# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_WF-1
_database_code_depnum_ccdc_archive 'CCDC 2298879'
loop_
_audit_author_name
_audit_author_address
'Qing He'
;Hunan University
China
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 N3 O2'
_chemical_formula_weight         365.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.9704(2)
_cell_length_b                   14.6873(4)
_cell_length_c                   14.7777(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.7410(10)
_cell_angle_gamma                90
_cell_volume                     1929.23(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    25737
_cell_measurement_theta_min      4.263
_cell_measurement_theta_max      68.211

_exptl_crystal_description       block
_exptl_crystal_colour            yellowish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.647
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microfocus Source'
_diffrn_measurement_device_type  'Bruker D8 Venture with PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28890
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.263
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3520
_reflns_number_gt                3129
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_cell_refinement       'SAINT V8.37A Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.37A Bruker-AXS, Madison WI'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
Bruker SHELXTL Bruker-AXS, Madison WI and local programs
;
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.7889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3520
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.16104(12) 0.47008(7) 0.42625(7) 0.0359(3) Uani 1 1 d . . . . .
O2 O 0.64373(11) 0.59471(7) 0.52967(6) 0.0335(2) Uani 1 1 d . . . . .
N1 N 0.01137(12) 0.35084(7) 0.55515(7) 0.0246(2) Uani 1 1 d . . . . .
H1 H 0.068101 0.397067 0.543323 0.030 Uiso 1 1 calc R U . . .
N2 N 0.31601(12) 0.33420(7) 0.64538(7) 0.0245(2) Uani 1 1 d . . . . .
H2 H 0.310642 0.367835 0.595767 0.029 Uiso 1 1 calc R U . . .
N3 N 0.57172(12) 0.44820(7) 0.64028(7) 0.0247(2) Uani 1 1 d . . . . .
H3 H 0.493397 0.463365 0.600723 0.030 Uiso 1 1 calc R U . . .
C1 C -0.21381(16) 0.39900(9) 0.45360(9) 0.0273(3) Uani 1 1 d . . . . .
H1A H -0.315637 0.385281 0.431294 0.033 Uiso 1 1 calc R U . . .
C2 C -0.13497(15) 0.33623(9) 0.51551(9) 0.0243(3) Uani 1 1 d . . . . .
C3 C -0.18436(15) 0.25511(9) 0.55143(9) 0.0257(3) Uani 1 1 d . . . . .
C4 C -0.06587(15) 0.22092(9) 0.61416(9) 0.0250(3) Uani 1 1 d . . . . .
C5 C 0.05431(15) 0.28247(9) 0.61548(9) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.20107(15) 0.28204(9) 0.66944(9) 0.0245(3) Uani 1 1 d . . . . .
C7 C 0.25469(16) 0.23984(10) 0.75106(10) 0.0319(3) Uani 1 1 d . . . . .
H7 H 0.200086 0.198957 0.784046 0.038 Uiso 1 1 calc R U . . .
C8 C 0.40368(16) 0.26800(10) 0.77653(10) 0.0312(3) Uani 1 1 d . . . . .
H8 H 0.467643 0.250076 0.830085 0.037 Uiso 1 1 calc R U . . .
C9 C 0.44097(15) 0.32648(9) 0.70984(9) 0.0240(3) Uani 1 1 d . . . . .
C10 C 0.57427(14) 0.37988(9) 0.70240(8) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.71892(15) 0.37707(9) 0.75294(9) 0.0239(3) Uani 1 1 d . . . . .
C12 C 0.80416(14) 0.44606(9) 0.71874(8) 0.0236(3) Uani 1 1 d . . . . .
C13 C 0.71050(14) 0.49028(9) 0.64855(9) 0.0242(3) Uani 1 1 d . . . . .
C14 C 0.73828(15) 0.56303(10) 0.59106(9) 0.0273(3) Uani 1 1 d . . . . .
H14 H 0.835620 0.589724 0.599655 0.033 Uiso 1 1 calc R U . . .
C15 C -0.33546(15) 0.21127(10) 0.52497(10) 0.0326(3) Uani 1 1 d . . . . .
H15A H -0.403626 0.255350 0.489605 0.039 Uiso 1 1 calc R U . . .
H15B H -0.379311 0.195553 0.580954 0.039 Uiso 1 1 calc R U . . .
C16 C -0.32526(19) 0.12548(11) 0.46809(11) 0.0418(4) Uani 1 1 d . . . . .
H16A H -0.285755 0.141109 0.411391 0.063 Uiso 1 1 calc R U . . .
H16B H -0.425583 0.098563 0.453492 0.063 Uiso 1 1 calc R U . . .
H16C H -0.257886 0.081605 0.502827 0.063 Uiso 1 1 calc R U . . .
C17 C -0.06476(16) 0.13391(9) 0.66793(10) 0.0306(3) Uani 1 1 d . . . . .
H17A H -0.168594 0.109727 0.662610 0.037 Uiso 1 1 calc R U . . .
H17B H -0.031723 0.147444 0.733175 0.037 Uiso 1 1 calc R U . . .
C18 C 0.03811(19) 0.06073(10) 0.63646(12) 0.0424(4) Uani 1 1 d . . . . .
H18A H 0.002981 0.044520 0.572824 0.064 Uiso 1 1 calc R U . . .
H18B H 0.036100 0.006638 0.675097 0.064 Uiso 1 1 calc R U . . .
H18C H 0.141180 0.084145 0.641279 0.064 Uiso 1 1 calc R U . . .
C19 C 0.77173(16) 0.31094(10) 0.82847(9) 0.0299(3) Uani 1 1 d . . . . .
H19A H 0.881608 0.302175 0.830784 0.036 Uiso 1 1 calc R U . . .
H19B H 0.722744 0.251359 0.813805 0.036 Uiso 1 1 calc R U . . .
C20 C 0.73855(19) 0.34122(11) 0.92269(10) 0.0390(4) Uani 1 1 d . . . . .
H20A H 0.790876 0.398625 0.939316 0.059 Uiso 1 1 calc R U . . .
H20B H 0.773549 0.294458 0.967907 0.059 Uiso 1 1 calc R U . . .
H20C H 0.629959 0.350006 0.921236 0.059 Uiso 1 1 calc R U . . .
C21 C 0.96581(14) 0.47019(10) 0.75037(9) 0.0270(3) Uani 1 1 d . . . . .
H21A H 1.014303 0.488767 0.696927 0.032 Uiso 1 1 calc R U . . .
H21B H 1.018947 0.415504 0.777360 0.032 Uiso 1 1 calc R U . . .
C22 C 0.98280(16) 0.54678(10) 0.82064(10) 0.0335(3) Uani 1 1 d . . . . .
H22A H 0.938762 0.602775 0.792577 0.050 Uiso 1 1 calc R U . . .
H22B H 1.089769 0.556689 0.842066 0.050 Uiso 1 1 calc R U . . .
H22C H 0.930776 0.530095 0.872462 0.050 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 1.2364(17) . ?
O2 C14 1.2456(16) . ?
N1 C5 1.3635(17) . ?
N1 C2 1.3803(17) . ?
N1 H1 0.8800 . ?
N2 C6 1.3694(17) . ?
N2 C9 1.3744(17) . ?
N2 H2 0.8800 . ?
N3 C10 1.3581(17) . ?
N3 C13 1.3805(17) . ?
N3 H3 0.8800 . ?
C1 C2 1.4188(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.4003(18) . ?
C3 C4 1.4056(19) . ?
C3 C15 1.5039(18) . ?
C4 C5 1.4050(18) . ?
C4 C17 1.5042(18) . ?
C5 C6 1.4444(18) . ?
C6 C7 1.3834(19) . ?
C7 C8 1.401(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3820(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.4465(18) . ?
C10 C11 1.4078(18) . ?
C11 C12 1.4039(19) . ?
C11 C19 1.5072(18) . ?
C12 C13 1.4031(18) . ?
C12 C21 1.5047(17) . ?
C13 C14 1.4080(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.524(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.529(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.529(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.5246(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C5 N1 C2 109.37(11) . . ?
C5 N1 H1 125.3 . . ?
C2 N1 H1 125.3 . . ?
C6 N2 C9 110.26(11) . . ?
C6 N2 H2 124.9 . . ?
C9 N2 H2 124.9 . . ?
C10 N3 C13 109.76(11) . . ?
C10 N3 H3 125.1 . . ?
C13 N3 H3 125.1 . . ?
O1 C1 C2 125.45(13) . . ?
O1 C1 H1A 117.3 . . ?
C2 C1 H1A 117.3 . . ?
N1 C2 C3 107.63(11) . . ?
N1 C2 C1 122.38(12) . . ?
C3 C2 C1 129.92(12) . . ?
C2 C3 C4 107.71(11) . . ?
C2 C3 C15 125.86(12) . . ?
C4 C3 C15 126.40(12) . . ?
C5 C4 C3 106.85(11) . . ?
C5 C4 C17 126.08(12) . . ?
C3 C4 C17 127.05(12) . . ?
N1 C5 C4 108.43(11) . . ?
N1 C5 C6 121.36(11) . . ?
C4 C5 C6 130.20(12) . . ?
N2 C6 C7 106.94(12) . . ?
N2 C6 C5 121.09(11) . . ?
C7 C6 C5 131.86(12) . . ?
C6 C7 C8 108.00(12) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 H7 126.0 . . ?
C9 C8 C7 107.79(12) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
N2 C9 C8 107.00(11) . . ?
N2 C9 C10 120.53(11) . . ?
C8 C9 C10 132.31(12) . . ?
N3 C10 C11 108.10(11) . . ?
N3 C10 C9 120.87(11) . . ?
C11 C10 C9 131.00(12) . . ?
C12 C11 C10 107.20(11) . . ?
C12 C11 C19 126.84(12) . . ?
C10 C11 C19 125.95(12) . . ?
C13 C12 C11 107.41(11) . . ?
C13 C12 C21 125.22(12) . . ?
C11 C12 C21 127.37(12) . . ?
N3 C13 C12 107.53(11) . . ?
N3 C13 C14 121.14(12) . . ?
C12 C13 C14 131.32(12) . . ?
O2 C14 C13 124.37(13) . . ?
O2 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C3 C15 C16 112.23(12) . . ?
C3 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C3 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 C18 113.44(12) . . ?
C4 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C4 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 C20 113.99(12) . . ?
C11 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C11 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 C22 112.90(11) . . ?
C12 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C12 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_WF-4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2298883'
loop_
_audit_author_name
_audit_author_address
'Qing He'
;Hunan University
China
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H39 N3 O3'
_chemical_formula_weight         537.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1718(7)
_cell_length_b                   11.1929(7)
_cell_length_c                   12.4287(8)
_cell_angle_alpha                86.208(3)
_cell_angle_beta                 68.959(3)
_cell_angle_gamma                88.712(3)
_cell_volume                     1447.34(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    8017
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      53.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.397
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23837
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.321
_diffrn_reflns_theta_max         52.996
_diffrn_reflns_theta_full        52.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5103
_reflns_number_gt                3849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5103
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1515
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6718(6) 0.0219(4) 0.5216(5) 0.127(2) Uani 1 1 d . . . . .
H1A H 0.690489 0.009388 0.592712 0.191 Uiso 1 1 calc R U . . .
H1B H 0.676195 -0.054903 0.486699 0.191 Uiso 1 1 calc R U . . .
H1C H 0.585559 0.055619 0.539594 0.191 Uiso 1 1 calc R U . . .
C2 C 0.7681(4) 0.1066(3) 0.4386(3) 0.0604(9) Uani 1 1 d . . . . .
H2A H 0.855346 0.074965 0.425392 0.073 Uiso 1 1 calc R U . . .
H2B H 0.755173 0.111241 0.363683 0.073 Uiso 1 1 calc R U . . .
C3 C 0.7585(3) 0.2305(3) 0.4813(3) 0.0460(7) Uani 1 1 d . . . . .
C4 C 0.6768(3) 0.3192(3) 0.4665(3) 0.0492(8) Uani 1 1 d . . . . .
C5 C 0.5914(4) 0.3199(4) 0.4060(4) 0.0783(13) Uani 1 1 d . . . . .
H5 H 0.587486 0.249333 0.368901 0.094 Uiso 1 1 calc R U . . .
C6 C 0.8223(3) 0.2752(3) 0.5493(3) 0.050 Uani 1 1 d . . . . .
C7 C 0.9059(4) 0.2002(3) 0.6010(4) 0.079 Uani 1 1 d . . . . .
H7A H 0.909154 0.238275 0.669571 0.095 Uiso 1 1 calc R U . . .
H7B H 0.867181 0.119779 0.626703 0.095 Uiso 1 1 calc R U . . .
C8 C 1.0329(4) 0.1881(4) 0.5202(4) 0.0923(14) Uani 1 1 d . . . . .
H8A H 1.030359 0.147083 0.453737 0.138 Uiso 1 1 calc R U . . .
H8B H 1.084401 0.141255 0.557042 0.138 Uiso 1 1 calc R U . . .
H8C H 1.071291 0.267598 0.494035 0.138 Uiso 1 1 calc R U . . .
C9 C 0.7794(3) 0.3923(2) 0.5738(3) 0.0386(6) Uani 1 1 d . . . . .
C10 C 0.8120(3) 0.4830(2) 0.6388(2) 0.0375(6) Uani 1 1 d . . . . .
C11 C 0.9325(3) 0.4836(3) 0.6524(3) 0.0412(7) Uani 1 1 d . . . . .
H11 H 0.991851 0.421644 0.620992 0.049 Uiso 1 1 calc R U . . .
C12 C 0.9672(3) 0.5706(3) 0.7092(3) 0.0425(7) Uani 1 1 d . . . . .
H12 H 1.048266 0.568189 0.717939 0.051 Uiso 1 1 calc R U . . .
C13 C 0.8807(3) 0.6614(2) 0.7533(3) 0.0378(6) Uani 1 1 d . . . . .
C14 C 0.7604(2) 0.6654(2) 0.7386(2) 0.0360(6) Uani 1 1 d . . . . .
C15 C 0.7264(3) 0.5753(2) 0.6833(2) 0.0378(6) Uani 1 1 d . . . . .
H15 H 0.644660 0.576622 0.675857 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6995(2) 0.7758(2) 0.7841(2) 0.0353(6) Uani 1 1 d . . . . .
C17 C 0.5870(2) 0.8328(2) 0.7873(2) 0.0371(6) Uani 1 1 d . . . . .
H17 H 0.529714 0.795108 0.759204 0.044 Uiso 1 1 calc R U . . .
C18 C 0.5579(2) 0.9450(2) 0.8317(2) 0.0376(6) Uani 1 1 d . . . . .
C19 C 0.6435(3) 0.9978(3) 0.8761(3) 0.0402(7) Uani 1 1 d . . . . .
H19 H 0.622843 1.073631 0.908215 0.048 Uiso 1 1 calc R U . . .
C20 C 0.7555(3) 0.9424(3) 0.8739(3) 0.0402(7) Uani 1 1 d . . . . .
H20 H 0.811551 0.978769 0.904390 0.048 Uiso 1 1 calc R U . . .
C21 C 0.7842(2) 0.8324(2) 0.8263(2) 0.0369(6) Uani 1 1 d . . . . .
C22 C 0.4421(3) 1.0080(3) 0.8303(3) 0.0387(7) Uani 1 1 d . . . . .
C23 C 0.4185(3) 1.1293(3) 0.8097(3) 0.0418(7) Uani 1 1 d . . . . .
C24 C 0.5119(3) 1.2315(3) 0.7851(3) 0.0506(8) Uani 1 1 d . . . . .
H24A H 0.503433 1.285190 0.721712 0.061 Uiso 1 1 calc R U . . .
H24B H 0.600266 1.199202 0.758638 0.061 Uiso 1 1 calc R U . . .
C25 C 0.4911(3) 1.3043(3) 0.8903(4) 0.0645(10) Uani 1 1 d . . . . .
H25A H 0.402681 1.333783 0.919027 0.097 Uiso 1 1 calc R U . . .
H25B H 0.550546 1.372362 0.868054 0.097 Uiso 1 1 calc R U . . .
H25C H 0.506872 1.253422 0.951074 0.097 Uiso 1 1 calc R U . . .
C26 C 0.2908(3) 1.1386(3) 0.8151(3) 0.0450(7) Uani 1 1 d . . . . .
C27 C 0.2231(3) 1.2507(3) 0.7958(4) 0.0639(10) Uani 1 1 d . . . . .
H27A H 0.129460 1.236320 0.830055 0.077 Uiso 1 1 calc R U . . .
H27B H 0.243407 1.314984 0.837526 0.077 Uiso 1 1 calc R U . . .
C28 C 0.2566(5) 1.2943(5) 0.6710(5) 0.1112(19) Uani 1 1 d . . . . .
H28A H 0.348303 1.313396 0.637047 0.167 Uiso 1 1 calc R U . . .
H28B H 0.206566 1.366143 0.666304 0.167 Uiso 1 1 calc R U . . .
H28C H 0.236814 1.231557 0.628489 0.167 Uiso 1 1 calc R U . . .
C29 C 0.2388(3) 1.0232(3) 0.8381(3) 0.0431(7) Uani 1 1 d . . . . .
C30 C 0.1141(3) 0.9822(3) 0.8543(3) 0.0507(8) Uani 1 1 d . . . . .
H30 H 0.052757 1.040452 0.849708 0.061 Uiso 1 1 calc R U . . .
C31 C 0.3261(4) 0.5996(4) 0.9238(5) 0.0979(16) Uani 1 1 d . . . . .
H31A H 0.377467 0.556555 0.964394 0.118 Uiso 1 1 calc R U . . .
H31B H 0.374775 0.600927 0.839603 0.118 Uiso 1 1 calc R U . . .
C32 C 0.2002(5) 0.5394(5) 0.9524(6) 0.121(2) Uani 1 1 d . . . . .
H32A H 0.183630 0.525841 0.881094 0.146 Uiso 1 1 calc R U . . .
H32B H 0.198908 0.461116 0.994906 0.146 Uiso 1 1 calc R U . . .
C33 C 0.1028(4) 0.6201(3) 1.0250(4) 0.0752(11) Uani 1 1 d . . . . .
H33A H 0.044749 0.576650 1.095785 0.090 Uiso 1 1 calc R U . . .
H33B H 0.051330 0.658620 0.982034 0.090 Uiso 1 1 calc R U . . .
C34 C 0.1821(4) 0.7100(4) 1.0531(3) 0.0705(11) Uani 1 1 d . . . . .
H34A H 0.139762 0.789306 1.061689 0.085 Uiso 1 1 calc R U . . .
H34B H 0.195203 0.684786 1.125972 0.085 Uiso 1 1 calc R U . . .
N1 N 0.6912(2) 0.4163(2) 0.5236(2) 0.0458(6) Uani 1 1 d . . . . .
H1 H 0.649134 0.484234 0.526954 0.055 Uiso 1 1 calc R U . . .
N2 N 0.8918(2) 0.7612(2) 0.8088(2) 0.0417(6) Uani 1 1 d . . . . .
H2 H 0.956857 0.776966 0.829769 0.050 Uiso 1 1 calc R U . . .
N3 N 0.3334(2) 0.9451(2) 0.8462(2) 0.0394(6) Uani 1 1 d . . . . .
H3 H 0.324705 0.866976 0.859616 0.047 Uiso 1 1 calc R U . . .
O1 O 0.5216(3) 0.4032(3) 0.3969(3) 0.1064(12) Uani 1 1 d . . . . .
O2 O 0.0789(2) 0.8766(2) 0.8741(2) 0.0599(6) Uani 1 1 d . . . . .
O3 O 0.3009(2) 0.7152(2) 0.9591(2) 0.0663(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.497(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.506(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.381(4) . ?
C3 C6 1.406(4) . ?
C4 N1 1.380(4) . ?
C4 C5 1.411(4) . ?
C5 O1 1.228(4) . ?
C5 H5 0.9500 . ?
C6 C9 1.400(4) . ?
C6 C7 1.521(5) . ?
C7 C8 1.423(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.356(3) . ?
C9 C10 1.468(4) . ?
C10 C15 1.392(4) . ?
C10 C11 1.416(4) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 N2 1.382(3) . ?
C13 C14 1.419(4) . ?
C14 C15 1.390(4) . ?
C14 C16 1.446(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 C21 1.413(4) . ?
C17 C18 1.390(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.419(4) . ?
C18 C22 1.465(4) . ?
C19 C20 1.376(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 N2 1.387(3) . ?
C22 N3 1.362(3) . ?
C22 C23 1.402(4) . ?
C23 C26 1.406(4) . ?
C23 C24 1.506(4) . ?
C24 C25 1.530(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C29 1.397(4) . ?
C26 C27 1.501(4) . ?
C27 C28 1.508(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 N3 1.384(3) . ?
C29 C30 1.417(4) . ?
C30 O2 1.235(4) . ?
C30 H30 0.9500 . ?
C31 O3 1.384(4) . ?
C31 C32 1.487(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.474(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.493(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O3 1.418(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
N3 H3 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 112.6(3) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C6 107.3(3) . . ?
C4 C3 C2 125.1(3) . . ?
C6 C3 C2 127.4(3) . . ?
N1 C4 C3 107.5(3) . . ?
N1 C4 C5 122.4(3) . . ?
C3 C4 C5 130.1(3) . . ?
O1 C5 C4 126.0(3) . . ?
O1 C5 H5 117.0 . . ?
C4 C5 H5 117.0 . . ?
C3 C6 C9 107.8(3) . . ?
C3 C6 C7 124.4(3) . . ?
C9 C6 C7 127.1(3) . . ?
C8 C7 C6 111.8(4) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C6 107.0(2) . . ?
N1 C9 C10 120.3(2) . . ?
C6 C9 C10 132.7(3) . . ?
C15 C10 C11 118.3(3) . . ?
C15 C10 C9 120.0(2) . . ?
C11 C10 C9 121.6(2) . . ?
C12 C11 C10 122.6(3) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
N2 C13 C12 130.6(2) . . ?
N2 C13 C14 108.7(2) . . ?
C12 C13 C14 120.6(3) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 C16 133.2(2) . . ?
C13 C14 C16 106.6(2) . . ?
C14 C15 C10 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C17 C16 C21 119.6(2) . . ?
C17 C16 C14 133.7(2) . . ?
C21 C16 C14 106.6(2) . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 118.8(2) . . ?
C17 C18 C22 120.2(2) . . ?
C19 C18 C22 121.0(2) . . ?
C20 C19 C18 121.9(3) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 118.2(2) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
N2 C21 C20 129.7(2) . . ?
N2 C21 C16 108.9(2) . . ?
C20 C21 C16 121.4(2) . . ?
N3 C22 C23 108.2(2) . . ?
N3 C22 C18 120.0(2) . . ?
C23 C22 C18 131.7(3) . . ?
C22 C23 C26 107.2(3) . . ?
C22 C23 C24 126.9(3) . . ?
C26 C23 C24 125.8(3) . . ?
C23 C24 C25 113.0(3) . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C29 C26 C23 107.5(3) . . ?
C29 C26 C27 125.9(3) . . ?
C23 C26 C27 126.7(3) . . ?
C28 C27 C26 115.0(3) . . ?
C28 C27 H27A 108.5 . . ?
C26 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
C26 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C26 107.7(2) . . ?
N3 C29 C30 121.4(3) . . ?
C26 C29 C30 130.9(3) . . ?
O2 C30 C29 125.2(3) . . ?
O2 C30 H30 117.4 . . ?
C29 C30 H30 117.4 . . ?
O3 C31 C32 107.0(4) . . ?
O3 C31 H31A 110.3 . . ?
C32 C31 H31A 110.3 . . ?
O3 C31 H31B 110.3 . . ?
C32 C31 H31B 110.3 . . ?
H31A C31 H31B 108.6 . . ?
C33 C32 C31 106.3(4) . . ?
C33 C32 H32A 110.5 . . ?
C31 C32 H32A 110.5 . . ?
C33 C32 H32B 110.5 . . ?
C31 C32 H32B 110.5 . . ?
H32A C32 H32B 108.7 . . ?
C32 C33 C34 102.7(3) . . ?
C32 C33 H33A 111.2 . . ?
C34 C33 H33A 111.2 . . ?
C32 C33 H33B 111.2 . . ?
C34 C33 H33B 111.2 . . ?
H33A C33 H33B 109.1 . . ?
O3 C34 C33 105.7(3) . . ?
O3 C34 H34A 110.6 . . ?
C33 C34 H34A 110.6 . . ?
O3 C34 H34B 110.6 . . ?
C33 C34 H34B 110.6 . . ?
H34A C34 H34B 108.7 . . ?
C9 N1 C4 110.3(2) . . ?
C9 N1 H1 124.8 . . ?
C4 N1 H1 124.8 . . ?
C13 N2 C21 109.1(2) . . ?
C13 N2 H2 125.4 . . ?
C21 N2 H2 125.4 . . ?
C22 N3 C29 109.4(2) . . ?
C22 N3 H3 125.3 . . ?
C29 N3 H3 125.3 . . ?
C31 O3 C34 106.1(3) . . ?

_refine_diff_density_max         1.120
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_cu_20211202_wf_3_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2298880'
loop_
_audit_author_name
_audit_author_address
'Qing He'
;Hunan University
China
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2022-02-10
_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        WF-3
_chemical_formula_moiety         '2(H2 O), 2(C22 H26 N4 O2)'
_chemical_formula_sum            'C44 H56 N8 O6'
_chemical_formula_weight         792.96
_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                   8.6855(7)
_cell_length_b                   9.1540(9)
_cell_length_c                   13.8725(13)
_cell_angle_alpha                105.506(6)
_cell_angle_beta                 102.442(6)
_cell_angle_gamma                90.015(6)
_cell_volume                     1035.89(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4144
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      72.155
_cell_measurement_theta_min      5.018
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_preparation       CHCl3/n-hexane
_exptl_crystal_recrystallization_method CHCl3/n-hexane
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5671
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.292
_diffrn_reflns_theta_min         5.023
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_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                3264
_reflns_number_total             3985
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         1.089
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.1186
_refine_ls_restrained_S_all      1.055
_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)+(0.1818P)²+1.4580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2934
_refine_ls_wR_factor_ref         0.3077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H3A-H4
 2.52 with sigma of 0.01
 H1-H3B
 2.52 with sigma of 0.01
 H4-H3B
 2.52 with sigma of 0.01
3.a Free rotating group:
 O3(H3A,H3B)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C16(H16A,H16B), C19(H19A,H19B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C1(H1A), C11(H11), C12(H12), C22(H22)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C5(H5A,H5B,H5C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.2567(3) 0.7039(3) 0.5014(2) 0.0399(7) Uani 1 1 d G . . . .
H3A H 0.329849 0.777498 0.524160 0.060 Uiso 1 1 d DG U . . .
H3B H 0.181401 0.737356 0.461955 0.060 Uiso 1 1 d DG U . . .
O1 O 0.0962(4) 0.8669(3) 0.6578(2) 0.0452(7) Uani 1 1 d . . . . .
N4 N 0.3816(3) 0.4437(3) 0.3717(2) 0.0279(6) Uani 1 1 d . . . . .
H4 H 0.341616 0.509812 0.417145 0.033 Uiso 1 1 calc DR U . . .
N1 N 0.1189(3) 0.5442(3) 0.6241(2) 0.0278(6) Uani 1 1 d . . . . .
H1 H 0.159031 0.573859 0.578876 0.033 Uiso 1 1 calc DR U . . .
O2 O 0.4111(4) 0.7408(3) 0.3416(2) 0.0456(7) Uani 1 1 d . . . . .
N2 N 0.2492(3) 0.3323(3) 0.4966(2) 0.0278(6) Uani 1 1 d . . . . .
N3 N 0.2487(4) 0.0284(4) 0.4951(2) 0.0427(8) Uani 1 1 d . . . . .
C15 C 0.4568(4) 0.2266(4) 0.2805(2) 0.0295(7) Uani 1 1 d . . . . .
C2 C 0.0522(4) 0.6366(4) 0.6973(2) 0.0285(7) Uani 1 1 d . . . . .
C9 C 0.1134(4) 0.3986(4) 0.6322(2) 0.0266(7) Uani 1 1 d . . . . .
C10 C 0.1810(4) 0.2839(4) 0.5606(2) 0.0280(7) Uani 1 1 d . . . . .
C14 C 0.3840(4) 0.2914(4) 0.3615(2) 0.0286(7) Uani 1 1 d . . . . .
C21 C 0.4511(4) 0.4772(4) 0.3003(2) 0.0289(7) Uani 1 1 d . . . . .
C3 C 0.0025(4) 0.5482(4) 0.7540(2) 0.0298(7) Uani 1 1 d . . . . .
C18 C 0.4979(4) 0.3439(4) 0.2418(2) 0.0289(7) Uani 1 1 d . . . . .
C1 C 0.0437(4) 0.7970(4) 0.7082(3) 0.0339(8) Uani 1 1 d . . . . .
H1A H -0.007316 0.853240 0.759168 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3157(4) 0.2321(4) 0.4315(2) 0.0281(7) Uani 1 1 d . . . . .
C4 C -0.0708(4) 0.6065(4) 0.8446(3) 0.0352(8) Uani 1 1 d . . . . .
H4A H -0.136996 0.523171 0.851194 0.042 Uiso 1 1 calc R U . . .
H4B H -0.140618 0.688250 0.832351 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4829(4) 0.0612(5) 0.2380(3) 0.0387(8) Uani 1 1 d . . . . .
H16A H 0.523465 0.017391 0.295853 0.046 Uiso 1 1 calc R U . . .
H16B H 0.564991 0.053447 0.197454 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0406(4) 0.3983(4) 0.7133(2) 0.0295(7) Uani 1 1 d . . . . .
C11 C 0.1780(5) 0.1291(4) 0.5589(3) 0.0354(8) Uani 1 1 d . . . . .
H11 H 0.125557 0.095632 0.603240 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3171(4) 0.0782(4) 0.4324(3) 0.0369(8) Uani 1 1 d . . . . .
H12 H 0.368277 0.008934 0.387107 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5749(4) 0.3319(5) 0.1529(3) 0.0368(8) Uani 1 1 d . . . . .
H19A H 0.640874 0.243115 0.146003 0.044 Uiso 1 1 calc R U . . .
H19B H 0.645311 0.423853 0.167356 0.044 Uiso 1 1 calc R U . . .
C7 C 0.0092(4) 0.2636(4) 0.7509(3) 0.0333(8) Uani 1 1 d . . . . .
H7A H -0.029535 0.174954 0.691092 0.040 Uiso 1 1 calc R U . . .
H7B H -0.074973 0.286330 0.789894 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1552(5) 0.2229(5) 0.8191(3) 0.0421(9) Uani 1 1 d . . . . .
H8A H 0.236772 0.194291 0.779660 0.063 Uiso 1 1 calc R U . . .
H8B H 0.127668 0.137518 0.843536 0.063 Uiso 1 1 calc R U . . .
H8C H 0.195138 0.310781 0.877912 0.063 Uiso 1 1 calc R U . . .
C22 C 0.4621(4) 0.6296(4) 0.2909(3) 0.0340(8) Uani 1 1 d . . . . .
H22 H 0.514246 0.644708 0.240416 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3341(6) -0.0329(5) 0.1700(3) 0.0511(10) Uani 1 1 d . . . . .
H17A H 0.293176 0.009435 0.112243 0.077 Uiso 1 1 calc R U . . .
H17B H 0.253880 -0.030052 0.210314 0.077 Uiso 1 1 calc R U . . .
H17C H 0.360023 -0.138187 0.143747 0.077 Uiso 1 1 calc R U . . .
C5 C 0.0520(5) 0.6678(6) 0.9446(3) 0.0526(11) Uani 1 1 d . . . . .
H5A H 0.113068 0.754898 0.940190 0.079 Uiso 1 1 calc R U . . .
H5B H 0.123129 0.588095 0.956175 0.079 Uiso 1 1 calc R U . . .
H5C H -0.001295 0.699841 1.001622 0.079 Uiso 1 1 calc R U . . .
C20 C 0.4554(5) 0.3150(7) 0.0516(3) 0.0536(12) Uani 1 1 d . . . . .
H20A H 0.511250 0.303071 -0.004013 0.080 Uiso 1 1 calc R U . . .
H20B H 0.394355 0.405675 0.056374 0.080 Uiso 1 1 calc R U . . .
H20C H 0.383705 0.225340 0.037584 0.080 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
O3 H3A 0.8699 . ?
O3 H3B 0.8696 . ?
O1 C1 1.217(5) . ?
N4 H4 0.8800 . ?
N4 C14 1.364(5) . ?
N4 C21 1.364(4) . ?
N1 H1 0.8800 . ?
N1 C2 1.370(4) . ?
N1 C9 1.368(4) . ?
O2 C22 1.216(5) . ?
N2 C10 1.332(4) . ?
N2 C13 1.331(4) . ?
N3 C11 1.345(5) . ?
N3 C12 1.322(5) . ?
C15 C14 1.401(5) . ?
C15 C18 1.400(5) . ?
C15 C16 1.508(5) . ?
C2 C3 1.395(5) . ?
C2 C1 1.439(5) . ?
C9 C10 1.458(4) . ?
C9 C6 1.406(4) . ?
C10 C11 1.411(5) . ?
C14 C13 1.456(5) . ?
C21 C18 1.388(5) . ?
C21 C22 1.441(5) . ?
C3 C4 1.502(4) . ?
C3 C6 1.406(5) . ?
C18 C19 1.504(4) . ?
C1 H1A 0.9500 . ?
C13 C12 1.412(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.524(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.530(6) . ?
C6 C7 1.508(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.526(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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
H3A O3 H3B 104.5 . . ?
C14 N4 H4 125.5 . . ?
C14 N4 C21 109.1(3) . . ?
C21 N4 H4 125.5 . . ?
C2 N1 H1 125.3 . . ?
C9 N1 H1 125.3 . . ?
C9 N1 C2 109.5(3) . . ?
C13 N2 C10 118.8(3) . . ?
C12 N3 C11 118.0(3) . . ?
C14 C15 C16 127.7(3) . . ?
C18 C15 C14 107.5(3) . . ?
C18 C15 C16 124.8(3) . . ?
N1 C2 C3 108.2(3) . . ?
N1 C2 C1 121.9(3) . . ?
C3 C2 C1 129.9(3) . . ?
N1 C9 C10 117.3(3) . . ?
N1 C9 C6 107.8(3) . . ?
C6 C9 C10 134.9(3) . . ?
N2 C10 C9 116.7(3) . . ?
N2 C10 C11 120.6(3) . . ?
C11 C10 C9 122.7(3) . . ?
N4 C14 C15 107.8(3) . . ?
N4 C14 C13 117.7(3) . . ?
C15 C14 C13 134.5(3) . . ?
N4 C21 C18 108.8(3) . . ?
N4 C21 C22 121.7(3) . . ?
C18 C21 C22 129.4(3) . . ?
C2 C3 C4 125.5(3) . . ?
C2 C3 C6 107.3(3) . . ?
C6 C3 C4 127.2(3) . . ?
C15 C18 C19 127.9(3) . . ?
C21 C18 C15 106.8(3) . . ?
C21 C18 C19 125.3(3) . . ?
O1 C1 C2 125.8(3) . . ?
O1 C1 H1A 117.1 . . ?
C2 C1 H1A 117.1 . . ?
N2 C13 C14 116.1(3) . . ?
N2 C13 C12 120.4(3) . . ?
C12 C13 C14 123.5(3) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.5(3) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 C17 113.8(3) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C9 C6 C3 107.2(3) . . ?
C9 C6 C7 126.9(3) . . ?
C3 C6 C7 125.9(3) . . ?
N3 C11 C10 120.7(3) . . ?
N3 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N3 C12 C13 121.4(3) . . ?
N3 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C18 C19 C20 112.8(3) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.7(3) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C22 C21 126.1(3) . . ?
O2 C22 H22 116.9 . . ?
C21 C22 H22 116.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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
N4 C14 C13 N2 3.3(4) . . . . ?
N4 C14 C13 C12 -176.9(3) . . . . ?
N4 C21 C18 C15 -0.8(3) . . . . ?
N4 C21 C18 C19 178.1(3) . . . . ?
N4 C21 C22 O2 -1.4(5) . . . . ?
N1 C2 C3 C4 177.4(3) . . . . ?
N1 C2 C3 C6 -0.1(3) . . . . ?
N1 C2 C1 O1 -2.0(5) . . . . ?
N1 C9 C10 N2 3.1(4) . . . . ?
N1 C9 C10 C11 -177.9(3) . . . . ?
N1 C9 C6 C3 -0.1(3) . . . . ?
N1 C9 C6 C7 -179.7(3) . . . . ?
N2 C10 C11 N3 2.3(5) . . . . ?
N2 C13 C12 N3 2.2(5) . . . . ?
C15 C14 C13 N2 -176.7(3) . . . . ?
C15 C14 C13 C12 3.1(6) . . . . ?
C15 C18 C19 C20 92.9(5) . . . . ?
C2 N1 C9 C10 -179.4(3) . . . . ?
C2 N1 C9 C6 0.0(3) . . . . ?
C2 C3 C4 C5 -84.0(4) . . . . ?
C2 C3 C6 C9 0.1(3) . . . . ?
C2 C3 C6 C7 179.8(3) . . . . ?
C9 N1 C2 C3 0.0(3) . . . . ?
C9 N1 C2 C1 179.0(3) . . . . ?
C9 C10 C11 N3 -176.7(3) . . . . ?
C9 C6 C7 C8 79.1(4) . . . . ?
C10 N2 C13 C14 178.2(3) . . . . ?
C10 N2 C13 C12 -1.6(5) . . . . ?
C10 C9 C6 C3 179.2(3) . . . . ?
C10 C9 C6 C7 -0.5(6) . . . . ?
C14 N4 C21 C18 0.7(3) . . . . ?
C14 N4 C21 C22 178.4(3) . . . . ?
C14 C15 C18 C21 0.6(3) . . . . ?
C14 C15 C18 C19 -178.2(3) . . . . ?
C14 C15 C16 C17 76.3(5) . . . . ?
C14 C13 C12 N3 -177.6(3) . . . . ?
C21 N4 C14 C15 -0.3(3) . . . . ?
C21 N4 C14 C13 179.7(3) . . . . ?
C21 C18 C19 C20 -85.7(5) . . . . ?
C3 C2 C1 O1 176.7(4) . . . . ?
C3 C6 C7 C8 -100.5(4) . . . . ?
C18 C15 C14 N4 -0.2(3) . . . . ?
C18 C15 C14 C13 179.8(3) . . . . ?
C18 C15 C16 C17 -101.3(4) . . . . ?
C18 C21 C22 O2 175.9(4) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C1 C2 C3 C6 -178.9(3) . . . . ?
C13 N2 C10 C9 178.5(3) . . . . ?
C13 N2 C10 C11 -0.5(5) . . . . ?
C4 C3 C6 C9 -177.3(3) . . . . ?
C4 C3 C6 C7 2.4(5) . . . . ?
C16 C15 C14 N4 -178.1(3) . . . . ?
C16 C15 C14 C13 1.9(6) . . . . ?
C16 C15 C18 C21 178.6(3) . . . . ?
C16 C15 C18 C19 -0.2(5) . . . . ?
C6 C9 C10 N2 -176.1(3) . . . . ?
C6 C9 C10 C11 2.9(6) . . . . ?
C6 C3 C4 C5 92.9(4) . . . . ?
C11 N3 C12 C13 -0.4(6) . . . . ?
C12 N3 C11 C10 -1.7(6) . . . . ?
C22 C21 C18 C15 -178.3(3) . . . . ?
C22 C21 C18 C19 0.6(5) . . . . ?


_olex2_submission_original_sample_id WF-3
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_20211202_wf_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2298881'
loop_
_audit_author_name
_audit_author_address
'Qing He'
;Hunan University
China
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2022-02-09
_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        WF-2
_chemical_formula_moiety         'C22 H26 N4 O2'
_chemical_formula_sum            'C22 H26 N4 O2'
_chemical_formula_weight         378.47
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.852(15)
_cell_length_b                   8.3792(16)
_cell_length_c                   16.947(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.99(3)
_cell_angle_gamma                90
_cell_volume                     4054(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    174
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      43.12
_cell_measurement_theta_min      6.34
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.4280
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_preparation       'THF ANN nhexane'
_exptl_crystal_recrystallization_method 'nhexane to THF'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1291
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11024
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        63.870
_diffrn_reflns_theta_max         63.870
_diffrn_reflns_theta_min         3.096
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_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                1537
_reflns_number_total             3265
_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 V8.40C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40C (?, 2016)'
_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         0.561
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.0028(7)
_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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2199
_refine_ls_R_factor_gt           0.1445
_refine_ls_restrained_S_all      1.069
_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)+(0.2800P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3864
_refine_ls_wR_factor_ref         0.4465
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C3
 1.51 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C19(H19A,H19B), C16(H16A,H16B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C12(H12), C1(H1A), C22(H22), C11(H11)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C8(H8A,H8B,H8C)
;
_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
O2 O 0.4836(2) 1.1440(6) 0.4270(4) 0.0609(17) Uani 1 1 d . . . . .
O1 O 0.4757(2) 0.3704(6) 0.5634(3) 0.0603(17) Uani 1 1 d . . . . .
N4 N 0.5769(3) 1.0251(7) 0.4821(4) 0.0489(18) Uani 1 1 d . . . . .
H4 H 0.558121 0.958051 0.496834 0.059 Uiso 1 1 calc R U . . .
N1 N 0.5718(3) 0.4609(7) 0.5889(4) 0.0495(18) Uani 1 1 d . . . . .
H1 H 0.553509 0.534839 0.559196 0.059 Uiso 1 1 calc R U . . .
N2 N 0.6863(3) 0.5559(8) 0.5757(5) 0.062(2) Uani 1 1 d . . . . .
N3 N 0.6882(3) 0.8179(7) 0.5185(5) 0.062(2) Uani 1 1 d . . . . .
C9 C 0.6192(3) 0.4619(8) 0.6119(5) 0.050(2) Uani 1 1 d . . . . .
C18 C 0.6038(3) 1.2404(8) 0.4308(5) 0.047(2) Uani 1 1 d . . . . .
C15 C 0.6421(3) 1.1356(9) 0.4644(5) 0.053(2) Uani 1 1 d . . . . .
C21 C 0.5636(3) 1.1691(9) 0.4426(5) 0.052(2) Uani 1 1 d . . . . .
C2 C 0.5569(3) 0.3266(8) 0.6194(5) 0.048(2) Uani 1 1 d . . . . .
C6 C 0.6357(3) 0.3258(8) 0.6606(5) 0.054(2) Uani 1 1 d . . . . .
C12 C 0.6229(3) 0.7403(8) 0.5619(5) 0.052(2) Uani 1 1 d . . . . .
H12 H 0.593597 0.764493 0.570441 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6235(3) 1.0031(8) 0.4945(5) 0.051(2) Uani 1 1 d . . . . .
C4 C 0.5951(3) 0.0934(8) 0.7144(5) 0.057(2) Uani 1 1 d D . . . .
H4A H 0.625411 0.036448 0.725879 0.068 Uiso 1 1 calc R U . . .
H4B H 0.570320 0.021849 0.681281 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6459(3) 0.8508(9) 0.5280(5) 0.053(2) Uani 1 1 d . . . . .
C10 C 0.6443(3) 0.5891(9) 0.5839(5) 0.056(2) Uani 1 1 d . . . . .
C3 C 0.5969(3) 0.2412(9) 0.6660(5) 0.056(2) Uani 1 1 d D . . . .
C19 C 0.6050(4) 1.3932(8) 0.3854(5) 0.059(2) Uani 1 1 d . . . . .
H19A H 0.637800 1.430993 0.398744 0.070 Uiso 1 1 calc R U . . .
H19B H 0.586695 1.475274 0.404484 0.070 Uiso 1 1 calc R U . . .
C1 C 0.5085(4) 0.2874(9) 0.6052(5) 0.056(2) Uani 1 1 d . . . . .
H1A H 0.501026 0.192263 0.629174 0.067 Uiso 1 1 calc R U . . .
C22 C 0.5165(3) 1.2206(9) 0.4172(5) 0.053(2) Uani 1 1 d . . . . .
H22 H 0.509848 1.321388 0.390687 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5852(4) 0.1319(11) 0.7961(6) 0.073(3) Uani 1 1 d . . . . .
H5A H 0.555964 0.192462 0.785077 0.109 Uiso 1 1 calc R U . . .
H5B H 0.611043 0.195538 0.830915 0.109 Uiso 1 1 calc R U . . .
H5C H 0.582360 0.032332 0.824577 0.109 Uiso 1 1 calc R U . . .
C16 C 0.6916(3) 1.1647(9) 0.4628(6) 0.062(2) Uani 1 1 d . . . . .
H16A H 0.713359 1.104340 0.508368 0.075 Uiso 1 1 calc R U . . .
H16B H 0.698988 1.279600 0.472406 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7065(4) 0.6738(9) 0.5447(6) 0.068(3) Uani 1 1 d . . . . .
H11 H 0.737068 0.653290 0.540887 0.081 Uiso 1 1 calc R U . . .
C7 C 0.6859(3) 0.2828(10) 0.7001(6) 0.068(3) Uani 1 1 d . . . . .
H7A H 0.703213 0.291678 0.658606 0.082 Uiso 1 1 calc R U . . .
H7B H 0.687737 0.170387 0.718732 0.082 Uiso 1 1 calc R U . . .
C20 C 0.5847(4) 1.3734(10) 0.2896(6) 0.076(3) Uani 1 1 d . . . . .
H20A H 0.590118 1.471567 0.262261 0.114 Uiso 1 1 calc R U . . .
H20B H 0.550953 1.352552 0.275290 0.114 Uiso 1 1 calc R U . . .
H20C H 0.600252 1.283878 0.271218 0.114 Uiso 1 1 calc R U . . .
C17 C 0.6998(4) 1.1152(11) 0.3810(6) 0.072(3) Uani 1 1 d . . . . .
H17A H 0.678900 1.176242 0.335738 0.108 Uiso 1 1 calc R U . . .
H17B H 0.693321 1.000968 0.371742 0.108 Uiso 1 1 calc R U . . .
H17C H 0.732437 1.136669 0.383304 0.108 Uiso 1 1 calc R U . . .
C8 C 0.7093(5) 0.3886(14) 0.7733(9) 0.112(5) Uani 1 1 d . . . . .
H8A H 0.703669 0.500882 0.757287 0.168 Uiso 1 1 calc R U . . .
H8B H 0.743073 0.367818 0.791072 0.168 Uiso 1 1 calc R U . . .
H8C H 0.696234 0.365393 0.818828 0.168 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
O2 C22 1.223(10) . ?
O1 C1 1.241(10) . ?
N4 H4 0.8800 . ?
N4 C21 1.381(9) . ?
N4 C14 1.356(11) . ?
N1 H1 0.8800 . ?
N1 C9 1.354(11) . ?
N1 C2 1.366(9) . ?
N2 C10 1.332(11) . ?
N2 C11 1.340(11) . ?
N3 C13 1.349(11) . ?
N3 C11 1.346(10) . ?
C9 C6 1.410(10) . ?
C9 C10 1.459(11) . ?
C18 C15 1.422(11) . ?
C18 C21 1.405(12) . ?
C18 C19 1.499(11) . ?
C15 C14 1.403(11) . ?
C15 C16 1.508(12) . ?
C21 C22 1.414(12) . ?
C2 C3 1.417(12) . ?
C2 C1 1.433(12) . ?
C6 C3 1.384(12) . ?
C6 C7 1.496(13) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(12) . ?
C12 C10 1.419(10) . ?
C14 C13 1.475(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.496(10) . ?
C4 C5 1.532(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.568(13) . ?
C1 H1A 0.9500 . ?
C22 H22 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.533(13) . ?
C11 H11 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.518(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C21 N4 H4 125.4 . . ?
C14 N4 H4 125.4 . . ?
C14 N4 C21 109.3(7) . . ?
C9 N1 H1 125.5 . . ?
C9 N1 C2 108.9(7) . . ?
C2 N1 H1 125.5 . . ?
C10 N2 C11 115.6(7) . . ?
C11 N3 C13 116.6(7) . . ?
N1 C9 C6 108.7(7) . . ?
N1 C9 C10 120.3(7) . . ?
C6 C9 C10 131.0(9) . . ?
C15 C18 C19 126.5(8) . . ?
C21 C18 C15 107.4(7) . . ?
C21 C18 C19 125.9(8) . . ?
C18 C15 C16 124.8(7) . . ?
C14 C15 C18 106.1(8) . . ?
C14 C15 C16 129.0(8) . . ?
N4 C21 C18 107.7(7) . . ?
N4 C21 C22 122.3(8) . . ?
C18 C21 C22 129.9(7) . . ?
N1 C2 C3 108.2(8) . . ?
N1 C2 C1 123.3(7) . . ?
C3 C2 C1 128.5(7) . . ?
C9 C6 C7 126.1(8) . . ?
C3 C6 C9 107.2(8) . . ?
C3 C6 C7 126.6(7) . . ?
C13 C12 H12 120.9 . . ?
C13 C12 C10 118.1(8) . . ?
C10 C12 H12 120.9 . . ?
N4 C14 C15 109.4(7) . . ?
N4 C14 C13 120.4(7) . . ?
C15 C14 C13 129.9(9) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.6(7) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
N3 C13 C12 120.8(7) . . ?
N3 C13 C14 117.8(7) . . ?
C12 C13 C14 121.3(8) . . ?
N2 C10 C9 118.1(7) . . ?
N2 C10 C12 121.6(8) . . ?
C12 C10 C9 120.2(9) . . ?
C2 C3 C4 124.4(8) . . ?
C6 C3 C2 106.9(7) . . ?
C6 C3 C4 128.6(8) . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C18 C19 C20 112.4(7) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
O1 C1 C2 123.8(7) . . ?
O1 C1 H1A 118.1 . . ?
C2 C1 H1A 118.1 . . ?
O2 C22 C21 124.4(7) . . ?
O2 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C15 C16 C17 112.9(8) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
N2 C11 N3 127.3(9) . . ?
N2 C11 H11 116.4 . . ?
N3 C11 H11 116.4 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C6 C7 C8 112.8(9) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
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 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
N4 C21 C22 O2 -0.4(12) . . . . ?
N4 C14 C13 N3 162.3(8) . . . . ?
N4 C14 C13 C12 -12.6(12) . . . . ?
N1 C9 C6 C3 0.5(9) . . . . ?
N1 C9 C6 C7 -178.6(8) . . . . ?
N1 C9 C10 N2 -151.4(8) . . . . ?
N1 C9 C10 C12 25.1(11) . . . . ?
N1 C2 C3 C6 -1.6(9) . . . . ?
N1 C2 C3 C4 175.3(7) . . . . ?
N1 C2 C1 O1 0.8(12) . . . . ?
C9 N1 C2 C3 1.9(8) . . . . ?
C9 N1 C2 C1 -179.0(7) . . . . ?
C9 C6 C3 C2 0.7(9) . . . . ?
C9 C6 C3 C4 -176.0(8) . . . . ?
C9 C6 C7 C8 72.5(12) . . . . ?
C18 C15 C14 N4 -1.1(9) . . . . ?
C18 C15 C14 C13 173.0(8) . . . . ?
C18 C15 C16 C17 -82.8(10) . . . . ?
C18 C21 C22 O2 175.7(8) . . . . ?
C15 C18 C21 N4 -0.1(9) . . . . ?
C15 C18 C21 C22 -176.7(8) . . . . ?
C15 C18 C19 C20 101.3(11) . . . . ?
C15 C14 C13 N3 -11.3(13) . . . . ?
C15 C14 C13 C12 173.8(8) . . . . ?
C21 N4 C14 C15 1.1(9) . . . . ?
C21 N4 C14 C13 -173.7(7) . . . . ?
C21 C18 C15 C14 0.7(9) . . . . ?
C21 C18 C15 C16 178.5(8) . . . . ?
C21 C18 C19 C20 -73.8(11) . . . . ?
C2 N1 C9 C6 -1.5(8) . . . . ?
C2 N1 C9 C10 176.9(7) . . . . ?
C6 C9 C10 N2 26.6(13) . . . . ?
C6 C9 C10 C12 -156.9(8) . . . . ?
C14 N4 C21 C18 -0.6(8) . . . . ?
C14 N4 C21 C22 176.3(7) . . . . ?
C14 C15 C16 C17 94.4(10) . . . . ?
C13 N3 C11 N2 3.5(15) . . . . ?
C13 C12 C10 N2 2.9(13) . . . . ?
C13 C12 C10 C9 -173.5(8) . . . . ?
C10 N2 C11 N3 -2.8(14) . . . . ?
C10 C9 C6 C3 -177.7(8) . . . . ?
C10 C9 C6 C7 3.3(14) . . . . ?
C10 C12 C13 N3 -2.2(12) . . . . ?
C10 C12 C13 C14 172.6(7) . . . . ?
C3 C2 C1 O1 179.8(8) . . . . ?
C3 C6 C7 C8 -106.3(11) . . . . ?
C19 C18 C15 C14 -175.1(7) . . . . ?
C19 C18 C15 C16 2.6(13) . . . . ?
C19 C18 C21 N4 175.8(7) . . . . ?
C19 C18 C21 C22 -0.8(13) . . . . ?
C1 C2 C3 C6 179.4(7) . . . . ?
C1 C2 C3 C4 -3.8(13) . . . . ?
C5 C4 C3 C2 -77.6(11) . . . . ?
C5 C4 C3 C6 98.5(11) . . . . ?
C16 C15 C14 N4 -178.7(8) . . . . ?
C16 C15 C14 C13 -4.6(15) . . . . ?
C11 N2 C10 C9 175.8(8) . . . . ?
C11 N2 C10 C12 -0.6(12) . . . . ?
C11 N3 C13 C12 -0.8(13) . . . . ?
C11 N3 C13 C14 -175.8(8) . . . . ?
C7 C6 C3 C2 179.7(8) . . . . ?
C7 C6 C3 C4 3.0(15) . . . . ?


_olex2_submission_original_sample_id WF-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_cu_20211221_wf5_0m
_database_code_depnum_ccdc_archive 'CCDC 2298882'
loop_
_audit_author_name
_audit_author_address
'Qing He'
;Hunan University
China
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2022-02-06
_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        WF-5
_chemical_formula_moiety         'C30 H31 N3 O2'
_chemical_formula_sum            'C30 H31 N3 O2'
_chemical_formula_weight         465.58
_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      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                   14.386(6)
_cell_length_b                   7.518(5)
_cell_length_c                   22.733(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.20(2)
_cell_angle_gamma                90
_cell_volume                     2412(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1542
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      66.261
_cell_measurement_theta_min      6.176
_shelx_estimated_absorpt_T_max   0.785
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_preparation       THF/n-hexane
_exptl_crystal_recrystallization_method 'THF in-n-hexane out'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15781
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.732
_diffrn_reflns_theta_max         66.732
_diffrn_reflns_theta_min         4.019
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3132
_reflns_number_total             4207
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.224
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0028(4)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.064
_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)+(0.0538P)²+0.0166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C27(H27A,H27B), C7(H7A,H7B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N005(H005), C15(H15), C1(H1A), C11(H11), C12(H12), C18(H18),
 C20(H20), C21(H21), C30(H30)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C8(H8A,H8B,H8C), C5(H5A,H5B,H5C), C25(H25A,H25B,H25C)
;
_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 0.46874(9) -0.20121(19) 0.45249(6) 0.0341(3) Uani 1 1 d . . . . .
O2 O 0.56357(10) 1.6175(2) 0.63185(7) 0.0423(4) Uani 1 1 d . . . . .
N1 N 0.60896(11) 0.0696(2) 0.43876(7) 0.0275(4) Uani 1 1 d . . . . .
H1 H 0.584578 0.098047 0.470129 0.033 Uiso 1 1 calc R U . . .
N2 N 0.71242(11) 1.3662(2) 0.62534(7) 0.0277(4) Uani 1 1 d . . . . .
H2 H 0.660868 1.335742 0.599697 0.033 Uiso 1 1 calc R U . . .
N005 N 0.66776(11) 0.7225(2) 0.53257(7) 0.0281(4) Uani 1 1 d . . . . .
H005 H 0.608886 0.724506 0.538087 0.034 Uiso 1 1 calc R U . . .
C2 C 0.58180(13) -0.0739(3) 0.40160(8) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.69709(13) 0.0752(3) 0.36772(8) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.63627(13) -0.0714(3) 0.35676(8) 0.0272(4) Uani 1 1 d . . . . .
C14 C 0.70741(13) 0.5910(3) 0.50303(8) 0.0267(4) Uani 1 1 d . . . . .
C13 C 0.80276(13) 0.6348(3) 0.50308(8) 0.0273(4) Uani 1 1 d . . . . .
C10 C 0.72098(13) 0.3218(3) 0.44968(8) 0.0268(4) Uani 1 1 d . . . . .
C29 C 0.71901(13) 1.5078(3) 0.66410(8) 0.0293(4) Uani 1 1 d . . . . .
C15 C 0.66517(13) 0.4378(3) 0.47578(8) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.600191 0.412957 0.474972 0.033 Uiso 1 1 calc R U . . .
C16 C 0.82053(13) 0.8028(3) 0.53412(8) 0.0284(4) Uani 1 1 d . . . . .
C19 C 0.80554(13) 1.1173(3) 0.59810(8) 0.0283(4) Uani 1 1 d . . . . .
C17 C 0.73567(13) 0.8507(3) 0.55211(8) 0.0268(4) Uani 1 1 d . . . . .
C1 C 0.51322(13) -0.2001(3) 0.41101(9) 0.0301(4) Uani 1 1 d . . . . .
H1A H 0.499919 -0.293757 0.382558 0.036 Uiso 1 1 calc R U . . .
C9 C 0.67882(13) 0.1598(3) 0.41961(8) 0.0268(4) Uani 1 1 d . . . . .
C11 C 0.81750(13) 0.3620(3) 0.45140(9) 0.0316(5) Uani 1 1 d . . . . .
H11 H 0.855672 0.280335 0.434735 0.038 Uiso 1 1 calc R U . . .
C23 C 0.86074(14) 1.3684(3) 0.67716(8) 0.0296(4) Uani 1 1 d . . . . .
C12 C 0.85722(13) 0.5180(3) 0.47690(9) 0.0324(5) Uani 1 1 d . . . . .
H12 H 0.921599 0.544987 0.476495 0.039 Uiso 1 1 calc R U . . .
C22 C 0.79691(13) 1.2799(3) 0.63223(8) 0.0274(4) Uani 1 1 d . . . . .
C26 C 0.81153(14) 1.5100(3) 0.69757(8) 0.0289(4) Uani 1 1 d . . . . .
C18 C 0.72792(13) 1.0037(3) 0.58484(8) 0.0287(4) Uani 1 1 d . . . . .
H18 H 0.670703 1.030543 0.597967 0.034 Uiso 1 1 calc R U . . .
C20 C 0.89001(14) 1.0726(3) 0.57899(9) 0.0319(5) Uani 1 1 d . . . . .
H20 H 0.942700 1.150875 0.587857 0.038 Uiso 1 1 calc R U . . .
C4 C 0.63147(14) -0.2041(3) 0.30671(8) 0.0308(5) Uani 1 1 d . . . . .
H4A H 0.665400 -0.155155 0.276377 0.037 Uiso 1 1 calc R U . . .
H4B H 0.564350 -0.221155 0.287112 0.037 Uiso 1 1 calc R U . . .
C21 C 0.89820(14) 0.9174(3) 0.54762(9) 0.0327(5) Uani 1 1 d . . . . .
H21 H 0.955977 0.889218 0.535413 0.039 Uiso 1 1 calc R U . . .
C30 C 0.64167(14) 1.6250(3) 0.66550(9) 0.0338(5) Uani 1 1 d . . . . .
H30 H 0.651135 1.716704 0.694818 0.041 Uiso 1 1 calc R U . . .
C27 C 0.85039(14) 1.6419(3) 0.74586(9) 0.0332(5) Uani 1 1 d . . . . .
H27A H 0.905426 1.588421 0.773042 0.040 Uiso 1 1 calc R U . . .
H27B H 0.801340 1.667789 0.769767 0.040 Uiso 1 1 calc R U . . .
C7 C 0.76621(14) 0.1327(3) 0.32965(9) 0.0324(5) Uani 1 1 d . . . . .
H7A H 0.782003 0.259699 0.337739 0.039 Uiso 1 1 calc R U . . .
H7B H 0.735605 0.121829 0.286868 0.039 Uiso 1 1 calc R U . . .
C24 C 0.96332(14) 1.3226(3) 0.69987(10) 0.0373(5) Uani 1 1 d . . . . .
H24A H 0.973033 1.194790 0.692507 0.045 Uiso 1 1 calc R U . . .
H24B H 0.978859 1.342535 0.743730 0.045 Uiso 1 1 calc R U . . .
C28 C 0.88105(16) 1.8153(3) 0.72075(10) 0.0389(5) Uani 1 1 d . . . . .
H28A H 0.922168 1.789121 0.692155 0.058 Uiso 1 1 calc R U . . .
H28B H 0.915763 1.887905 0.753601 0.058 Uiso 1 1 calc R U . . .
H28C H 0.824971 1.880353 0.700335 0.058 Uiso 1 1 calc R U . . .
C8 C 0.85768(15) 0.0245(3) 0.34082(11) 0.0437(6) Uani 1 1 d . . . . .
H8A H 0.902778 0.077423 0.318654 0.066 Uiso 1 1 calc R U . . .
H8B H 0.843851 -0.098085 0.327198 0.066 Uiso 1 1 calc R U . . .
H8C H 0.885142 0.024544 0.383793 0.066 Uiso 1 1 calc R U . . .
C5 C 0.67412(17) -0.3843(3) 0.32753(10) 0.0429(6) Uani 1 1 d . . . . .
H5A H 0.675420 -0.459858 0.292579 0.064 Uiso 1 1 calc R U . . .
H5B H 0.635547 -0.441236 0.353292 0.064 Uiso 1 1 calc R U . . .
H5C H 0.738836 -0.367601 0.350125 0.064 Uiso 1 1 calc R U . . .
C25 C 1.03071(15) 1.4317(3) 0.67025(12) 0.0497(6) Uani 1 1 d . . . . .
H25A H 1.018440 1.406905 0.627109 0.075 Uiso 1 1 calc R U . . .
H25B H 1.096288 1.399917 0.687815 0.075 Uiso 1 1 calc R U . . .
H25C H 1.020763 1.558629 0.676754 0.075 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 1.238(2) . ?
O2 C30 1.232(2) . ?
N1 H1 0.8800 . ?
N1 C2 1.379(3) . ?
N1 C9 1.353(3) . ?
N2 H2 0.8800 . ?
N2 C29 1.373(3) . ?
N2 C22 1.360(2) . ?
N005 H005 0.8800 . ?
N005 C14 1.379(3) . ?
N005 C17 1.383(2) . ?
C2 C3 1.401(3) . ?
C2 C1 1.415(3) . ?
C6 C3 1.399(3) . ?
C6 C9 1.409(3) . ?
C6 C7 1.503(3) . ?
C3 C4 1.505(3) . ?
C14 C13 1.410(3) . ?
C14 C15 1.390(3) . ?
C13 C16 1.445(3) . ?
C13 C12 1.386(3) . ?
C10 C15 1.394(3) . ?
C10 C9 1.469(3) . ?
C10 C11 1.414(3) . ?
C29 C26 1.399(3) . ?
C29 C30 1.425(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.408(3) . ?
C16 C21 1.397(3) . ?
C19 C22 1.466(3) . ?
C19 C18 1.391(3) . ?
C19 C20 1.408(3) . ?
C17 C18 1.386(3) . ?
C1 H1A 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C23 C22 1.402(3) . ?
C23 C26 1.406(3) . ?
C23 C24 1.506(3) . ?
C12 H12 0.9500 . ?
C26 C27 1.504(3) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.524(3) . ?
C21 H21 0.9500 . ?
C30 H30 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.522(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.523(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C2 N1 H1 125.2 . . ?
C9 N1 H1 125.2 . . ?
C9 N1 C2 109.55(16) . . ?
C29 N2 H2 124.8 . . ?
C22 N2 H2 124.8 . . ?
C22 N2 C29 110.33(15) . . ?
C14 N005 H005 125.6 . . ?
C14 N005 C17 108.83(16) . . ?
C17 N005 H005 125.6 . . ?
N1 C2 C3 107.65(17) . . ?
N1 C2 C1 123.69(18) . . ?
C3 C2 C1 128.62(18) . . ?
C3 C6 C9 107.02(17) . . ?
C3 C6 C7 125.79(18) . . ?
C9 C6 C7 127.16(18) . . ?
C2 C3 C4 126.22(18) . . ?
C6 C3 C2 107.45(17) . . ?
C6 C3 C4 126.32(18) . . ?
N005 C14 C13 109.04(16) . . ?
N005 C14 C15 128.63(18) . . ?
C15 C14 C13 122.32(18) . . ?
C14 C13 C16 106.53(17) . . ?
C12 C13 C14 118.83(18) . . ?
C12 C13 C16 134.63(18) . . ?
C15 C10 C9 119.81(17) . . ?
C15 C10 C11 119.88(17) . . ?
C11 C10 C9 120.31(18) . . ?
N2 C29 C26 107.35(17) . . ?
N2 C29 C30 122.48(17) . . ?
C26 C29 C30 130.16(18) . . ?
C14 C15 C10 118.04(17) . . ?
C14 C15 H15 121.0 . . ?
C10 C15 H15 121.0 . . ?
C17 C16 C13 106.52(17) . . ?
C21 C16 C13 134.78(19) . . ?
C21 C16 C17 118.69(18) . . ?
C18 C19 C22 118.64(18) . . ?
C18 C19 C20 119.42(18) . . ?
C20 C19 C22 121.94(18) . . ?
N005 C17 C16 109.08(17) . . ?
N005 C17 C18 128.70(18) . . ?
C18 C17 C16 122.21(17) . . ?
O1 C1 C2 126.76(19) . . ?
O1 C1 H1A 116.6 . . ?
C2 C1 H1A 116.6 . . ?
N1 C9 C6 108.32(16) . . ?
N1 C9 C10 122.10(17) . . ?
C6 C9 C10 129.53(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.12(19) . . ?
C12 C11 H11 119.4 . . ?
C22 C23 C26 107.43(17) . . ?
C22 C23 C24 126.92(18) . . ?
C26 C23 C24 125.65(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.74(19) . . ?
C11 C12 H12 120.1 . . ?
N2 C22 C19 120.19(16) . . ?
N2 C22 C23 107.53(17) . . ?
C23 C22 C19 132.13(18) . . ?
C29 C26 C23 107.34(17) . . ?
C29 C26 C27 125.76(19) . . ?
C23 C26 C27 126.89(18) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 C19 118.71(18) . . ?
C17 C18 H18 120.6 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.67(18) . . ?
C21 C20 H20 119.2 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.46(16) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C16 C21 H21 120.4 . . ?
C20 C21 C16 119.24(19) . . ?
C20 C21 H21 120.4 . . ?
O2 C30 C29 125.44(19) . . ?
O2 C30 H30 117.3 . . ?
C29 C30 H30 117.3 . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
C26 C27 C28 112.61(17) . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C6 C7 C8 113.34(17) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C23 C24 C25 113.01(19) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 C2 C3 C6 0.4(2) . . . . ?
N1 C2 C3 C4 179.29(17) . . . . ?
N1 C2 C1 O1 0.0(3) . . . . ?
N2 C29 C26 C23 1.1(2) . . . . ?
N2 C29 C26 C27 -179.56(18) . . . . ?
N2 C29 C30 O2 -2.7(3) . . . . ?
N005 C14 C13 C16 -0.4(2) . . . . ?
N005 C14 C13 C12 178.40(17) . . . . ?
N005 C14 C15 C10 -178.56(18) . . . . ?
N005 C17 C18 C19 -178.12(18) . . . . ?
C2 N1 C9 C6 1.0(2) . . . . ?
C2 N1 C9 C10 178.74(16) . . . . ?
C2 C3 C4 C5 -72.3(3) . . . . ?
C6 C3 C4 C5 106.4(2) . . . . ?
C3 C2 C1 O1 177.30(19) . . . . ?
C3 C6 C9 N1 -0.8(2) . . . . ?
C3 C6 C9 C10 -178.26(18) . . . . ?
C3 C6 C7 C8 -79.7(2) . . . . ?
C14 N005 C17 C16 0.9(2) . . . . ?
C14 N005 C17 C18 -178.32(18) . . . . ?
C14 C13 C16 C17 0.9(2) . . . . ?
C14 C13 C16 C21 -178.0(2) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
C13 C14 C15 C10 2.3(3) . . . . ?
C13 C16 C17 N005 -1.1(2) . . . . ?
C13 C16 C17 C18 178.14(17) . . . . ?
C13 C16 C21 C20 179.9(2) . . . . ?
C10 C11 C12 C13 2.2(3) . . . . ?
C29 N2 C22 C19 176.24(17) . . . . ?
C29 N2 C22 C23 0.1(2) . . . . ?
C29 C26 C27 C28 -82.0(3) . . . . ?
C15 C14 C13 C16 178.85(17) . . . . ?
C15 C14 C13 C12 -2.3(3) . . . . ?
C15 C10 C9 N1 -33.5(3) . . . . ?
C15 C10 C9 C6 143.6(2) . . . . ?
C15 C10 C11 C12 -2.1(3) . . . . ?
C16 C13 C12 C11 178.4(2) . . . . ?
C16 C17 C18 C19 2.8(3) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C17 N005 C14 C13 -0.3(2) . . . . ?
C17 N005 C14 C15 -179.48(18) . . . . ?
C17 C16 C21 C20 1.0(3) . . . . ?
C1 C2 C3 C6 -177.28(18) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C9 N1 C2 C3 -0.9(2) . . . . ?
C9 N1 C2 C1 176.91(17) . . . . ?
C9 C6 C3 C2 0.2(2) . . . . ?
C9 C6 C3 C4 -178.66(17) . . . . ?
C9 C6 C7 C8 102.4(2) . . . . ?
C9 C10 C15 C14 -179.06(16) . . . . ?
C9 C10 C11 C12 176.81(18) . . . . ?
C11 C10 C15 C14 -0.1(3) . . . . ?
C11 C10 C9 N1 147.53(18) . . . . ?
C11 C10 C9 C6 -35.3(3) . . . . ?
C23 C26 C27 C28 97.2(2) . . . . ?
C12 C13 C16 C17 -177.6(2) . . . . ?
C12 C13 C16 C21 3.5(4) . . . . ?
C22 N2 C29 C26 -0.7(2) . . . . ?
C22 N2 C29 C30 178.22(18) . . . . ?
C22 C19 C18 C17 179.42(17) . . . . ?
C22 C19 C20 C21 178.94(18) . . . . ?
C22 C23 C26 C29 -1.1(2) . . . . ?
C22 C23 C26 C27 179.60(19) . . . . ?
C22 C23 C24 C25 96.4(3) . . . . ?
C26 C29 C30 O2 176.0(2) . . . . ?
C26 C23 C22 N2 0.6(2) . . . . ?
C26 C23 C22 C19 -174.9(2) . . . . ?
C26 C23 C24 C25 -83.5(3) . . . . ?
C18 C19 C22 N2 -33.2(3) . . . . ?
C18 C19 C22 C23 141.9(2) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C20 C19 C22 N2 147.38(19) . . . . ?
C20 C19 C22 C23 -37.5(3) . . . . ?
C20 C19 C18 C17 -1.1(3) . . . . ?
C21 C16 C17 N005 177.99(17) . . . . ?
C21 C16 C17 C18 -2.7(3) . . . . ?
C30 C29 C26 C23 -177.7(2) . . . . ?
C30 C29 C26 C27 1.6(3) . . . . ?
C7 C6 C3 C2 -178.00(17) . . . . ?
C7 C6 C3 C4 3.1(3) . . . . ?
C7 C6 C9 N1 177.41(17) . . . . ?
C7 C6 C9 C10 0.0(3) . . . . ?
C24 C23 C22 N2 -179.26(19) . . . . ?
C24 C23 C22 C19 5.2(4) . . . . ?
C24 C23 C26 C29 178.83(19) . . . . ?
C24 C23 C26 C27 -0.5(3) . . . . ?


_olex2_submission_original_sample_id F-5
_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_t
_database_code_depnum_ccdc_archive 'CCDC 2298888'
loop_
_audit_author_name
_audit_author_address
'Qing He'
;Hunan University
China
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        WF-X
_chemical_formula_moiety         'C18 H23 N2 O2, C18 H24 N2 O2'
_chemical_formula_sum            'C36 H47 N4 O4'
_chemical_formula_weight         599.80
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      2
_cell_length_a                   12.2720(2)
_cell_length_b                   12.5331(2)
_cell_length_c                   13.7088(2)
_cell_angle_alpha                72.2350(10)
_cell_angle_beta                 66.4510(10)
_cell_angle_gamma                65.2320(10)
_cell_volume                     1730.90(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7569
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      63.51
_cell_measurement_theta_min      3.94
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6692
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.8894.
The λ/2 correction factor is Not present.
;
_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    1.1507
_exptl_crystal_description       block
_exptl_crystal_F_000             647.9531
_exptl_crystal_preparation       'CHCl3/Isopropyl Ether'
_exptl_crystal_recrystallization_method 'CHCl3/Isopropyl Ether'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27340
_diffrn_reflns_theta_full        63.8129
_diffrn_reflns_theta_max         63.81
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3900
_reflns_number_total             5708
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.4248
_refine_diff_density_min         -0.5299
_refine_diff_density_rms         0.0615
_refine_ls_d_res_high            0.8591
_refine_ls_d_res_low             12.3939
_refine_ls_goodness_of_fit_ref   1.0440
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    88
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5708
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.0434
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)²+1.5251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1945
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5B-C4B
 1.5 with sigma of 0.01
 C22-C23A
 1.52 with sigma of 0.01
 C4B-C3 \\sim C7-C6
 with sigma of 0.02
 C22-C23A \\sim C23B-C22
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
4. Others
 Sof(H22)=Sof(C23A)=Sof(H23d)=Sof(H23e)=Sof(H23f)=Sof(H22c)=Sof(H22d)=1-FVAR(1)
 Sof(H22)=Sof(C23B)=Sof(H23a)=Sof(H23b)=Sof(H23c)=Sof(H22a)=Sof(H22b)=FVAR(1)
 Sof(C4A)=Sof(H4Aa)=Sof(H4Ab)=1-FVAR(2)
 Sof(C4B)=Sof(H4Ba)=Sof(H4Bb)=FVAR(2)
 Sof(C5A)=Sof(H5Aa)=Sof(H5Ab)=Sof(H5Ac)=1-FVAR(3)
 Sof(C5B)=Sof(H5Ba)=Sof(H5Bb)=Sof(H5Bc)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C30(H30a,H30b), C33(H33a,H33b), C7(H7a,H7b), C15(H15a,H15b),
 C4B(H4Ba,H4Bb), C4A(H4Aa,H4Ab), C22(H22a,H22b), C22(H22c,H22d)
5.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2), N1(H1), N3(H3), C36(H36), C18(H18), C1(H1a), C12(H12), C19(H19)
5.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C31(H31a,H31b,H31c), C34(H34a,H34b,H34c), C26(H26a,H26b,
 H26c), C23B(H23a,H23b,H23c), C16(H16a,H16b,H16c), C5B(H5Ba,H5Bb,H5Bc),
 C13(H13a,H13b,H13c), C23A(H23d,H23e,H23f), C5A(H5Aa,H5Ab,H5Ac)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
O2 O 0.8341(2) -0.10008(18) 0.73407(17) 0.0529(6) Uani 1.000000 . U .
O4 O -0.10183(19) 0.3353(2) 1.25926(19) 0.0631(7) Uani 1.000000 . U .
N4 N 0.1487(2) 0.3353(2) 1.13555(17) 0.0384(5) Uani 1.000000 . U .
H4 H 0.1518(2) 0.2622(2) 1.16794(17) 0.0461(7) Uiso 1.000000 R . .
O1 O 0.6233(2) 0.5603(2) 0.24234(17) 0.0653(7) Uani 1.000000 . U .
N2 N 0.7499(2) 0.0693(2) 0.56199(19) 0.0482(7) Uani 1.000000 . U .
H2 H 0.7064(2) 0.0977(2) 0.62283(19) 0.0579(8) Uiso 1.000000 R . .
N1 N 0.6506(2) 0.3310(2) 0.37516(19) 0.0536(7) Uani 1.000000 . U .
H1 H 0.7233(2) 0.3300(2) 0.32498(19) 0.0644(9) Uiso 1.000000 R . .
N3 N 0.4437(2) 0.2703(2) 0.93481(19) 0.0626(9) Uani 1.000000 . U .
H3 H 0.4194(2) 0.3158(2) 0.87894(19) 0.0752(10) Uiso 1.000000 R . .
C28 C 0.2500(2) 0.3688(2) 1.0690(2) 0.0386(6) Uani 1.000000 . U .
C35 C 0.0408(2) 0.4340(2) 1.1441(2) 0.0413(7) Uani 1.000000 . U .
O3 O 0.6286(3) 0.1874(3) 0.74162(18) 0.1122(14) Uani 1.000000 . U .
C27 C 0.3760(3) 0.2805(3) 1.0398(2) 0.0445(7) Uani 1.000000 . U .
C29 C 0.2077(3) 0.4919(3) 1.0355(2) 0.0444(7) Uani 1.000000 . U .
C24 C 0.4467(3) 0.1930(3) 1.1047(2) 0.0479(8) Uani 1.000000 . U .
C9 C 0.7317(3) 0.1250(3) 0.4644(2) 0.0520(8) Uani 1.000000 . U .
C32 C 0.0754(3) 0.5331(2) 1.0825(2) 0.0436(7) Uani 1.000000 . U .
C36 C -0.0811(3) 0.4274(3) 1.2042(2) 0.0513(8) Uani 1.000000 . U .
H36 H -0.1518(3) 0.4984(3) 1.2020(2) 0.0615(10) Uiso 1.000000 R . .
C25 C 0.4133(3) 0.1807(3) 1.2241(2) 0.0537(8) Uani 1.000000 . U .
H25a H 0.3203(3) 0.2120(3) 1.2562(2) 0.0644(10) Uiso 1.000000 R . .
H25b H 0.4434(3) 0.0953(3) 1.2553(2) 0.0644(10) Uiso 1.000000 R . .
C10 C 0.6308(3) 0.2388(3) 0.4556(2) 0.0576(9) Uani 1.000000 . U .
C2 C 0.8460(4) -0.0375(3) 0.5506(3) 0.0567(9) Uani 1.000000 . U .
C17 C 0.5395(3) 0.4258(3) 0.3846(2) 0.0608(10) Uani 1.000000 . U .
C21 C 0.5598(3) 0.1279(3) 1.0350(2) 0.0657(11) Uani 1.000000 . U .
C30 C 0.2904(3) 0.5663(3) 0.9711(3) 0.0658(10) Uani 1.000000 . U .
H30a H 0.3666(3) 0.5198(3) 0.9196(3) 0.0789(13) Uiso 1.000000 R . .
H30b H 0.2441(3) 0.6377(3) 0.9289(3) 0.0789(13) Uiso 1.000000 R . .
C33 C -0.0134(3) 0.6596(3) 1.0714(3) 0.0602(9) Uani 1.000000 . U .
H33a H 0.0254(3) 0.7054(3) 1.0029(3) 0.0723(11) Uiso 1.000000 R . .
H33b H -0.0926(3) 0.6603(3) 1.0677(3) 0.0723(11) Uiso 1.000000 R . .
C18 C 0.5326(3) 0.5376(3) 0.3158(3) 0.0654(11) Uani 1.000000 . U .
H18 H 0.4525(3) 0.5993(3) 0.3271(3) 0.0785(13) Uiso 1.000000 R . .
C1 C 0.8846(4) -0.1164(3) 0.6398(3) 0.0641(10) Uani 1.000000 . U .
H1a H 0.9550(4) -0.1873(3) 0.6252(3) 0.0769(12) Uiso 1.000000 R . .
C11 C 0.5031(3) 0.2743(4) 0.5177(3) 0.0724(12) Uani 1.000000 . U .
C6 C 0.8167(4) 0.0505(3) 0.3883(3) 0.0662(10) Uani 1.000000 D U .
C14 C 0.4456(3) 0.3918(4) 0.4733(3) 0.0731(12) Uani 1.000000 . U .
C22 C 0.6646(3) 0.0224(3) 1.0657(3) 0.0703(12) Uani 1.000000 D U .
C20 C 0.5561(3) 0.1776(3) 0.9298(2) 0.0772(14) Uani 1.000000 . U .
C3 C 0.8884(5) -0.0515(3) 0.4427(3) 0.0857(14) Uani 1.000000 D U .
C7 C 0.8183(5) 0.0710(4) 0.2724(3) 0.0869(14) Uani 1.000000 D U .
H7a H 0.8037(5) 0.0036(4) 0.2626(3) 0.1042(17) Uiso 1.000000 R . .
H7b H 0.7469(5) 0.1441(4) 0.2611(3) 0.1042(17) Uiso 1.000000 R . .
C15 C 0.3086(3) 0.4693(5) 0.5116(3) 0.0996(18) Uani 1.000000 . U .
H15a H 0.2762(3) 0.4505(5) 0.5913(3) 0.120(2) Uiso 1.000000 R . .
H15b H 0.3029(3) 0.5539(5) 0.4921(3) 0.120(2) Uiso 1.000000 R . .
C12 C 0.4388(4) 0.1977(5) 0.6124(4) 0.104(2) Uani 1.000000 . U .
H12 H 0.4227(4) 0.2026(5) 0.6850(4) 0.125(2) Uiso 1.000000 R . .
C19 C 0.6424(4) 0.1388(4) 0.8309(3) 0.111(2) Uani 1.000000 . U .
H19 H 0.7157(4) 0.0708(4) 0.8338(3) 0.133(3) Uiso 1.000000 R . .
C8 C 0.9365(5) 0.0835(5) 0.1881(3) 0.0990(16) Uani 1.000000 . U .
H8a H 0.9259(13) 0.104(3) 0.1167(4) 0.148(2) Uiso 1.000000 GR . .
H8b H 0.955(2) 0.147(2) 0.1994(18) 0.148(2) Uiso 1.000000 GR . .
H8c H 1.0065(9) 0.0081(11) 0.192(2) 0.148(2) Uiso 1.000000 GR . .
C31 C 0.3310(5) 0.6056(5) 1.0418(4) 0.1051(17) Uani 1.000000 . U .
H31a H 0.388(3) 0.650(3) 0.9962(5) 0.158(3) Uiso 1.000000 GR . .
H31b H 0.2562(6) 0.657(3) 1.089(2) 0.158(3) Uiso 1.000000 GR . .
H31c H 0.375(3) 0.5354(5) 1.086(2) 0.158(3) Uiso 1.000000 GR . .
C34 C -0.0445(5) 0.7199(4) 1.1640(4) 0.0994(16) Uani 1.000000 . U .
H34a H -0.105(3) 0.8007(13) 1.1546(17) 0.149(2) Uiso 1.000000 GR . .
H34b H -0.082(3) 0.6741(19) 1.2321(5) 0.149(2) Uiso 1.000000 GR . .
H34c H 0.0329(8) 0.724(3) 1.1653(19) 0.149(2) Uiso 1.000000 GR . .
C4B C 1.0267(13) -0.1556(7) 0.3871(7) 0.065(4) Uani 0.55(2) D U 1
H4Ba H 1.0648(13) -0.1268(7) 0.3100(7) 0.078(5) Uiso 0.55(2) R . 1
H4Bb H 1.0880(13) -0.1776(7) 0.4259(7) 0.078(5) Uiso 0.55(2) R . 1
C26 C 0.4720(6) 0.2476(6) 1.2519(4) 0.124(2) Uani 1.000000 . U .
H26a H 0.5639(7) 0.218(3) 1.218(3) 0.186(3) Uiso 1.000000 GR . .
H26b H 0.438(3) 0.3328(8) 1.225(3) 0.186(3) Uiso 1.000000 GR . .
H26c H 0.452(4) 0.235(4) 1.3304(5) 0.186(3) Uiso 1.000000 GR . .
C23B C 0.6539(6) -0.0823(5) 1.0760(6) 0.057(2) Uani 0.548(9) D U 1
H23a H 0.661(4) -0.0937(18) 1.0059(9) 0.086(3) Uiso 0.548(9) GR . 1
H23b H 0.721(3) -0.1464(5) 1.102(3) 0.086(3) Uiso 0.548(9) GR . 1
H23c H 0.5715(18) -0.0838(15) 1.128(3) 0.086(3) Uiso 0.548(9) GR . 1
C16 C 0.2265(5) 0.4524(6) 0.4639(7) 0.152(3) Uani 1.000000 . U .
H16a H 0.257(3) 0.473(5) 0.3851(7) 0.229(4) Uiso 1.000000 GR . .
H16b H 0.230(4) 0.3691(14) 0.484(4) 0.229(4) Uiso 1.000000 GR . .
H16c H 0.1390(11) 0.504(4) 0.491(4) 0.229(4) Uiso 1.000000 GR . .
C5B C 0.9870(14) -0.2586(11) 0.4004(14) 0.187(8) Uani 0.588(16) D U 1
H5Ba H 0.904(6) -0.2287(12) 0.390(11) 0.281(12) Uiso 0.588(16) GR . 1
H5Bb H 1.049(7) -0.310(6) 0.347(7) 0.281(12) Uiso 0.588(16) GR . 1
H5Bc H 0.982(12) -0.305(7) 0.473(4) 0.281(12) Uiso 0.588(16) GR . 1
C13 C 0.4049(8) 0.1201(6) 0.5866(5) 0.166(3) Uani 1.000000 . U .
H13a H 0.341(5) 0.1657(6) 0.550(5) 0.248(5) Uiso 1.000000 GR . .
H13b H 0.4796(14) 0.069(4) 0.539(5) 0.248(5) Uiso 1.000000 GR . .
H13c H 0.370(6) 0.071(4) 0.6527(7) 0.248(5) Uiso 1.000000 GR . .
C23A C 0.7799(6) 0.0403(7) 1.0221(6) 0.060(3) Uani 0.452(9) D U 2
H23d H 0.7742(16) 0.107(3) 1.049(3) 0.090(4) Uiso 0.452(9) GR . 2
H23e H 0.8452(11) -0.0321(18) 1.043(4) 0.090(4) Uiso 0.452(9) GR . 2
H23f H 0.802(2) 0.059(5) 0.9433(7) 0.090(4) Uiso 0.452(9) GR . 2
C4A C 0.9444(13) -0.1631(7) 0.4076(7) 0.046(3) Uani 0.45(2) . U 2
H4Aa H 0.9199(13) -0.2259(7) 0.4665(7) 0.055(4) Uiso 0.45(2) R . 2
H4Ab H 0.9201(13) -0.1592(7) 0.3456(7) 0.055(4) Uiso 0.45(2) R . 2
C5A C 1.0872(11) -0.1859(13) 0.3744(10) 0.059(4) Uani 0.412(16) . U 2
H5Aa H 1.1052(14) -0.114(2) 0.330(4) 0.089(5) Uiso 0.412(16) GR . 2
H5Ab H 1.1123(17) -0.207(5) 0.4392(10) 0.089(5) Uiso 0.412(16) GR . 2
H5Ac H 1.1349(11) -0.251(4) 0.333(4) 0.089(5) Uiso 0.412(16) GR . 2
H22a H 0.7460(3) 0.0247(3) 1.0103(3) 0.0844(14) Uiso 0.548(9) R . 1
H22b H 0.6669(3) 0.0291(3) 1.1350(3) 0.0844(14) Uiso 0.548(9) R . 1
H22c H 0.6425(3) 0.0047(3) 1.1454(3) 0.0844(14) Uiso 0.452(9) R . 2
H22d H 0.6725(3) -0.0477(3) 1.0411(3) 0.0844(14) Uiso 0.452(9) R . 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.230(4) . ?
O4 C36 1.236(4) . ?
N4 C28 1.361(3) . ?
N4 C35 1.375(3) . ?
O1 C18 1.237(4) . ?
N2 C9 1.365(4) . ?
N2 C2 1.365(4) . ?
N1 C10 1.362(4) . ?
N1 C17 1.372(4) . ?
N3 C27 1.358(4) . ?
N3 C20 1.374(4) . ?
C28 C27 1.455(4) . ?
C28 C29 1.396(4) . ?
C35 C32 1.397(4) . ?
C35 C36 1.415(4) . ?
O3 C19 1.234(4) . ?
C27 C24 1.404(4) . ?
C29 C32 1.408(4) . ?
C29 C30 1.502(4) . ?
C24 C25 1.495(4) . ?
C24 C21 1.404(4) . ?
C9 C10 1.455(5) . ?
C9 C6 1.400(5) . ?
C32 C33 1.504(4) . ?
C25 C26 1.512(6) . ?
C10 C11 1.400(4) . ?
C2 C1 1.425(4) . ?
C2 C3 1.398(5) . ?
C17 C18 1.420(5) . ?
C17 C14 1.402(4) . ?
C21 C22 1.500(4) . ?
C21 C20 1.397(4) . ?
C30 C31 1.520(7) . ?
C33 C34 1.511(6) . ?
C11 C14 1.400(5) . ?
C11 C12 1.512(5) . ?
C6 C3 1.402(5) . ?
C6 C7 1.522(5) . ?
C14 C15 1.511(5) . ?
C22 C23B 1.333(7) . ?
C22 C23A 1.385(6) . ?
C20 C19 1.421(5) . ?
C3 C4B 1.697(12) . ?
C3 C4A 1.414(8) . ?
C7 C8 1.485(7) . ?
C15 C16 1.509(8) . ?
C12 C13 1.383(9) . ?
C4B C5B 1.500(9) . ?
C4A C5A 1.544(15) . ?

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
C35 N4 C28 109.1(2) . . ?
C2 N2 C9 109.5(3) . . ?
C17 N1 C10 109.4(2) . . ?
C20 N3 C27 109.2(2) . . ?
C27 C28 N4 120.8(2) . . ?
C29 C28 N4 108.6(2) . . ?
C29 C28 C27 130.6(3) . . ?
C32 C35 N4 108.1(2) . . ?
C36 C35 N4 122.6(3) . . ?
C36 C35 C32 129.2(3) . . ?
C28 C27 N3 120.8(2) . . ?
C24 C27 N3 108.5(2) . . ?
C24 C27 C28 130.6(2) . . ?
C32 C29 C28 107.1(2) . . ?
C30 C29 C28 125.6(3) . . ?
C30 C29 C32 127.0(3) . . ?
C25 C24 C27 126.0(3) . . ?
C21 C24 C27 106.9(2) . . ?
C21 C24 C25 126.8(3) . . ?
C10 C9 N2 120.4(3) . . ?
C6 C9 N2 108.2(3) . . ?
C6 C9 C10 131.3(3) . . ?
C29 C32 C35 107.1(2) . . ?
C33 C32 C35 125.7(3) . . ?
C33 C32 C29 127.3(3) . . ?
C35 C36 O4 124.3(3) . . ?
C26 C25 C24 111.2(3) . . ?
C9 C10 N1 121.6(3) . . ?
C11 C10 N1 108.2(3) . . ?
C11 C10 C9 130.2(3) . . ?
C1 C2 N2 122.0(3) . . ?
C3 C2 N2 107.8(3) . . ?
C3 C2 C1 130.1(3) . . ?
C18 C17 N1 122.2(3) . . ?
C14 C17 N1 108.0(3) . . ?
C14 C17 C18 129.7(3) . . ?
C22 C21 C24 127.3(3) . . ?
C20 C21 C24 107.2(3) . . ?
C20 C21 C22 125.5(3) . . ?
C31 C30 C29 112.5(3) . . ?
C34 C33 C32 112.5(3) . . ?
C17 C18 O1 124.7(3) . . ?
C2 C1 O2 125.2(3) . . ?
C14 C11 C10 107.4(3) . . ?
C12 C11 C10 125.9(4) . . ?
C12 C11 C14 126.6(3) . . ?
C3 C6 C9 106.8(3) . . ?
C7 C6 C9 125.7(3) . . ?
C7 C6 C3 127.1(4) . . ?
C11 C14 C17 107.1(3) . . ?
C15 C14 C17 125.4(3) . . ?
C15 C14 C11 127.5(3) . . ?
C21 C20 N3 108.2(3) . . ?
C19 C20 N3 122.1(3) . . ?
C19 C20 C21 129.4(3) . . ?
C6 C3 C2 107.6(4) . . ?
C8 C7 C6 115.3(4) . . ?
C16 C15 C14 112.8(5) . . ?
C13 C12 C11 115.6(5) . . ?
C20 C19 O3 124.4(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C22 C23A 1 1.5200 0.0100 0.1349
C5B C4B 1 1.5000 0.0100 0.0000

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C22 C23A 1 2
C7 C6 1 1
C4B C3 1 1
C23B C22 1 2

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.6097 0.0874 0.0874
2 0.0200 1.3590 0.0261 0.0261

