# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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 
# 
# 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_fanzhp0513
_database_code_depnum_ccdc_archive 'CCDC 1536577'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2015-05-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C38 H48 N2 O2'
_chemical_formula_sum            'C38 H48 N2 O2'
_chemical_formula_weight         564.78
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   4.7498(6)
_cell_length_b                   8.7857(13)
_cell_length_c                   19.509(5)
_cell_angle_alpha                90.336(15)
_cell_angle_beta                 93.846(14)
_cell_angle_gamma                99.239(11)
_cell_volume                     801.6(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    490
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      20.3080
_cell_measurement_theta_min      4.1830
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.1851
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5090
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.89
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   88.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   90.50   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   17.50   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -30.0000 23

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   65.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega  -68.00  -41.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  125.0000  148.0000 18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0051549000
_diffrn_orient_matrix_UB_12      0.0759256000
_diffrn_orient_matrix_UB_13      0.0118384000
_diffrn_orient_matrix_UB_21      -0.0218575000
_diffrn_orient_matrix_UB_22      0.0234961000
_diffrn_orient_matrix_UB_23      -0.0344071000
_diffrn_orient_matrix_UB_31      -0.1499830000
_diffrn_orient_matrix_UB_32      -0.0193769000
_diffrn_orient_matrix_UB_33      0.0020680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1064
_reflns_number_total             3143
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2191
_refine_ls_R_factor_gt           0.0828
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.2294
_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. 
;
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.4909(6) -0.5878(3) 0.36558(17) 0.0661(10) Uani 1 d . . .
N1 N 0.8329(7) 0.0134(4) 0.2951(2) 0.0543(10) Uani 1 d . . .
C1 C -0.0665(8) -0.3546(5) 0.5202(2) 0.0513(12) Uani 1 d . . .
H1 H -0.1101 -0.2600 0.5338 0.062 Uiso 1 calc . . R
C2 C 0.1216(8) -0.3649(5) 0.4696(2) 0.0477(11) Uani 1 d . . .
C3 C 0.1877(8) -0.5086(5) 0.4503(2) 0.0478(11) Uani 1 d . . .
C4 C 0.3896(9) -0.4866(5) 0.3942(2) 0.0490(12) Uani 1 d . . .
C5 C 0.4456(8) -0.3187(5) 0.3842(2) 0.0438(11) Uani 1 d . . .
C6 C 0.2886(8) -0.2467(5) 0.4284(2) 0.0427(11) Uani 1 d . . .
C7 C 0.3131(8) -0.0871(5) 0.4275(2) 0.0481(11) Uani 1 d . . .
H7 H 0.2089 -0.0369 0.4565 0.058 Uiso 1 calc . . R
C8 C 0.4932(8) -0.0023(5) 0.3832(2) 0.0498(12) Uani 1 d . . .
H8 H 0.5097 0.1047 0.3834 0.060 Uiso 1 calc . . R
C9 C 0.6512(8) -0.0753(5) 0.3380(2) 0.0462(11) Uani 1 d . . .
C10 C 0.6206(8) -0.2370(5) 0.3387(2) 0.0477(11) Uani 1 d . . .
H10 H 0.7178 -0.2888 0.3086 0.057 Uiso 1 calc . . R
C11 C 0.8522(10) 0.1785(5) 0.2948(3) 0.0729(15) Uani 1 d . . .
H11A H 0.6742 0.2049 0.2764 0.109 Uiso 1 calc . . GR
H11B H 1.0029 0.2221 0.2669 0.109 Uiso 1 calc . . GR
H11C H 0.8923 0.2186 0.3409 0.109 Uiso 1 calc . . GR
C12 C 0.9665(8) -0.0569(5) 0.2409(2) 0.0553(13) Uani 1 d . . .
H12A H 1.0206 -0.1528 0.2573 0.066 Uiso 1 calc . . R
H12B H 1.1398 0.0112 0.2306 0.066 Uiso 1 calc . . R
C13 C 0.7752(9) -0.0896(5) 0.1755(2) 0.0615(13) Uani 1 d . . .
H13A H 0.6077 -0.1628 0.1853 0.074 Uiso 1 calc . . R
H13B H 0.7109 0.0052 0.1609 0.074 Uiso 1 calc . . R
C14 C 0.9186(9) -0.1532(5) 0.1174(2) 0.0636(14) Uani 1 d . . .
H14A H 0.9927 -0.2446 0.1330 0.076 Uiso 1 calc . . R
H14B H 1.0800 -0.0774 0.1060 0.076 Uiso 1 calc . . R
C15 C 0.7249(9) -0.1947(6) 0.0529(2) 0.0654(14) Uani 1 d . . .
H15A H 0.5632 -0.2703 0.0643 0.078 Uiso 1 calc . . R
H15B H 0.6515 -0.1033 0.0371 0.078 Uiso 1 calc . . R
C16 C 0.8673(10) -0.2587(6) -0.0050(2) 0.0711(15) Uani 1 d . . .
H16A H 0.9574 -0.3437 0.0124 0.085 Uiso 1 calc . . R
H16B H 1.0175 -0.1792 -0.0191 0.085 Uiso 1 calc . . R
C17 C 0.6718(10) -0.3152(6) -0.0677(3) 0.0756(16) Uani 1 d . . .
H17A H 0.5167 -0.3914 -0.0533 0.091 Uiso 1 calc . . R
H17B H 0.5886 -0.2291 -0.0864 0.091 Uiso 1 calc . . R
C18 C 0.8136(12) -0.3852(7) -0.1237(3) 0.0905(18) Uani 1 d . . .
H18A H 0.9128 -0.4645 -0.1039 0.109 Uiso 1 calc . . R
H18B H 0.9565 -0.3060 -0.1411 0.109 Uiso 1 calc . . R
C19 C 0.6170(12) -0.4551(6) -0.1833(3) 0.106(2) Uani 1 d . . .
H19A H 0.7237 -0.5041 -0.2146 0.159 Uiso 1 calc . . GR
H19B H 0.5335 -0.3756 -0.2067 0.159 Uiso 1 calc . . GR
H19C H 0.4684 -0.5302 -0.1668 0.159 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.225(5) . ?
N1 C9 1.393(5) . ?
N1 C11 1.439(5) . ?
N1 C12 1.453(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C1 C3 1.393(5) 2_546 ?
C2 C3 1.404(5) . ?
C2 C6 1.478(5) . ?
C3 C1 1.393(5) 2_546 ?
C3 C4 1.496(6) . ?
C4 C5 1.473(5) . ?
C5 C6 1.391(5) . ?
C5 C10 1.381(5) . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.410(5) . ?
C9 C10 1.405(5) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.514(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.511(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.515(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.504(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.516(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.500(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.505(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C9 N1 C11 120.4(4) . . ?
C9 N1 C12 121.5(3) . . ?
C11 N1 C12 117.2(4) . . ?
C2 C1 H1 121.3 . . ?
C2 C1 C3 117.4(4) . 2_546 ?
C3 C1 H1 121.3 2_546 . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 C6 132.2(4) . . ?
C3 C2 C6 107.3(4) . . ?
C1 C3 C2 122.1(4) 2_546 . ?
C1 C3 C4 128.6(4) 2_546 . ?
C2 C3 C4 109.3(4) . . ?
O1 C4 C3 126.5(4) . . ?
O1 C4 C5 128.7(4) . . ?
C5 C4 C3 104.7(4) . . ?
C6 C5 C4 109.5(4) . . ?
C10 C5 C4 128.3(4) . . ?
C10 C5 C6 122.2(4) . . ?
C5 C6 C2 109.1(4) . . ?
C7 C6 C2 132.3(4) . . ?
C7 C6 C5 118.6(4) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.3(4) . . ?
C9 C8 H8 119.4 . . ?
N1 C9 C8 119.8(4) . . ?
N1 C9 C10 122.2(4) . . ?
C10 C9 C8 118.0(4) . . ?
C5 C10 C9 119.7(4) . . ?
C5 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 108.9 . . ?
N1 C12 H12B 108.9 . . ?
N1 C12 C13 113.4(3) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.8(4) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C13 C14 C15 114.4(4) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.4(4) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16A 108.4 . . ?
C15 C16 H16B 108.4 . . ?
C15 C16 C17 115.4(4) . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 C16 114.9(4) . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C17 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C17 C18 C19 115.5(5) . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C4 C5 C6 -178.8(4) . . . . ?
O1 C4 C5 C10 1.8(7) . . . . ?
N1 C9 C10 C5 177.5(4) . . . . ?
N1 C12 C13 C14 176.3(4) . . . . ?
C1 C2 C3 C1 0.8(7) . . . 2_546 ?
C1 C2 C3 C4 178.9(4) . . . . ?
C1 C2 C6 C5 -179.8(4) . . . . ?
C1 C2 C6 C7 0.7(8) . . . . ?
C1 C3 C4 O1 -2.3(8) 2_546 . . . ?
C1 C3 C4 C5 -179.9(4) 2_546 . . . ?
C2 C3 C4 O1 179.8(4) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C2 C6 C7 C8 179.0(4) . . . . ?
C3 C1 C2 C3 -0.8(7) 2_546 . . . ?
C3 C1 C2 C6 -179.3(4) 2_546 . . . ?
C3 C2 C6 C5 1.5(5) . . . . ?
C3 C2 C6 C7 -178.0(4) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C3 C4 C5 C10 179.4(4) . . . . ?
C4 C5 C6 C2 -0.1(5) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C4 C5 C10 C9 -178.5(4) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C6 C2 C3 C1 179.7(4) . . . 2_546 ?
C6 C2 C3 C4 -2.3(5) . . . . ?
C6 C5 C10 C9 2.2(6) . . . . ?
C6 C7 C8 C9 0.8(6) . . . . ?
C7 C8 C9 N1 -179.0(4) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C8 C9 C10 C5 -1.8(6) . . . . ?
C9 N1 C12 C13 83.1(5) . . . . ?
C10 C5 C6 C2 179.4(4) . . . . ?
C10 C5 C6 C7 -1.1(6) . . . . ?
C11 N1 C9 C8 -2.4(6) . . . . ?
C11 N1 C9 C10 178.4(4) . . . . ?
C11 N1 C12 C13 -85.6(5) . . . . ?
C12 N1 C9 C8 -170.7(4) . . . . ?
C12 N1 C9 C10 10.0(6) . . . . ?
C12 C13 C14 C15 176.8(4) . . . . ?
C13 C14 C15 C16 -179.8(4) . . . . ?
C14 C15 C16 C17 174.5(4) . . . . ?
C15 C16 C17 C18 -177.4(4) . . . . ?
C16 C17 C18 C19 174.5(4) . . . . ?

_olex2_date_sample_data_collection 2015-05-14
_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_fanzhp_0327
_database_code_depnum_ccdc_archive 'CCDC 2165711'
loop_
_audit_author_name
_audit_author_address
'Zhi-Ping Fan'
;Nanchang University
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H52 N2 O2'
_chemical_formula_sum            'C40 H52 N2 O2'
_chemical_formula_weight         592.83
_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                   7.472(2)
_cell_length_b                   8.150(2)
_cell_length_c                   15.418(4)
_cell_angle_alpha                93.63(2)
_cell_angle_beta                 93.79(2)
_cell_angle_gamma                110.48(3)
_cell_volume                     873.9(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    867
_cell_measurement_temperature    294.6(2)
_cell_measurement_theta_max      22.9050
_cell_measurement_theta_min      3.5830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             322
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5545
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.324
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  85.00   2.00   30.00    --   24.97  57.00 -30.00   40
  2  ω     42.00  82.00   2.00   30.00    --   24.97  57.00  30.00   20
  3  ω     13.00  93.00   2.00   30.00    --   24.97  38.00-120.00   40
  4  ω     22.00  62.00   2.00   30.00    --   24.97 -99.00-120.00   20
  5  ω    -12.00  28.00   2.00   30.00    --  -21.93 -99.00 -30.00   20
  6  ω    -13.00  27.00   2.00   30.00    --  -21.93 -99.00  30.00   20
  7  ω    -48.00  52.00   2.00   30.00    --   24.97 -57.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282201000
_diffrn_orient_matrix_UB_12      -0.0714179000
_diffrn_orient_matrix_UB_13      -0.0329033000
_diffrn_orient_matrix_UB_21      0.0968945000
_diffrn_orient_matrix_UB_22      0.0058902000
_diffrn_orient_matrix_UB_23      -0.0005334000
_diffrn_orient_matrix_UB_31      -0.0132440000
_diffrn_orient_matrix_UB_32      -0.0597556000
_diffrn_orient_matrix_UB_33      0.0325777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1795
_reflns_number_total             3343
_reflns_odcompleteness_completeness 97.67
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0820
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0875P)²+0.3655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1973
_refine_ls_wR_factor_ref         0.2445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19-C20
 1.45 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C17') \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C18)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H16A(0.55) H16B(0.55) H16C(0.45) H16D(0.45) H19C(0.45) H19D(0.45)
 H19A(0.55) H19B(0.55) C17(0.55) H17A(0.55) H17B(0.55) C18(0.55) H18A(0.55)
 H18B(0.55) C17'(0.45) H17C(0.45) H17D(0.45) C18'(0.45) H18C(0.45) H18D(0.45)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C16(H16C,H16D), C19(H19C,H19D), C19(H19A,H19B), C17(H17A,H17B),
 C18(H18A,H18B), C17'(H17C,H17D), C18'(H18C,H18D)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C)
;
_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
O1 O 0.3418(3) 0.7713(3) 0.06498(16) 0.0640(7) Uani 1 1 d . . . . .
N9 N -0.1793(4) 0.2178(4) 0.1948(2) 0.0670(9) Uani 1 1 d . . . . .
C1 C 0.1771(4) 0.7680(4) 0.0627(2) 0.0493(8) Uani 1 1 d . . . . .
C2 C 0.1014(4) 0.9010(4) 0.0274(2) 0.0477(8) Uani 1 1 d . . . . .
C3 C -0.0963(4) 0.8453(4) 0.0370(2) 0.0469(8) Uani 1 1 d . . . . .
C4 C -0.1530(4) 0.6782(4) 0.0788(2) 0.0470(8) Uani 1 1 d . . . . .
C5 C 0.0099(4) 0.6328(4) 0.0946(2) 0.0477(8) Uani 1 1 d . . . . .
C6 C 0.0048(5) 0.4836(4) 0.1335(2) 0.0550(9) Uani 1 1 d . . . . .
H6 H 0.116373 0.458653 0.143381 0.066 Uiso 1 1 calc R U . . .
C7 C -0.1691(5) 0.3700(4) 0.1580(2) 0.0550(9) Uani 1 1 d . . . . .
C8 C -0.3318(5) 0.4186(4) 0.1433(2) 0.0597(9) Uani 1 1 d . . . . .
H8 H -0.448203 0.347009 0.160751 0.072 Uiso 1 1 calc R U . . .
C9 C -0.3249(5) 0.5685(4) 0.1039(2) 0.0557(9) Uani 1 1 d . . . . .
H9 H -0.435458 0.595169 0.094484 0.067 Uiso 1 1 calc R U . . .
C10 C -0.2011(4) 0.9458(4) 0.0085(2) 0.0505(8) Uani 1 1 d . . . . .
H10 H -0.332276 0.911720 0.013306 0.061 Uiso 1 1 calc R U . . .
C11 C -0.0058(6) 0.1802(5) 0.2181(3) 0.0736(11) Uani 1 1 d . . . . .
H11A H 0.072041 0.199778 0.169172 0.088 Uiso 1 1 calc R U . . .
H11B H -0.042222 0.056965 0.228175 0.088 Uiso 1 1 calc R U . . .
C12 C 0.1134(7) 0.2898(6) 0.2977(3) 0.0996(15) Uani 1 1 d . . . . .
H12A H 0.151514 0.412127 0.288134 0.149 Uiso 1 1 calc R U . . .
H12B H 0.225509 0.259662 0.308670 0.149 Uiso 1 1 calc R U . . .
H12C H 0.039362 0.267776 0.347049 0.149 Uiso 1 1 calc R U . . .
C13 C -0.3617(5) 0.0804(5) 0.2044(3) 0.0696(11) Uani 1 1 d . . . . .
H13A H -0.349192 -0.032718 0.190727 0.084 Uiso 1 1 calc R U . . .
H13B H -0.457549 0.090585 0.161615 0.084 Uiso 1 1 calc R U . . .
C14 C -0.4341(6) 0.0816(5) 0.2927(3) 0.0841(13) Uani 1 1 d . . . . .
H14A H -0.445650 0.194731 0.307262 0.101 Uiso 1 1 calc R U . . .
H14B H -0.340997 0.067621 0.335721 0.101 Uiso 1 1 calc R U . . .
C15 C -0.6269(7) -0.0628(6) 0.2976(3) 0.0994(15) Uani 1 1 d . . . . .
H15A H -0.720596 -0.044278 0.256523 0.119 Uiso 1 1 calc R U . . .
H15B H -0.616448 -0.174757 0.279049 0.119 Uiso 1 1 calc R U . . .
C16 C -0.7003(10) -0.0743(8) 0.3852(4) 0.145(2) Uani 1 1 d . . . . .
H16A H -0.698624 0.039262 0.409118 0.174 Uiso 0.55 1 calc R U P A 1
H16B H -0.624522 -0.116485 0.425439 0.174 Uiso 0.55 1 calc R U P A 1
H16C H -0.586141 -0.041784 0.425849 0.174 Uiso 0.45 1 calc R U P B 2
H16D H -0.747103 0.022394 0.391676 0.174 Uiso 0.45 1 calc R U P B 2
C19 C -1.1976(15) -0.3904(14) 0.4249(7) 0.224(4) Uani 1 1 d D . . . .
H19C H -1.190410 -0.504725 0.408655 0.268 Uiso 0.45 1 calc R U P C 2
H19D H -1.188192 -0.368673 0.487889 0.268 Uiso 0.45 1 calc R U P C 2
H19A H -1.234856 -0.436404 0.480050 0.268 Uiso 0.55 1 calc R U P D 1
H19B H -1.174461 -0.482739 0.389767 0.268 Uiso 0.55 1 calc R U P D 1
C20 C -1.3607(14) -0.3668(13) 0.3827(7) 0.237(5) Uani 1 1 d D . . . .
H20A H -1.475399 -0.452753 0.399215 0.355 Uiso 1 1 calc R U . . .
H20B H -1.357779 -0.380862 0.320546 0.355 Uiso 1 1 calc R U . . .
H20C H -1.359085 -0.250937 0.399756 0.355 Uiso 1 1 calc R U . . .
C17 C -0.934(2) -0.2243(18) 0.3650(10) 0.108(4) Uani 0.55 1 d . U P E 1
H17A H -1.007936 -0.179281 0.325049 0.129 Uiso 0.55 1 calc R U P E 1
H17B H -0.933323 -0.334823 0.338107 0.129 Uiso 0.55 1 calc R U P E 1
C18 C -1.019(2) -0.252(2) 0.4432(10) 0.162(5) Uani 0.55 1 d . U P E 1
H18A H -1.037147 -0.145690 0.466365 0.195 Uiso 0.55 1 calc R U P E 1
H18B H -0.937851 -0.282626 0.486034 0.195 Uiso 0.55 1 calc R U P E 1
C17' C -0.833(2) -0.2097(18) 0.4202(10) 0.115(4) Uani 0.45 1 d . U P E 2
H17C H -0.826765 -0.186275 0.483014 0.138 Uiso 0.45 1 calc R U P E 2
H17D H -0.812245 -0.319424 0.407238 0.138 Uiso 0.45 1 calc R U P E 2
C18' C -1.029(3) -0.217(3) 0.3754(17) 0.143(8) Uani 0.45 1 d . U P E 2
H18C H -1.037733 -0.244723 0.312770 0.172 Uiso 0.45 1 calc R U P E 2
H18D H -1.049277 -0.107044 0.387131 0.172 Uiso 0.45 1 calc R U P E 2


_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 1.220(4) . ?
N9 C7 1.377(4) . ?
N9 C11 1.461(5) . ?
N9 C13 1.454(4) . ?
C1 C2 1.501(4) . ?
C1 C5 1.485(4) . ?
C2 C3 1.407(4) . ?
C2 C10 1.382(4) 2_575 ?
C3 C4 1.481(4) . ?
C3 C10 1.388(4) . ?
C4 C5 1.402(4) . ?
C4 C9 1.380(4) . ?
C5 C6 1.379(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.399(5) . ?
C7 C8 1.413(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.502(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.498(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.518(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.487(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C16 C17 1.742(15) . ?
C16 C17' 1.368(12) . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.422(5) . ?
C19 C18 1.412(15) . ?
C19 C18' 1.78(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.39(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C17' C18' 1.56(2) . ?
C18' H18C 0.9700 . ?
C18' H18D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N9 C11 120.9(3) . . ?
C7 N9 C13 121.9(3) . . ?
C13 N9 C11 116.9(3) . . ?
O1 C1 C2 127.1(3) . . ?
O1 C1 C5 127.3(3) . . ?
C5 C1 C2 105.6(3) . . ?
C3 C2 C1 108.2(3) . . ?
C10 C2 C1 128.3(3) 2_575 . ?
C10 C2 C3 123.5(3) 2_575 . ?
C2 C3 C4 108.7(3) . . ?
C10 C3 C2 119.6(3) . . ?
C10 C3 C4 131.8(3) . . ?
C5 C4 C3 108.6(3) . . ?
C9 C4 C3 133.3(3) . . ?
C9 C4 C5 118.1(3) . . ?
C4 C5 C1 108.9(3) . . ?
C6 C5 C1 128.2(3) . . ?
C6 C5 C4 122.8(3) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
N9 C7 C6 120.8(3) . . ?
N9 C7 C8 122.0(3) . . ?
C6 C7 C8 117.2(3) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.7 . . ?
C4 C9 C8 119.7(3) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C2 C10 C3 116.9(3) 2_575 . ?
C2 C10 H10 121.6 2_575 . ?
C3 C10 H10 121.6 . . ?
N9 C11 H11A 108.8 . . ?
N9 C11 H11B 108.8 . . ?
N9 C11 C12 113.9(3) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N9 C13 H13A 108.4 . . ?
N9 C13 H13B 108.4 . . ?
N9 C13 C14 115.7(3) . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 113.0(4) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 C14 115.2(5) . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
C15 C16 H16C 104.5 . . ?
C15 C16 H16D 104.5 . . ?
C15 C16 C17 103.6(7) . . ?
H16A C16 H16B 109.0 . . ?
H16C C16 H16D 105.6 . . ?
C17 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
C17' C16 C15 131.1(8) . . ?
C17' C16 H16C 104.5 . . ?
C17' C16 H16D 104.5 . . ?
H19C C19 H19D 110.3 . . ?
H19A C19 H19B 106.6 . . ?
C20 C19 H19C 112.9 . . ?
C20 C19 H19D 112.9 . . ?
C20 C19 H19A 106.7 . . ?
C20 C19 H19B 106.7 . . ?
C20 C19 C18' 94.3(10) . . ?
C18 C19 H19A 106.7 . . ?
C18 C19 H19B 106.7 . . ?
C18 C19 C20 122.5(11) . . ?
C18' C19 H19C 112.9 . . ?
C18' C19 H19D 112.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 C16 109.5(13) . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C17 C18 C19 107.0(13) . . ?
C17 C18 H18A 110.3 . . ?
C17 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
C16 C17' H17C 110.9 . . ?
C16 C17' H17D 110.9 . . ?
C16 C17' C18' 104.2(14) . . ?
H17C C17' H17D 108.9 . . ?
C18' C17' H17C 110.9 . . ?
C18' C17' H17D 110.9 . . ?
C19 C18' H18C 111.2 . . ?
C19 C18' H18D 111.2 . . ?
C17' C18' C19 102.8(14) . . ?
C17' C18' H18C 111.2 . . ?
C17' C18' H18D 111.2 . . ?
H18C C18' H18D 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.6(3) . . . . ?
O1 C1 C2 C10 -0.9(6) . . . 2_575 ?
O1 C1 C5 C4 -179.5(3) . . . . ?
O1 C1 C5 C6 0.1(6) . . . . ?
N9 C7 C8 C9 -178.0(3) . . . . ?
N9 C13 C14 C15 178.8(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C10 -179.5(3) . . . . ?
C1 C5 C6 C7 -178.9(3) . . . . ?
C2 C1 C5 C4 0.9(4) . . . . ?
C2 C1 C5 C6 -179.5(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C9 179.3(4) . . . . ?
C2 C3 C10 C2 -0.8(5) . . . 2_575 ?
C3 C4 C5 C1 -0.6(4) . . . . ?
C3 C4 C5 C6 179.7(3) . . . . ?
C3 C4 C9 C8 -179.3(3) . . . . ?
C4 C3 C10 C2 179.2(3) . . . 2_575 ?
C4 C5 C6 C7 0.6(5) . . . . ?
C5 C1 C2 C3 -0.8(3) . . . . ?
C5 C1 C2 C10 178.7(3) . . . 2_575 ?
C5 C4 C9 C8 -0.2(5) . . . . ?
C5 C6 C7 N9 178.3(3) . . . . ?
C5 C6 C7 C8 -1.8(5) . . . . ?
C6 C7 C8 C9 2.0(5) . . . . ?
C7 N9 C11 C12 73.4(5) . . . . ?
C7 N9 C13 C14 -98.3(4) . . . . ?
C7 C8 C9 C4 -1.1(5) . . . . ?
C9 C4 C5 C1 -180.0(3) . . . . ?
C9 C4 C5 C6 0.4(5) . . . . ?
C10 C2 C3 C4 -179.1(3) 2_575 . . . ?
C10 C2 C3 C10 0.9(5) 2_575 . . . ?
C10 C3 C4 C5 -179.9(3) . . . . ?
C10 C3 C4 C9 -0.7(6) . . . . ?
C11 N9 C7 C6 6.8(5) . . . . ?
C11 N9 C7 C8 -173.2(3) . . . . ?
C11 N9 C13 C14 87.6(4) . . . . ?
C13 N9 C7 C6 -167.2(3) . . . . ?
C13 N9 C7 C8 12.9(5) . . . . ?
C13 N9 C11 C12 -112.3(4) . . . . ?
C13 C14 C15 C16 176.6(4) . . . . ?
C14 C15 C16 C17 170.8(6) . . . . ?
C14 C15 C16 C17' -159.0(10) . . . . ?
C15 C16 C17 C18 178.2(12) . . . . ?
C15 C16 C17' C18' -74.7(16) . . . . ?
C16 C17 C18 C19 -172.4(10) . . . . ?
C16 C17' C18' C19 -178.4(11) . . . . ?
C20 C19 C18 C17 -76.4(19) . . . . ?
C20 C19 C18' C17' 175.4(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.664
####################################################################### 
# 
# 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_eoaifd
_database_code_depnum_ccdc_archive 'CCDC 2165712'
loop_
_audit_author_name
_audit_author_address
'Zhi-Ping Fan'
;Nanchang University
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H52 N2 O2'
_chemical_formula_sum            'C40 H52 N2 O2'
_chemical_formula_weight         592.83
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.4361(3)
_cell_length_b                   9.5906(4)
_cell_length_c                   12.8654(5)
_cell_angle_alpha                77.045(2)
_cell_angle_beta                 85.845(2)
_cell_angle_gamma                70.851(2)
_cell_volume                     844.69(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    630
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      20.3080
_cell_measurement_theta_min      4.1830
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6647
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.623
_diffrn_reflns_theta_max         66.623
_diffrn_reflns_theta_min         4.996
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2677
_reflns_number_total             2930
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.956
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.028
_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)+(0.0799P)²+0.3664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1538
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.35358(15) 0.21261(13) 0.42331(9) 0.0308(3) Uani 1 1 d . . . . .
C1 C 0.8395(2) 0.62346(18) 0.35029(12) 0.0275(4) Uani 1 1 d . . . . .
N1 N 0.83299(19) 0.77231(15) 0.31994(12) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.6776(2) 0.43212(19) 0.40602(13) 0.0286(4) Uani 1 1 d . . . . .
H3 H 0.562556 0.408266 0.418893 0.034 Uiso 1 1 calc R U . . .
C2 C 0.6727(2) 0.58120(19) 0.36966(13) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.552466 0.657889 0.357303 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8519(2) 0.31858(18) 0.42332(12) 0.0248(4) Uani 1 1 d . . . . .
C5 C 1.0180(2) 0.35947(18) 0.40300(12) 0.0255(4) Uani 1 1 d . . . . .
C6 C 1.0164(2) 0.50545(19) 0.36656(13) 0.0278(4) Uani 1 1 d . . . . .
H6 H 1.132544 0.527411 0.352328 0.033 Uiso 1 1 calc R U . . .
C7 C 1.1860(2) 0.22081(18) 0.43043(12) 0.0250(4) Uani 1 1 d . . . . .
C9 C 0.9062(2) 0.15382(18) 0.46291(12) 0.0245(4) Uani 1 1 d . . . . .
C8 C 1.1066(2) 0.09352(18) 0.46851(12) 0.0245(4) Uani 1 1 d . . . . .
C10 C 1.2035(2) -0.05855(17) 0.50519(12) 0.0247(4) Uani 1 1 d . . . . .
H10 H 1.338573 -0.096129 0.508427 0.030 Uiso 1 1 calc R U . . .
C11 C 1.0048(2) 0.81052(19) 0.28453(14) 0.0332(4) Uani 1 1 d . . . . .
H11A H 1.106928 0.751965 0.337507 0.040 Uiso 1 1 calc R U . . .
H11B H 0.979622 0.918972 0.282870 0.040 Uiso 1 1 calc R U . . .
C12 C 1.0761(3) 0.7801(2) 0.17506(15) 0.0420(5) Uani 1 1 d . . . . .
H12A H 1.196549 0.801460 0.159401 0.063 Uiso 1 1 calc R U . . .
H12B H 0.981522 0.845303 0.120756 0.063 Uiso 1 1 calc R U . . .
H12C H 1.096040 0.674036 0.174640 0.063 Uiso 1 1 calc R U . . .
C13 C 0.6520(2) 0.89467(19) 0.30680(13) 0.0309(4) Uani 1 1 d . . . . .
H13A H 0.673488 0.986183 0.319262 0.037 Uiso 1 1 calc R U . . .
H13B H 0.563557 0.867017 0.362657 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5551(2) 0.9345(2) 0.19849(14) 0.0344(4) Uani 1 1 d . . . . .
H14A H 0.535801 0.843511 0.183669 0.041 Uiso 1 1 calc R U . . .
H14B H 0.638080 0.969055 0.141956 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3631(2) 1.0588(2) 0.19666(14) 0.0346(4) Uani 1 1 d . . . . .
H15A H 0.271639 1.015551 0.240702 0.042 Uiso 1 1 calc R U . . .
H15B H 0.378458 1.138164 0.229612 0.042 Uiso 1 1 calc R U . . .
C16 C 0.2799(3) 1.1317(2) 0.08487(14) 0.0381(4) Uani 1 1 d . . . . .
H16A H 0.380415 1.156913 0.037155 0.046 Uiso 1 1 calc R U . . .
H16B H 0.241115 1.057185 0.057461 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1087(3) 1.2745(2) 0.08015(15) 0.0392(4) Uani 1 1 d . . . . .
H17A H 0.142282 1.342299 0.117491 0.047 Uiso 1 1 calc R U . . .
H17B H 0.083802 1.327200 0.004546 0.047 Uiso 1 1 calc R U . . .
C18 C -0.0739(3) 1.2495(2) 0.12855(15) 0.0397(4) Uani 1 1 d . . . . .
H18A H -0.050994 1.198298 0.204543 0.048 Uiso 1 1 calc R U . . .
H18B H -0.108931 1.182058 0.091540 0.048 Uiso 1 1 calc R U . . .
C19 C -0.2389(3) 1.3960(2) 0.12065(18) 0.0460(5) Uani 1 1 d . . . . .
H19A H -0.209451 1.458283 0.164624 0.055 Uiso 1 1 calc R U . . .
H19B H -0.251299 1.452908 0.045692 0.055 Uiso 1 1 calc R U . . .
C20 C -0.4272(3) 1.3730(3) 0.1566(2) 0.0591(6) Uani 1 1 d . . . . .
H20A H -0.524575 1.471355 0.155336 0.089 Uiso 1 1 calc R U . . .
H20B H -0.414346 1.311582 0.229326 0.089 Uiso 1 1 calc R U . . .
H20C H -0.464700 1.321321 0.108514 0.089 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 C7 1.2203(19) . ?
C1 N1 1.378(2) . ?
C1 C2 1.416(2) . ?
C1 C6 1.418(2) . ?
N1 C11 1.457(2) . ?
N1 C13 1.458(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.390(2) . ?
C3 C4 1.386(2) . ?
C2 H2 0.9500 . ?
C4 C5 1.405(2) . ?
C4 C9 1.473(2) . ?
C5 C6 1.370(2) . ?
C5 C7 1.489(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.497(2) . ?
C9 C8 1.411(2) . ?
C9 C10 1.393(2) 2_756 ?
C8 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.525(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.527(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.528(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.527(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.521(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.521(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.512(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.22(14) . . ?
N1 C1 C6 120.74(15) . . ?
C2 C1 C6 117.02(15) . . ?
C1 N1 C11 120.49(13) . . ?
C1 N1 C13 121.17(14) . . ?
C11 N1 C13 117.70(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.41(15) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.72(15) . . ?
C3 C2 H2 118.6 . . ?
C3 C4 C5 118.18(15) . . ?
C3 C4 C9 133.00(14) . . ?
C5 C4 C9 108.80(13) . . ?
C4 C5 C7 108.65(14) . . ?
C6 C5 C4 123.37(14) . . ?
C6 C5 C7 127.96(14) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.26(15) . . ?
C5 C6 H6 120.4 . . ?
O1 C7 C5 127.18(15) . . ?
O1 C7 C8 127.17(14) . . ?
C5 C7 C8 105.65(12) . . ?
C8 C9 C4 108.77(13) . . ?
C10 C9 C4 131.41(14) 2_756 . ?
C10 C9 C8 119.80(15) 2_756 . ?
C9 C8 C7 108.12(13) . . ?
C10 C8 C7 128.66(14) . . ?
C10 C8 C9 123.22(15) . . ?
C9 C10 H10 121.5 2_756 . ?
C8 C10 C9 116.98(14) . 2_756 ?
C8 C10 H10 121.5 . . ?
N1 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
N1 C11 C12 114.46(14) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 108.3 . . ?
N1 C13 H13B 108.3 . . ?
N1 C13 C14 115.87(14) . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 C15 110.77(14) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.81(14) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.93(15) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 108.4 . . ?
C16 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 C16 115.39(16) . . ?
C18 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C17 C18 C19 112.73(16) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.72(18) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C7 C8 C9 -179.59(15) . . . . ?
O1 C7 C8 C10 1.2(3) . . . . ?
C1 N1 C11 C12 71.8(2) . . . . ?
C1 N1 C13 C14 -84.8(2) . . . . ?
N1 C1 C2 C3 -176.32(15) . . . . ?
N1 C1 C6 C5 176.02(14) . . . . ?
N1 C13 C14 C15 177.33(14) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C7 178.16(13) . . . . ?
C3 C4 C9 C8 -177.65(16) . . . . ?
C3 C4 C9 C10 0.9(3) . . . 2_756 ?
C2 C1 N1 C11 -170.25(15) . . . . ?
C2 C1 N1 C13 0.4(2) . . . . ?
C2 C1 C6 C5 -2.2(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C9 178.37(16) . . . . ?
C4 C3 C2 C1 -0.7(3) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C4 C5 C7 O1 -179.85(15) . . . . ?
C4 C5 C7 C8 0.17(16) . . . . ?
C4 C9 C8 C7 -0.78(17) . . . . ?
C4 C9 C8 C10 178.47(14) . . . . ?
C5 C4 C9 C8 0.91(17) . . . . ?
C5 C4 C9 C10 179.46(15) . . . 2_756 ?
C5 C7 C8 C9 0.39(16) . . . . ?
C5 C7 C8 C10 -178.81(15) . . . . ?
C6 C1 N1 C11 11.6(2) . . . . ?
C6 C1 N1 C13 -177.74(14) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
C6 C5 C7 O1 -1.5(3) . . . . ?
C6 C5 C7 C8 178.57(15) . . . . ?
C7 C5 C6 C1 -176.68(14) . . . . ?
C7 C8 C10 C9 179.36(14) . . . 2_756 ?
C9 C4 C5 C6 -179.14(14) . . . . ?
C9 C4 C5 C7 -0.65(17) . . . . ?
C9 C8 C10 C9 0.3(2) . . . 2_756 ?
C10 C9 C8 C7 -179.53(13) 2_756 . . . ?
C10 C9 C8 C10 -0.3(3) 2_756 . . . ?
C11 N1 C13 C14 86.10(19) . . . . ?
C13 N1 C11 C12 -99.17(18) . . . . ?
C13 C14 C15 C16 165.94(15) . . . . ?
C14 C15 C16 C17 -169.03(15) . . . . ?
C15 C16 C17 C18 -71.8(2) . . . . ?
C16 C17 C18 C19 -179.64(16) . . . . ?
C17 C18 C19 C20 173.36(18) . . . . ?

_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_fanzhp_4-8
_database_code_depnum_ccdc_archive 'CCDC 2165714'
loop_
_audit_author_name
_audit_author_address
'Zhi-Ping Fan'
;Nanchang University
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 N O'
_chemical_formula_sum            'C22 H28 N O'
_chemical_formula_weight         322.45
_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/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                   22.086(5)
_cell_length_b                   8.6264(12)
_cell_length_c                   9.989(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.695(18)
_cell_angle_gamma                90
_cell_volume                     1881.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.3080
_cell_measurement_theta_min      4.1830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_unetI/netI     0.1954
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6580
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.360
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_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                1415
_reflns_number_total             3705
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.2483
_refine_ls_R_factor_gt           0.1209
_refine_ls_restrained_S_all      1.032
_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)+(0.1877P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2963
_refine_ls_wR_factor_ref         0.4115
_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 Secondary CH2 refined with riding coordinates:
 C00D(H00D,H00E), C00E(H00F,H00G), C00F(H00H,H00I), C00G(H00J,H00K), C00H(H00L,
 H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00B(H00B), C00C(H00C), C00I(H00N), C(H), C3(H3),
 C4(H4), C8(H8)
2.c Idealised Me refined as rotating group:
 C00J(H00O,H00P,H00Q), C2(H2A,H2B,H2C)
;
_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 0.10294(18) 0.6400(4) 0.7570(4) 0.0475(12) Uani 1 1 d . . . . .
N1 N 0.17624(19) 0.0666(5) 0.6139(4) 0.0361(12) Uani 1 1 d . . . . .
C23 C 0.0145(2) 0.6555(6) 0.9694(6) 0.0339(13) Uani 1 1 d . . . . .
H23 H 0.024585 0.756367 0.948216 0.041 Uiso 1 1 calc R U . . .
C24 C 0.0391(2) 0.5291(6) 0.9113(5) 0.0324(14) Uani 1 1 d . . . . .
C3 C 0.0814(2) 0.5297(6) 0.8091(5) 0.0336(14) Uani 1 1 d . . . . .
C4 C 0.0932(2) 0.3610(6) 0.7817(5) 0.0267(13) Uani 1 1 d . . . . .
C5 C 0.0609(2) 0.2725(6) 0.8612(5) 0.0274(12) Uani 1 1 d . . . . .
C6 C 0.0252(2) 0.3734(6) 0.9410(5) 0.0301(13) Uani 1 1 d . . . . .
C7 C 0.0682(2) 0.1119(6) 0.8621(5) 0.0335(13) Uani 1 1 d . . . . .
H7 H 0.047316 0.050138 0.916270 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1069(2) 0.0454(6) 0.7819(5) 0.0334(13) Uani 1 1 d . . . . .
H8 H 0.111647 -0.061683 0.783281 0.040 Uiso 1 1 calc R U . . .
C9 C 0.1396(2) 0.1349(6) 0.6973(6) 0.0321(13) Uani 1 1 d . . . . .
C10 C 0.1319(2) 0.2972(6) 0.7005(6) 0.0376(14) Uani 1 1 d . . . . .
H10 H 0.152865 0.360963 0.648024 0.045 Uiso 1 1 calc R U . . .
C11 C 0.1893(2) -0.0998(6) 0.6213(6) 0.0387(14) Uani 1 1 d . . . . .
H11A H 0.202563 -0.132310 0.537388 0.046 Uiso 1 1 calc R U . . .
H11B H 0.151809 -0.155139 0.629509 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2382(3) -0.1447(6) 0.7393(7) 0.0474(17) Uani 1 1 d . . . . .
H12A H 0.223514 -0.120676 0.823646 0.057 Uiso 1 1 calc R U . . .
H12B H 0.274688 -0.083270 0.735502 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2549(3) -0.3166(7) 0.7381(7) 0.0553(18) Uani 1 1 d . . . . .
H13A H 0.267786 -0.342253 0.652178 0.066 Uiso 1 1 calc R U . . .
H13B H 0.219064 -0.378444 0.747078 0.066 Uiso 1 1 calc R U . . .
C14 C 0.3070(3) -0.3570(8) 0.8547(8) 0.071(2) Uani 1 1 d . . . . .
H14A H 0.318936 -0.463208 0.846588 0.106 Uiso 1 1 calc R U . . .
H14B H 0.292833 -0.342175 0.940084 0.106 Uiso 1 1 calc R U . . .
H14C H 0.341517 -0.290768 0.849888 0.106 Uiso 1 1 calc R U . . .
C15 C 0.2111(2) 0.1596(6) 0.5310(6) 0.0382(15) Uani 1 1 d . . . . .
H15A H 0.185806 0.246363 0.495109 0.046 Uiso 1 1 calc R U . . .
H15B H 0.218818 0.097054 0.454699 0.046 Uiso 1 1 calc R U . . .
C16 C 0.2724(3) 0.2234(7) 0.6012(6) 0.0468(16) Uani 1 1 d . . . . .
H16A H 0.265491 0.285474 0.678471 0.056 Uiso 1 1 calc R U . . .
H16B H 0.298885 0.137695 0.634472 0.056 Uiso 1 1 calc R U . . .
C17 C 0.3038(3) 0.3211(7) 0.5073(7) 0.0549(18) Uani 1 1 d . . . . .
H17A H 0.307519 0.259440 0.427765 0.066 Uiso 1 1 calc R U . . .
H17B H 0.277173 0.407904 0.477639 0.066 Uiso 1 1 calc R U . . .
C18 C 0.3641(5) 0.3825(14) 0.5598(11) 0.126(4) Uani 1 1 d . U . . .
H18 H 0.372897 0.478746 0.525506 0.151 Uiso 1 1 calc R U . . .
C19 C 0.4040(7) 0.3281(18) 0.6404(17) 0.183(6) Uani 1 1 d . U . . .
H19 H 0.394226 0.236342 0.681020 0.220 Uiso 1 1 calc R U . . .
C20 C 0.4716(7) 0.391(2) 0.6877(18) 0.207(6) Uani 1 1 d . U . . .
H20A H 0.493229 0.375158 0.611259 0.248 Uiso 1 1 calc R U . . .
H20B H 0.467572 0.502103 0.697241 0.248 Uiso 1 1 calc R U . . .
C21 C 0.5105(11) 0.344(2) 0.798(2) 0.252(9) Uani 1 1 d . U . . .
H21A H 0.511072 0.232016 0.792132 0.303 Uiso 1 1 calc R U . . .
H21B H 0.489925 0.368552 0.874408 0.303 Uiso 1 1 calc R U . . .
C22 C 0.5723(6) 0.387(2) 0.8392(15) 0.203(6) Uani 1 1 d . U . . .
H22A H 0.597891 0.334719 0.784159 0.305 Uiso 1 1 calc R U . . .
H22B H 0.584508 0.359417 0.932385 0.305 Uiso 1 1 calc R U . . .
H22C H 0.576504 0.497385 0.829078 0.305 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 C3 1.216(6) . ?
N1 C9 1.379(6) . ?
N1 C11 1.463(6) . ?
N1 C15 1.454(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(7) . ?
C23 C6 1.368(7) 3_567 ?
C24 C3 1.484(8) . ?
C24 C6 1.419(7) . ?
C3 C4 1.510(7) . ?
C4 C5 1.376(7) . ?
C4 C10 1.379(7) . ?
C5 C6 1.484(7) . ?
C5 C7 1.395(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.420(7) . ?
C9 C10 1.411(7) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.524(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.529(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.548(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.530(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.506(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.456(11) . ?
C18 H18 0.9300 . ?
C18 C19 1.197(15) . ?
C19 H19 0.9300 . ?
C19 C20 1.590(17) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.35(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.41(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C9 N1 C11 121.2(5) . . ?
C9 N1 C15 121.2(4) . . ?
C15 N1 C11 116.9(4) . . ?
C24 C23 H23 121.2 . . ?
C6 C23 H23 121.2 3_567 . ?
C6 C23 C24 117.5(5) 3_567 . ?
C23 C24 C3 127.8(5) . . ?
C23 C24 C6 123.2(5) . . ?
C6 C24 C3 109.0(5) . . ?
O1 C3 C24 128.7(5) . . ?
O1 C3 C4 126.0(5) . . ?
C24 C3 C4 105.4(4) . . ?
C5 C4 C3 108.2(5) . . ?
C5 C4 C10 122.7(5) . . ?
C10 C4 C3 129.0(5) . . ?
C4 C5 C6 110.3(4) . . ?
C4 C5 C7 119.0(5) . . ?
C7 C5 C6 130.5(5) . . ?
C23 C6 C24 119.3(5) 3_567 . ?
C23 C6 C5 133.6(5) 3_567 . ?
C24 C6 C5 107.1(5) . . ?
C5 C7 H7 120.3 . . ?
C8 C7 C5 119.3(5) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.3(5) . . ?
C9 C8 H8 118.8 . . ?
N1 C9 C8 121.7(5) . . ?
N1 C9 C10 121.5(5) . . ?
C10 C9 C8 116.8(5) . . ?
C4 C10 C9 119.8(5) . . ?
C4 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
N1 C11 C12 113.6(4) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C11 C12 C13 112.6(5) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.4(5) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 108.2 . . ?
N1 C15 H15B 108.2 . . ?
N1 C15 C16 116.5(4) . . ?
H15A C15 H15B 107.3 . . ?
C16 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 112.0(5) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 107.9 . . ?
C16 C17 H17B 107.9 . . ?
H17A C17 H17B 107.2 . . ?
C18 C17 C16 117.5(6) . . ?
C18 C17 H17A 107.9 . . ?
C18 C17 H17B 107.9 . . ?
C17 C18 H18 115.1 . . ?
C19 C18 C17 129.9(12) . . ?
C19 C18 H18 115.1 . . ?
C18 C19 H19 115.5 . . ?
C18 C19 C20 129.0(16) . . ?
C20 C19 H19 115.5 . . ?
C19 C20 H20A 105.7 . . ?
C19 C20 H20B 105.7 . . ?
H20A C20 H20B 106.1 . . ?
C21 C20 C19 126.5(18) . . ?
C21 C20 H20A 105.7 . . ?
C21 C20 H20B 105.7 . . ?
C20 C21 H21A 105.1 . . ?
C20 C21 H21B 105.1 . . ?
C20 C21 C22 129(2) . . ?
H21A C21 H21B 105.9 . . ?
C22 C21 H21A 105.1 . . ?
C22 C21 H21B 105.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 C3 C4 C5 179.5(5) . . . . ?
O1 C3 C4 C10 3.7(8) . . . . ?
N1 C9 C10 C4 177.7(4) . . . . ?
N1 C11 C12 C13 -175.2(5) . . . . ?
N1 C15 C16 C17 -178.5(5) . . . . ?
C23 C24 C3 O1 0.5(9) . . . . ?
C23 C24 C3 C4 -179.8(5) . . . . ?
C23 C24 C6 C23 0.3(8) . . . 3_567 ?
C23 C24 C6 C5 -179.2(4) . . . . ?
C24 C3 C4 C5 -0.2(5) . . . . ?
C24 C3 C4 C10 -176.0(5) . . . . ?
C3 C24 C6 C23 -178.3(4) . . . 3_567 ?
C3 C24 C6 C5 2.2(5) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C3 C4 C5 C7 -174.9(4) . . . . ?
C3 C4 C10 C9 175.1(5) . . . . ?
C4 C5 C6 C23 178.2(5) . . . 3_567 ?
C4 C5 C6 C24 -2.4(5) . . . . ?
C4 C5 C7 C8 -1.0(6) . . . . ?
C5 C4 C10 C9 -0.2(7) . . . . ?
C5 C7 C8 C9 -0.2(7) . . . . ?
C6 C23 C24 C3 178.0(5) 3_567 . . . ?
C6 C23 C24 C6 -0.3(8) 3_567 . . . ?
C6 C24 C3 O1 179.0(5) . . . . ?
C6 C24 C3 C4 -1.3(5) . . . . ?
C6 C5 C7 C8 -176.7(5) . . . . ?
C7 C5 C6 C23 -5.9(9) . . . 3_567 ?
C7 C5 C6 C24 173.5(5) . . . . ?
C7 C8 C9 N1 -177.5(4) . . . . ?
C7 C8 C9 C10 1.2(7) . . . . ?
C8 C9 C10 C4 -1.1(7) . . . . ?
C9 N1 C11 C12 -78.7(6) . . . . ?
C9 N1 C15 C16 82.3(6) . . . . ?
C10 C4 C5 C6 177.7(4) . . . . ?
C10 C4 C5 C7 1.2(7) . . . . ?
C11 N1 C9 C8 -7.9(7) . . . . ?
C11 N1 C9 C10 173.4(4) . . . . ?
C11 N1 C15 C16 -88.1(6) . . . . ?
C11 C12 C13 C14 177.1(5) . . . . ?
C15 N1 C9 C8 -177.9(4) . . . . ?
C15 N1 C9 C10 3.3(7) . . . . ?
C15 N1 C11 C12 91.8(6) . . . . ?
C15 C16 C17 C18 -177.0(7) . . . . ?
C16 C17 C18 C19 33(2) . . . . ?
C17 C18 C19 C20 174.6(13) . . . . ?
C18 C19 C20 C21 165(2) . . . . ?
C19 C20 C21 C22 174.9(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
