?
C28 C12 C11 C3 -177.83(11) . . . . ?
C28 C12 C11 C10 6.9(2) . . . . ?
C28 C12 C13 C14 177.59(11) . . . . ?
C28 C33 C32 C31 -0.5(2) . . . . ?
C28 C29 C30 C31 0.1(2) . . . . ?
C16 C21 C20 C19 0.2(2) . . . . ?
C16 C10 C9 C4 -119.74(11) . . . . ?
C16 C10 C9 C8 55.52(18) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C12 C28 C33 C32 178.90(11) . . . . ?
C12 C28 C29 C30 -178.78(13) . . . . ?
C12 C11 C3 C2 0.66(19) . . . . ?
C12 C11 C3 C4 -179.61(11) . . . . ?
C12 C11 C10 C16 -70.48(17) . . . . ?
C12 C11 C10 C22 58.89(17) . . . . ?
C12 C11 C10 C9 177.62(13) . . . . ?
C11 C12 C13 C14 -3.30(18) . . . . ?
C11 C3 C2 C14 -4.48(19) . . . . ?
C11 C3 C2 C1 172.45(12) . . . . ?
C11 C3 C4 C9 3.01(16) . . . . ?
C11 C3 C4 C5 -176.09(12) . . . . ?
C11 C10 C9 C4 -0.32(13) . . . . ?
C11 C10 C9 C8 174.94(14) . . . . ?
C3 C11 C10 C16 113.96(11) . . . . ?
C3 C11 C10 C22 -116.67(11) . . . . ?
C3 C11 C10 C9 2.06(12) . . . . ?
C3 C2 C1 O1 -170.72(13) . . . . ?
C3 C2 C1 N1 8.40(17) . . . . ?
C3 C4 C9 C10 -1.54(15) . . . . ?
C3 C4 C9 C8 -177.60(12) . . . . ?
C3 C4 C5 N1 -0.92(19) . . . . ?
C3 C4 C5 C6 177.04(12) . . . . ?
C14 C2 C1 O1 5.8(2) . . . . ?
C14 C2 C1 N1 -175.08(12) . . . . ?
C14 C34 C35 C36 173.46(11) . . . . ?
C14 C34 C39 C38 -172.96(12) . . . . ?
C33 C28 C12 C11 57.94(17) . . . . ?
C33 C28 C12 C13 -123.04(12) . . . . ?
C33 C28 C29 C30 -1.49(19) . . . . ?
C33 C32 C31 C30 -0.9(2) . . . . ?
C22 C10 C9 C4 114.79(12) . . . . ?
C22 C10 C9 C8 -69.94(18) . . . . ?
C22 C27 C26 C25 0.8(2) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C2 C3 C4 C9 -177.24(11) . . . . ?
C2 C3 C4 C5 3.7(2) . . . . ?
C2 C14 C13 C12 -0.56(18) . . . . ?
C2 C14 C34 C35 46.55(17) . . . . ?
C2 C14 C34 C39 -140.03(13) . . . . ?
C4 C3 C2 C14 175.81(11) . . . . ?
C4 C3 C2 C1 -7.25(18) . . . . ?
C4 C9 C8 C7 0.1(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C13 C12 C11 C3 3.14(16) . . . . ?
C13 C12 C11 C10 -172.14(12) . . . . ?
C13 C14 C2 C3 4.16(16) . . . . ?
C13 C14 C2 C1 -172.38(12) . . . . ?
C13 C14 C34 C35 -130.30(12) . . . . ?
C13 C14 C34 C39 43.12(16) . . . . ?
C34 C14 C2 C3 -172.70(11) . . . . ?
C34 C14 C2 C1 10.8(2) . . . . ?
C34 C14 C13 C12 176.58(11) . . . . ?
C34 C35 C36 C37 -0.4(2) . . . . ?
C34 C39 C38 C37 -0.7(2) . . . . ?
C21 C16 C10 C11 -30.56(15) . . . . ?
C21 C16 C10 C22 -156.54(11) . . . . ?
C21 C16 C10 C9 79.10(13) . . . . ?
C21 C16 C17 C18 0.93(19) . . . . ?
C21 C20 C19 C18 -0.4(2) . . . . ?
C10 C16 C21 C20 -172.25(11) . . . . ?
C10 C16 C17 C18 172.66(12) . . . . ?
C10 C11 C3 C2 177.15(12) . . . . ?
C10 C11 C3 C4 -3.12(14) . . . . ?
C10 C22 C27 C26 174.63(11) . . . . ?
C10 C22 C23 C24 -174.83(12) . . . . ?
C10 C9 C8 C7 -174.83(14) . . . . ?
C9 C4 C5 N1 -179.89(12) . . . . ?
C9 C4 C5 C6 -1.9(2) . . . . ?
C9 C8 C7 C6 -1.1(2) . . . . ?
C27 C22 C10 C16 45.75(15) . . . . ?
C27 C22 C10 C11 -83.64(13) . . . . ?
C27 C22 C10 C9 165.60(11) . . . . ?
C27 C22 C23 C24 0.84(19) . . . . ?
C27 C26 C25 C24 -0.2(2) . . . . ?
C1 N1 C5 C4 2.6(2) . . . . ?
C1 N1 C5 C6 -175.08(13) . . . . ?
C5 N1 C1 O1 172.74(13) . . . . ?
C5 N1 C1 C2 -6.40(19) . . . . ?
C5 C4 C9 C10 177.52(12) . . . . ?
C5 C4 C9 C8 1.5(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C17 C16 C21 C20 -0.47(18) . . . . ?
C17 C16 C10 C11 157.88(11) . . . . ?
C17 C16 C10 C22 31.89(15) . . . . ?
C17 C16 C10 C9 -92.47(13) . . . . ?
C29 C28 C12 C11 -124.88(13) . . . . ?
C29 C28 C12 C13 54.14(15) . . . . ?
C29 C28 C33 C32 1.68(18) . . . . ?
C29 C30 C31 C32 1.1(2) . . . . ?
C35 C34 C39 C38 0.60(19) . . . . ?
C35 C36 C37 C38 0.3(2) . . . . ?
C39 C34 C35 C36 -0.09(18) . . . . ?
C39 C38 C37 C36 0.2(2) . . . . ?
C20 C19 C18 C17 0.9(2) . . . . ?
C23 C22 C10 C16 -138.72(12) . . . . ?
C23 C22 C10 C11 91.90(13) . . . . ?
C23 C22 C10 C9 -18.86(16) . . . . ?
C23 C22 C27 C26 -1.08(18) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
C15 N1 C1 O1 -5.2(2) . . . . ?
C15 N1 C1 C2 175.69(12) . . . . ?
C15 N1 C5 C4 -179.51(13) . . . . ?
C15 N1 C5 C6 2.8(2) . . . . ?

_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_20211227a
_database_code_depnum_ccdc_archive 'CCDC 2189110'
loop_
_audit_author_name
_audit_author_address
'Shaoyin Wang'
;Wannan Medical College
China
;
_audit_update_record             
;
2022-07-09 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C55 H45 N O3'
_chemical_formula_sum            'C55 H45 N O3'
_chemical_formula_weight         767.92
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.978(6)
_cell_length_b                   13.234(6)
_cell_length_c                   13.515(6)
_cell_angle_alpha                72.580(15)
_cell_angle_beta                 78.270(15)
_cell_angle_gamma                74.539(15)
_cell_volume                     2115.3(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9273
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.410
_cell_measurement_theta_min      2.575
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0770 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.8794. The λ/2 correction factor is Not present.'
_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    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            71040
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.575
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5401
_reflns_number_total             9697
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0138(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         9697
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.006
_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)+(0.0607P)²+0.3211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28),
  C30(H30), C31(H31), C34(H34), C37(H37), C38(H38), C39(H39), C40(H40),
 C41(H41), C43(H43), C44(H44), C46(H46), C47(H47), C50(H50), C51(H51), C53(H53),
  C54(H54)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C32(H32A,H32B,H32C), C48(H48A,H48B,H48C), C55(H55A,H55B,
 H55C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65542(10) 0.41746(10) 0.64469(11) 0.0554(4) Uani 1 1 d . . . . .
O2 O 0.75714(11) 0.41544(10) 0.80952(11) 0.0577(4) Uani 1 1 d . . . . .
H2 H 0.719272 0.427799 0.763674 0.087 Uiso 1 1 calc R U . . .
O3 O 0.51641(9) 0.12035(9) 0.64699(10) 0.0447(3) Uani 1 1 d . . . . .
N1 N 0.77036(11) 0.25862(11) 0.62781(11) 0.0403(3) Uani 1 1 d . . . . .
C1 C 0.66683(14) 0.32321(14) 0.63932(14) 0.0421(4) Uani 1 1 d . . . . .
C2 C 0.57645(13) 0.27567(13) 0.64490(13) 0.0387(4) Uani 1 1 d . . . . .
C3 C 0.59690(13) 0.17104(14) 0.63895(13) 0.0381(4) Uani 1 1 d . . . . .
C4 C 0.70348(13) 0.10371(14) 0.63171(13) 0.0376(4) Uani 1 1 d . . . . .
C5 C 0.72326(15) -0.00621(14) 0.63394(14) 0.0450(4) Uani 1 1 d . . . . .
H5 H 0.665654 -0.037884 0.639649 0.054 Uiso 1 1 calc R U . . .
C6 C 0.82700(15) -0.06795(16) 0.62779(16) 0.0521(5) Uani 1 1 d . . . . .
H6 H 0.839404 -0.141176 0.630397 0.062 Uiso 1 1 calc R U . . .
C7 C 0.91309(15) -0.01999(16) 0.61765(15) 0.0513(5) Uani 1 1 d . . . . .
H7 H 0.983241 -0.061347 0.612340 0.062 Uiso 1 1 calc R U . . .
C8 C 0.89597(14) 0.08734(16) 0.61538(14) 0.0474(5) Uani 1 1 d . . . . .
H8 H 0.954410 0.118383 0.608019 0.057 Uiso 1 1 calc R U . . .
C9 C 0.79082(13) 0.15050(14) 0.62409(13) 0.0384(4) Uani 1 1 d . . . . .
C10 C 0.86117(13) 0.30833(14) 0.61567(14) 0.0428(4) Uani 1 1 d . . . . .
C11 C 0.88987(14) 0.32917(14) 0.69524(15) 0.0452(4) Uani 1 1 d . . . . .
H11 H 0.952643 0.355415 0.678893 0.054 Uiso 1 1 calc R U . . .
C12 C 0.83789(15) 0.31754(14) 0.80829(15) 0.0458(4) Uani 1 1 d . . . . .
C13 C 0.91252(15) 0.34360(15) 0.50623(15) 0.0487(5) Uani 1 1 d . . . . .
C14 C 1.01992(17) 0.34891(19) 0.48251(18) 0.0675(6) Uani 1 1 d . . . . .
H14 H 1.063640 0.323671 0.535381 0.081 Uiso 1 1 calc R U . . .
C15 C 1.0630(2) 0.3916(2) 0.3806(2) 0.0821(8) Uani 1 1 d . . . . .
H15 H 1.135646 0.393808 0.365439 0.099 Uiso 1 1 calc R U . . .
C16 C 0.9999(3) 0.4302(2) 0.3024(2) 0.0867(8) Uani 1 1 d . . . . .
H16 H 1.028717 0.460875 0.234469 0.104 Uiso 1 1 calc R U . . .
C17 C 0.8947(3) 0.4238(3) 0.3241(2) 0.1093(11) Uani 1 1 d . . . . .
H17 H 0.851748 0.448704 0.270619 0.131 Uiso 1 1 calc R U . . .
C18 C 0.8514(2) 0.3803(2) 0.42514(18) 0.0876(9) Uani 1 1 d . . . . .
H18 H 0.779327 0.375757 0.438794 0.105 Uiso 1 1 calc R U . . .
C19 C 0.91984(15) 0.31487(14) 0.87673(15) 0.0470(5) Uani 1 1 d . . . . .
C20 C 0.88607(18) 0.36030(17) 0.96065(16) 0.0593(5) Uani 1 1 d . . . . .
H20 H 0.813218 0.390089 0.976532 0.071 Uiso 1 1 calc R U . . .
C21 C 0.9588(2) 0.36216(19) 1.02124(18) 0.0678(6) Uani 1 1 d . . . . .
H21 H 0.933727 0.393442 1.077208 0.081 Uiso 1 1 calc R U . . .
C22 C 1.06795(19) 0.31876(18) 1.00110(18) 0.0639(6) Uani 1 1 d . . . . .
C23 C 1.10101(19) 0.27135(19) 0.91892(18) 0.0706(6) Uani 1 1 d . . . . .
H23 H 1.173634 0.239974 0.904226 0.085 Uiso 1 1 calc R U . . .
C24 C 1.02864(17) 0.26931(18) 0.85767(17) 0.0619(6) Uani 1 1 d . . . . .
H24 H 1.053554 0.236696 0.802595 0.074 Uiso 1 1 calc R U . . .
C25 C 1.1481(2) 0.3243(2) 1.0664(2) 0.0983(9) Uani 1 1 d . . . . .
H25A H 1.131973 0.395570 1.077450 0.148 Uiso 1 1 calc R U . . .
H25B H 1.219927 0.309413 1.030142 0.148 Uiso 1 1 calc R U . . .
H25C H 1.142977 0.271508 1.132679 0.148 Uiso 1 1 calc R U . . .
C26 C 0.78817(15) 0.21779(14) 0.85255(14) 0.0446(4) Uani 1 1 d . . . . .
C27 C 0.85163(16) 0.11387(15) 0.85823(15) 0.0511(5) Uani 1 1 d . . . . .
H27 H 0.926211 0.104248 0.842642 0.061 Uiso 1 1 calc R U . . .
C28 C 0.80559(17) 0.02476(16) 0.88667(15) 0.0539(5) Uani 1 1 d . . . . .
H28 H 0.849639 -0.043940 0.889766 0.065 Uiso 1 1 calc R U . . .
C29 C 0.69489(17) 0.03603(16) 0.91066(15) 0.0543(5) Uani 1 1 d . . . . .
C30 C 0.63281(17) 0.13839(17) 0.91093(16) 0.0603(6) Uani 1 1 d . . . . .
H30 H 0.558607 0.147160 0.930074 0.072 Uiso 1 1 calc R U . . .
C31 C 0.67791(16) 0.22859(16) 0.88346(16) 0.0550(5) Uani 1 1 d . . . . .
H31 H 0.634226 0.296348 0.885744 0.066 Uiso 1 1 calc R U . . .
C32 C 0.6439(2) -0.05954(19) 0.9326(2) 0.0815(7) Uani 1 1 d . . . . .
H32A H 0.682560 -0.105494 0.887851 0.122 Uiso 1 1 calc R U . . .
H32B H 0.570133 -0.034127 0.919523 0.122 Uiso 1 1 calc R U . . .
H32C H 0.646379 -0.099932 1.004405 0.122 Uiso 1 1 calc R U . . .
C33 C 0.46293(13) 0.33149(14) 0.66674(14) 0.0420(4) Uani 1 1 d . . . . .
C34 C 0.38664(14) 0.28867(15) 0.65288(16) 0.0489(5) Uani 1 1 d . . . . .
H34 H 0.314622 0.321138 0.668996 0.059 Uiso 1 1 calc R U . . .
C35 C 0.41338(13) 0.18912(14) 0.61186(15) 0.0439(4) Uani 1 1 d . . . . .
C36 C 0.42909(13) 0.42695(15) 0.71315(15) 0.0442(4) Uani 1 1 d . . . . .
C37 C 0.40377(19) 0.41117(19) 0.81978(18) 0.0683(6) Uani 1 1 d . . . . .
H37 H 0.412843 0.340866 0.863014 0.082 Uiso 1 1 calc R U . . .
C38 C 0.3649(2) 0.4985(2) 0.8637(2) 0.0860(8) Uani 1 1 d . . . . .
H38 H 0.349103 0.486556 0.936035 0.103 Uiso 1 1 calc R U . . .
C39 C 0.34989(19) 0.6020(2) 0.8011(2) 0.0768(7) Uani 1 1 d . . . . .
H39 H 0.322776 0.660593 0.830425 0.092 Uiso 1 1 calc R U . . .
C40 C 0.37491(18) 0.61904(18) 0.6949(2) 0.0690(6) Uani 1 1 d . . . . .
H40 H 0.364823 0.689525 0.652038 0.083 Uiso 1 1 calc R U . . .
C41 C 0.41508(16) 0.53215(16) 0.65096(17) 0.0550(5) Uani 1 1 d . . . . .
H41 H 0.432847 0.544701 0.578753 0.066 Uiso 1 1 calc R U . . .
C42 C 0.33275(13) 0.11719(14) 0.66424(15) 0.0429(4) Uani 1 1 d . . . . .
C43 C 0.32252(17) 0.07437(19) 0.77174(17) 0.0607(6) Uani 1 1 d . . . . .
H43 H 0.362424 0.092670 0.811056 0.073 Uiso 1 1 calc R U . . .
C44 C 0.25412(18) 0.00500(19) 0.82153(17) 0.0653(6) Uani 1 1 d . . . . .
H44 H 0.249236 -0.022924 0.893755 0.078 Uiso 1 1 calc R U . . .
C45 C 0.19279(15) -0.02383(16) 0.76646(17) 0.0550(5) Uani 1 1 d . . . . .
C46 C 0.20168(17) 0.02071(18) 0.65964(17) 0.0625(6) Uani 1 1 d . . . . .
H46 H 0.160721 0.003506 0.620520 0.075 Uiso 1 1 calc R U . . .
C47 C 0.27020(15) 0.09050(17) 0.60918(16) 0.0544(5) Uani 1 1 d . . . . .
H47 H 0.273924 0.119664 0.537152 0.065 Uiso 1 1 calc R U . . .
C48 C 0.12161(19) -0.1031(2) 0.8210(2) 0.0824(8) Uani 1 1 d . . . . .
H48A H 0.154811 -0.172195 0.806582 0.124 Uiso 1 1 calc R U . . .
H48B H 0.052680 -0.076375 0.796063 0.124 Uiso 1 1 calc R U . . .
H48C H 0.112035 -0.111295 0.895099 0.124 Uiso 1 1 calc R U . . .
C49 C 0.42695(14) 0.21548(14) 0.49255(15) 0.0436(4) Uani 1 1 d . . . . .
C50 C 0.49587(15) 0.14354(15) 0.43952(16) 0.0501(5) Uani 1 1 d . . . . .
H50 H 0.538872 0.081146 0.476627 0.060 Uiso 1 1 calc R U . . .
C51 C 0.50200(17) 0.16267(16) 0.33233(17) 0.0572(5) Uani 1 1 d . . . . .
H51 H 0.549419 0.113250 0.298539 0.069 Uiso 1 1 calc R U . . .
C52 C 0.43862(18) 0.25430(17) 0.27451(17) 0.0577(5) Uani 1 1 d . . . . .
C53 C 0.37047(18) 0.32657(17) 0.32730(18) 0.0635(6) Uani 1 1 d . . . . .
H53 H 0.327251 0.388664 0.290020 0.076 Uiso 1 1 calc R U . . .
C54 C 0.36488(16) 0.30885(16) 0.43459(18) 0.0576(5) Uani 1 1 d . . . . .
H54 H 0.319410 0.359644 0.467925 0.069 Uiso 1 1 calc R U . . .
C55 C 0.4455(2) 0.2769(2) 0.15717(19) 0.0859(8) Uani 1 1 d . . . . .
H55A H 0.499693 0.220885 0.133202 0.129 Uiso 1 1 calc R U . . .
H55B H 0.464243 0.345852 0.124142 0.129 Uiso 1 1 calc R U . . .
H55C H 0.377013 0.278239 0.139634 0.129 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.239(2) . ?
O2 H2 0.8200 . ?
O2 C12 1.435(2) . ?
O3 C3 1.355(2) . ?
O3 C35 1.481(2) . ?
N1 C1 1.394(2) . ?
N1 C9 1.398(2) . ?
N1 C10 1.456(2) . ?
C1 C2 1.451(2) . ?
C2 C3 1.362(2) . ?
C2 C33 1.476(2) . ?
C3 C4 1.434(2) . ?
C4 C5 1.400(2) . ?
C4 C9 1.403(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(2) . ?
C10 C11 1.329(3) . ?
C10 C13 1.484(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.519(3) . ?
C12 C19 1.532(3) . ?
C12 C26 1.530(3) . ?
C13 C14 1.381(3) . ?
C13 C18 1.377(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.362(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.356(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 C24 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 C23 1.375(3) . ?
C22 C25 1.523(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.391(3) . ?
C26 C31 1.388(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.381(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.384(3) . ?
C29 C30 1.380(3) . ?
C29 C32 1.506(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.387(3) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.332(2) . ?
C33 C36 1.500(2) . ?
C34 H34 0.9300 . ?
C34 C35 1.510(3) . ?
C35 C42 1.526(2) . ?
C35 C49 1.528(3) . ?
C36 C37 1.376(3) . ?
C36 C41 1.380(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.387(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.364(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.368(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.382(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.385(3) . ?
C42 C47 1.376(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.380(3) . ?
C44 H44 0.9300 . ?
C44 C45 1.380(3) . ?
C45 C46 1.380(3) . ?
C45 C48 1.508(3) . ?
C46 H46 0.9300 . ?
C46 C47 1.387(3) . ?
C47 H47 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.384(3) . ?
C49 C54 1.391(3) . ?
C50 H50 0.9300 . ?
C50 C51 1.383(3) . ?
C51 H51 0.9300 . ?
C51 C52 1.386(3) . ?
C52 C53 1.381(3) . ?
C52 C55 1.512(3) . ?
C53 H53 0.9300 . ?
C53 C54 1.388(3) . ?
C54 H54 0.9300 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 H2 109.5 . . ?
C3 O3 C35 117.18(13) . . ?
C1 N1 C9 123.37(14) . . ?
C1 N1 C10 117.71(14) . . ?
C9 N1 C10 118.89(14) . . ?
O1 C1 N1 119.42(15) . . ?
O1 C1 C2 122.87(16) . . ?
N1 C1 C2 117.70(15) . . ?
C1 C2 C33 123.12(15) . . ?
C3 C2 C1 118.70(15) . . ?
C3 C2 C33 117.93(15) . . ?
O3 C3 C2 121.88(15) . . ?
O3 C3 C4 114.79(15) . . ?
C2 C3 C4 123.17(15) . . ?
C5 C4 C3 122.83(16) . . ?
C5 C4 C9 119.19(16) . . ?
C9 C4 C3 117.96(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.77(17) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.50(18) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.90(17) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.25(17) . . ?
C9 C8 H8 119.9 . . ?
N1 C9 C4 118.99(15) . . ?
N1 C9 C8 121.65(15) . . ?
C8 C9 C4 119.34(16) . . ?
N1 C10 C13 114.85(16) . . ?
C11 C10 N1 122.50(16) . . ?
C11 C10 C13 122.40(16) . . ?
C10 C11 H11 114.4 . . ?
C10 C11 C12 131.17(17) . . ?
C12 C11 H11 114.4 . . ?
O2 C12 C11 106.16(14) . . ?
O2 C12 C19 105.91(15) . . ?
O2 C12 C26 110.87(15) . . ?
C11 C12 C19 110.32(15) . . ?
C11 C12 C26 112.84(15) . . ?
C26 C12 C19 110.43(15) . . ?
C14 C13 C10 121.91(19) . . ?
C18 C13 C10 120.22(18) . . ?
C18 C13 C14 117.7(2) . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 121.4(2) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C12 119.87(18) . . ?
C20 C19 C24 117.40(19) . . ?
C24 C19 C12 122.72(17) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.1 . . ?
C20 C21 C22 121.8(2) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 C25 121.4(2) . . ?
C23 C22 C21 117.1(2) . . ?
C23 C22 C25 121.5(2) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.3(2) . . ?
C23 C24 H24 119.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C12 120.81(16) . . ?
C31 C26 C12 121.05(17) . . ?
C31 C26 C27 118.06(17) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 121.00(18) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C29 121.05(19) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 C32 121.1(2) . . ?
C30 C29 C28 117.68(18) . . ?
C30 C29 C32 121.2(2) . . ?
C29 C30 H30 119.1 . . ?
C29 C30 C31 121.88(19) . . ?
C31 C30 H30 119.1 . . ?
C26 C31 H31 120.0 . . ?
C30 C31 C26 120.05(19) . . ?
C30 C31 H31 120.0 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C2 C33 C36 123.43(15) . . ?
C34 C33 C2 117.83(16) . . ?
C34 C33 C36 118.47(15) . . ?
C33 C34 H34 119.0 . . ?
C33 C34 C35 122.10(16) . . ?
C35 C34 H34 119.0 . . ?
O3 C35 C34 108.05(14) . . ?
O3 C35 C42 103.28(14) . . ?
O3 C35 C49 107.98(14) . . ?
C34 C35 C42 110.98(15) . . ?
C34 C35 C49 113.25(15) . . ?
C42 C35 C49 112.66(15) . . ?
C37 C36 C33 120.06(18) . . ?
C37 C36 C41 118.24(18) . . ?
C41 C36 C33 121.54(18) . . ?
C36 C37 H37 119.5 . . ?
C36 C37 C38 121.0(2) . . ?
C38 C37 H37 119.5 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 120.1(2) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 120.2 . . ?
C38 C39 C40 119.7(2) . . ?
C40 C39 H39 120.2 . . ?
C39 C40 H40 119.8 . . ?
C39 C40 C41 120.4(2) . . ?
C41 C40 H40 119.8 . . ?
C36 C41 C40 120.7(2) . . ?
C36 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C43 C42 C35 119.36(17) . . ?
C47 C42 C35 122.95(17) . . ?
C47 C42 C43 117.67(17) . . ?
C42 C43 H43 119.4 . . ?
C44 C43 C42 121.13(19) . . ?
C44 C43 H43 119.4 . . ?
C43 C44 H44 119.3 . . ?
C43 C44 C45 121.5(2) . . ?
C45 C44 H44 119.3 . . ?
C44 C45 C48 121.0(2) . . ?
C46 C45 C44 117.19(19) . . ?
C46 C45 C48 121.7(2) . . ?
C45 C46 H46 119.2 . . ?
C45 C46 C47 121.62(19) . . ?
C47 C46 H46 119.2 . . ?
C42 C47 C46 120.90(19) . . ?
C42 C47 H47 119.5 . . ?
C46 C47 H47 119.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 C35 120.91(17) . . ?
C50 C49 C54 117.99(19) . . ?
C54 C49 C35 120.96(17) . . ?
C49 C50 H50 119.4 . . ?
C51 C50 C49 121.23(19) . . ?
C51 C50 H50 119.4 . . ?
C50 C51 H51 119.5 . . ?
C50 C51 C52 121.0(2) . . ?
C52 C51 H51 119.5 . . ?
C51 C52 C55 121.6(2) . . ?
C53 C52 C51 117.7(2) . . ?
C53 C52 C55 120.7(2) . . ?
C52 C53 H53 119.2 . . ?
C52 C53 C54 121.6(2) . . ?
C54 C53 H53 119.2 . . ?
C49 C54 H54 119.8 . . ?
C53 C54 C49 120.3(2) . . ?
C53 C54 H54 119.8 . . ?
C52 C55 H55A 109.5 . . ?
C52 C55 H55B 109.5 . . ?
C52 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.82 2.01 2.801(2) 163.2 . yes

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 -179.58(17) . . . . ?
O1 C1 C2 C33 -5.6(3) . . . . ?
O2 C12 C19 C20 31.5(2) . . . . ?
O2 C12 C19 C24 -147.71(18) . . . . ?
O2 C12 C26 C27 179.56(16) . . . . ?
O2 C12 C26 C31 2.7(2) . . . . ?
O3 C3 C4 C5 -0.7(2) . . . . ?
O3 C3 C4 C9 -179.46(15) . . . . ?
O3 C35 C42 C43 55.1(2) . . . . ?
O3 C35 C42 C47 -123.56(18) . . . . ?
O3 C35 C49 C50 30.4(2) . . . . ?
O3 C35 C49 C54 -154.16(16) . . . . ?
N1 C1 C2 C3 0.2(2) . . . . ?
N1 C1 C2 C33 174.18(15) . . . . ?
N1 C10 C11 C12 -5.1(3) . . . . ?
N1 C10 C13 C14 -152.35(19) . . . . ?
N1 C10 C13 C18 32.7(3) . . . . ?
C1 N1 C9 C4 0.3(2) . . . . ?
C1 N1 C9 C8 -178.19(16) . . . . ?
C1 N1 C10 C11 75.0(2) . . . . ?
C1 N1 C10 C13 -99.33(19) . . . . ?
C1 C2 C3 O3 177.84(15) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C1 C2 C33 C34 169.02(18) . . . . ?
C1 C2 C33 C36 -17.0(3) . . . . ?
C2 C3 C4 C5 174.81(17) . . . . ?
C2 C3 C4 C9 -3.9(3) . . . . ?
C2 C33 C34 C35 -2.6(3) . . . . ?
C2 C33 C36 C37 -92.4(2) . . . . ?
C2 C33 C36 C41 92.2(2) . . . . ?
C3 O3 C35 C34 -43.8(2) . . . . ?
C3 O3 C35 C42 -161.41(14) . . . . ?
C3 O3 C35 C49 79.07(17) . . . . ?
C3 C2 C33 C34 -16.9(3) . . . . ?
C3 C2 C33 C36 157.01(17) . . . . ?
C3 C4 C5 C6 -179.34(17) . . . . ?
C3 C4 C9 N1 2.4(2) . . . . ?
C3 C4 C9 C8 -179.08(16) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C5 C4 C9 N1 -176.44(15) . . . . ?
C5 C4 C9 C8 2.1(2) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 N1 176.44(17) . . . . ?
C7 C8 C9 C4 -2.1(3) . . . . ?
C9 N1 C1 O1 178.10(16) . . . . ?
C9 N1 C1 C2 -1.7(2) . . . . ?
C9 N1 C10 C11 -107.0(2) . . . . ?
C9 N1 C10 C13 78.7(2) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C10 N1 C1 O1 -4.0(2) . . . . ?
C10 N1 C1 C2 176.26(16) . . . . ?
C10 N1 C9 C4 -177.56(15) . . . . ?
C10 N1 C9 C8 3.9(2) . . . . ?
C10 C11 C12 O2 -84.9(2) . . . . ?
C10 C11 C12 C19 160.78(19) . . . . ?
C10 C11 C12 C26 36.7(3) . . . . ?
C10 C13 C14 C15 -174.0(2) . . . . ?
C10 C13 C18 C17 173.4(3) . . . . ?
C11 C10 C13 C14 33.3(3) . . . . ?
C11 C10 C13 C18 -141.6(2) . . . . ?
C11 C12 C19 C20 146.01(17) . . . . ?
C11 C12 C19 C24 -33.2(2) . . . . ?
C11 C12 C26 C27 60.6(2) . . . . ?
C11 C12 C26 C31 -116.3(2) . . . . ?
C12 C19 C20 C21 -177.80(19) . . . . ?
C12 C19 C24 C23 177.9(2) . . . . ?
C12 C26 C27 C28 -172.46(18) . . . . ?
C12 C26 C31 C30 171.91(18) . . . . ?
C13 C10 C11 C12 168.87(18) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C13 C18 C17 -1.8(4) . . . . ?
C14 C15 C16 C17 -2.1(5) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C18 C13 C14 C15 1.0(4) . . . . ?
C19 C12 C26 C27 -63.4(2) . . . . ?
C19 C12 C26 C31 119.8(2) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C19 C24 C23 -1.4(3) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
C20 C21 C22 C25 178.1(2) . . . . ?
C21 C22 C23 C24 1.4(4) . . . . ?
C22 C23 C24 C19 -0.1(4) . . . . ?
C24 C19 C20 C21 1.5(3) . . . . ?
C25 C22 C23 C24 -178.0(2) . . . . ?
C26 C12 C19 C20 -88.6(2) . . . . ?
C26 C12 C19 C24 92.2(2) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C27 C26 C31 C30 -5.0(3) . . . . ?
C27 C28 C29 C30 -3.6(3) . . . . ?
C27 C28 C29 C32 174.7(2) . . . . ?
C28 C29 C30 C31 3.0(3) . . . . ?
C29 C30 C31 C26 1.3(3) . . . . ?
C31 C26 C27 C28 4.5(3) . . . . ?
C32 C29 C30 C31 -175.2(2) . . . . ?
C33 C2 C3 O3 3.5(3) . . . . ?
C33 C2 C3 C4 -171.68(15) . . . . ?
C33 C34 C35 O3 31.2(2) . . . . ?
C33 C34 C35 C42 143.72(19) . . . . ?
C33 C34 C35 C49 -88.4(2) . . . . ?
C33 C36 C37 C38 -175.3(2) . . . . ?
C33 C36 C41 C40 174.35(18) . . . . ?
C34 C33 C36 C37 81.5(2) . . . . ?
C34 C33 C36 C41 -93.8(2) . . . . ?
C34 C35 C42 C43 -60.4(2) . . . . ?
C34 C35 C42 C47 120.9(2) . . . . ?
C34 C35 C49 C50 149.99(16) . . . . ?
C34 C35 C49 C54 -34.6(2) . . . . ?
C35 O3 C3 C2 28.9(2) . . . . ?
C35 O3 C3 C4 -155.54(15) . . . . ?
C35 C42 C43 C44 -177.03(19) . . . . ?
C35 C42 C47 C46 176.94(18) . . . . ?
C35 C49 C50 C51 174.65(17) . . . . ?
C35 C49 C54 C53 -173.73(17) . . . . ?
C36 C33 C34 C35 -176.83(17) . . . . ?
C36 C37 C38 C39 0.9(4) . . . . ?
C37 C36 C41 C40 -1.1(3) . . . . ?
C37 C38 C39 C40 -1.0(4) . . . . ?
C38 C39 C40 C41 0.1(4) . . . . ?
C39 C40 C41 C36 1.0(3) . . . . ?
C41 C36 C37 C38 0.2(3) . . . . ?
C42 C35 C49 C50 -83.0(2) . . . . ?
C42 C35 C49 C54 92.4(2) . . . . ?
C42 C43 C44 C45 -0.4(3) . . . . ?
C43 C42 C47 C46 -1.8(3) . . . . ?
C43 C44 C45 C46 -0.8(3) . . . . ?
C43 C44 C45 C48 177.6(2) . . . . ?
C44 C45 C46 C47 0.8(3) . . . . ?
C45 C46 C47 C42 0.5(3) . . . . ?
C47 C42 C43 C44 1.7(3) . . . . ?
C48 C45 C46 C47 -177.6(2) . . . . ?
C49 C35 C42 C43 171.37(17) . . . . ?
C49 C35 C42 C47 -7.3(2) . . . . ?
C49 C50 C51 C52 -0.5(3) . . . . ?
C50 C49 C54 C53 1.9(3) . . . . ?
C50 C51 C52 C53 1.0(3) . . . . ?
C50 C51 C52 C55 179.24(19) . . . . ?
C51 C52 C53 C54 -0.1(3) . . . . ?
C52 C53 C54 C49 -1.4(3) . . . . ?
C54 C49 C50 C51 -0.9(3) . . . . ?
C55 C52 C53 C54 -178.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
