# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_tat6_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 2219044'
loop_
_audit_author_name
_audit_author_address
'Chung-Hung Hsieh'
;Department of Chemistry, Tamkang Universoty
Taiwan
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H38 N4 O2'
_chemical_formula_weight         534.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   9.259(3)
_cell_length_b                   15.873(5)
_cell_length_c                   19.879(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.57(2)
_cell_angle_gamma                90.00
_cell_volume                     2902.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      3.295
_cell_measurement_theta_max      25.653

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8272
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33247
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.94
_reflns_number_total             5671
_reflns_number_gt                3120
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5671
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.2767
_refine_ls_wR_factor_gt          0.2104
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3957(2) -0.01667(13) 0.41852(10) 0.0566(6) Uani 1 1 d . . .
O2 O -0.1016(2) -0.01659(14) 0.41035(12) 0.0686(6) Uani 1 1 d . . .
N1 N 0.6619(2) 0.08799(13) 0.43818(12) 0.0478(6) Uani 1 1 d . . .
N2 N 1.2307(3) 0.78967(18) 0.72937(14) 0.0785(9) Uani 1 1 d . . .
N3 N 0.1578(2) 0.08846(14) 0.43709(12) 0.0494(6) Uani 1 1 d . . .
N4 N 0.7033(4) 0.79161(19) 0.73659(16) 0.0923(10) Uani 1 1 d . . .
C1 C 0.4728(3) 0.01147(18) 0.36526(14) 0.0562(7) Uani 1 1 d . . .
H1A H 0.4040 0.0177 0.3236 0.067 Uiso 1 1 calc R . .
H1B H 0.5455 -0.0317 0.3564 0.067 Uiso 1 1 calc R . .
C2 C 0.5491(3) 0.09399(18) 0.38064(14) 0.0525(7) Uani 1 1 d . . .
H2A H 0.5936 0.1128 0.3402 0.063 Uiso 1 1 calc R . .
H2B H 0.4769 0.1369 0.3905 0.063 Uiso 1 1 calc R . .
C3 C 0.7121(3) 0.17133(16) 0.46124(13) 0.0475(7) Uani 1 1 d . . .
H3A H 0.6275 0.2053 0.4714 0.057 Uiso 1 1 calc R . .
H3B H 0.7564 0.1999 0.4244 0.057 Uiso 1 1 calc R . .
C4 C 0.8220(3) 0.16781(16) 0.52356(14) 0.0491(7) Uani 1 1 d . . .
H4A H 0.7787 0.1363 0.5592 0.059 Uiso 1 1 calc R . .
H4B H 0.9076 0.1356 0.5124 0.059 Uiso 1 1 calc R . .
C5 C 0.8735(3) 0.25203(15) 0.55203(13) 0.0449(6) Uani 1 1 d . . .
C6 C 0.8500(3) 0.32711(17) 0.51668(14) 0.0533(7) Uani 1 1 d . . .
H6 H 0.8009 0.3263 0.4720 0.064 Uiso 1 1 calc R . .
C7 C 0.8970(3) 0.40326(17) 0.54533(14) 0.0540(7) Uani 1 1 d . . .
H7 H 0.8791 0.4536 0.5199 0.065 Uiso 1 1 calc R . .
C8 C 0.9699(3) 0.40774(15) 0.61047(13) 0.0450(6) Uani 1 1 d . . .
C9 C 1.0220(3) 0.48883(16) 0.64031(13) 0.0452(6) Uani 1 1 d . . .
C10 C 0.9459(3) 0.56345(18) 0.62462(14) 0.0555(7) Uani 1 1 d . . .
H10 H 0.8560 0.5613 0.5963 0.067 Uiso 1 1 calc R . .
C11 C 0.9978(3) 0.64007(18) 0.64912(15) 0.0597(8) Uani 1 1 d . . .
H11 H 0.9438 0.6899 0.6377 0.072 Uiso 1 1 calc R . .
C12 C 1.1286(3) 0.64466(17) 0.69045(13) 0.0507(7) Uani 1 1 d . . .
C13 C 1.1859(3) 0.7253(2) 0.71354(14) 0.0592(8) Uani 1 1 d . . .
C14 C 1.2031(3) 0.57116(19) 0.70858(15) 0.0616(8) Uani 1 1 d . . .
H14 H 1.2913 0.5734 0.7381 0.074 Uiso 1 1 calc R . .
C15 C 1.1500(3) 0.49478(18) 0.68404(15) 0.0605(8) Uani 1 1 d . . .
H15 H 1.2021 0.4448 0.6973 0.073 Uiso 1 1 calc R . .
C16 C 0.9966(3) 0.33214(18) 0.64495(14) 0.0596(8) Uani 1 1 d . . .
H16 H 1.0484 0.3325 0.6891 0.072 Uiso 1 1 calc R . .
C17 C 0.9492(3) 0.25657(18) 0.61615(14) 0.0582(8) Uani 1 1 d . . .
H17 H 0.9691 0.2060 0.6411 0.070 Uiso 1 1 calc R . .
C18 C -0.0207(3) 0.01227(19) 0.35874(16) 0.0623(8) Uani 1 1 d . . .
H18A H -0.0867 0.0191 0.3163 0.075 Uiso 1 1 calc R . .
H18B H 0.0530 -0.0307 0.3506 0.075 Uiso 1 1 calc R . .
C19 C 0.0541(3) 0.09412(18) 0.37621(15) 0.0571(7) Uani 1 1 d . . .
H19A H 0.1058 0.1124 0.3378 0.069 Uiso 1 1 calc R . .
H19B H -0.0197 0.1374 0.3831 0.069 Uiso 1 1 calc R . .
C20 C 0.2048(3) 0.17189(16) 0.46209(14) 0.0526(7) Uani 1 1 d . . .
H20A H 0.1179 0.2062 0.4682 0.063 Uiso 1 1 calc R . .
H20B H 0.2572 0.2001 0.4277 0.063 Uiso 1 1 calc R . .
C21 C 0.3026(3) 0.16883(17) 0.52845(15) 0.0553(7) Uani 1 1 d . . .
H21A H 0.2475 0.1439 0.5634 0.066 Uiso 1 1 calc R . .
H21B H 0.3855 0.1310 0.5230 0.066 Uiso 1 1 calc R . .
C22 C 0.3612(3) 0.25274(16) 0.55338(13) 0.0465(6) Uani 1 1 d . . .
C23 C 0.4933(3) 0.25781(18) 0.59386(14) 0.0587(8) Uani 1 1 d . . .
H23 H 0.5468 0.2076 0.6046 0.070 Uiso 1 1 calc R . .
C24 C 0.5496(3) 0.33330(18) 0.61908(15) 0.0581(8) Uani 1 1 d . . .
H24 H 0.6402 0.3340 0.6469 0.070 Uiso 1 1 calc R . .
C25 C 0.4751(3) 0.40888(16) 0.60426(13) 0.0460(6) Uani 1 1 d . . .
C26 C 0.5294(3) 0.49034(16) 0.63260(13) 0.0471(6) Uani 1 1 d . . .
C27 C 0.4981(3) 0.56527(18) 0.59724(15) 0.0615(8) Uani 1 1 d . . .
H27 H 0.4456 0.5633 0.5533 0.074 Uiso 1 1 calc R . .
C28 C 0.5416(3) 0.64175(18) 0.62461(16) 0.0653(9) Uani 1 1 d . . .
H28 H 0.5184 0.6920 0.5998 0.078 Uiso 1 1 calc R . .
C29 C 0.6198(3) 0.64592(18) 0.68890(14) 0.0545(7) Uani 1 1 d . . .
C30 C 0.6656(4) 0.7266(2) 0.71636(16) 0.0680(9) Uani 1 1 d . . .
C31 C 0.3438(3) 0.40295(18) 0.56350(16) 0.0614(8) Uani 1 1 d . . .
H31 H 0.2900 0.4530 0.5523 0.074 Uiso 1 1 calc R . .
C32 C 0.2883(3) 0.32735(18) 0.53863(16) 0.0626(8) Uani 1 1 d . . .
H32 H 0.1980 0.3265 0.5107 0.075 Uiso 1 1 calc R . .
C33 C 0.6553(3) 0.57192(19) 0.72390(14) 0.0577(8) Uani 1 1 d . . .
H33 H 0.7105 0.5739 0.7672 0.069 Uiso 1 1 calc R . .
C34 C 0.6108(3) 0.49593(18) 0.69621(14) 0.0551(7) Uani 1 1 d . . .
H34 H 0.6360 0.4457 0.7208 0.066 Uiso 1 1 calc R . .
H4 H 0.329(4) 0.019(2) 0.4271(19) 0.088(12) Uiso 1 1 d . . .
H3 H -0.174(5) 0.018(2) 0.418(2) 0.097(13) Uiso 1 1 d . . .
H2 H 0.616(3) 0.0632(18) 0.4744(15) 0.064(9) Uiso 1 1 d . . .
H1 H 0.117(3) 0.0612(18) 0.4711(14) 0.056(8) Uiso 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
O1 C1 1.415(3) . ?
O1 H4 0.87(4) . ?
O2 C18 1.414(4) . ?
O2 H3 0.89(4) . ?
N1 C3 1.458(3) . ?
N1 C2 1.461(3) . ?
N2 C13 1.133(4) . ?
N3 C20 1.463(3) . ?
N3 C19 1.459(3) . ?
N4 C30 1.147(4) . ?
C1 C2 1.503(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.512(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.508(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C17 1.384(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9500 . ?
C8 C16 1.390(4) . ?
C8 C9 1.475(4) . ?
C9 C15 1.390(4) . ?
C9 C10 1.395(4) . ?
C10 C11 1.376(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 C14 1.382(4) . ?
C12 C13 1.441(4) . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.494(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.513(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.501(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C32 1.378(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.378(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.398(4) . ?
C24 H24 0.9500 . ?
C25 C31 1.385(4) . ?
C25 C26 1.475(4) . ?
C26 C34 1.399(4) . ?
C26 C27 1.395(4) . ?
C27 C28 1.372(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.396(4) . ?
C28 H28 0.9500 . ?
C29 C33 1.385(4) . ?
C29 C30 1.437(4) . ?
C31 C32 1.375(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.369(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H4 112(2) . . ?
C18 O2 H3 113(3) . . ?
C3 N1 C2 111.1(2) . . ?
C20 N3 C19 111.6(2) . . ?
O1 C1 C2 112.8(2) . . ?
O1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
O1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 C1 112.3(2) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 C4 112.6(2) . . ?
N1 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 115.4(2) . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C17 C5 C6 117.1(2) . . ?
C17 C5 C4 119.8(2) . . ?
C6 C5 C4 123.1(2) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C16 117.1(2) . . ?
C7 C8 C9 121.3(2) . . ?
C16 C8 C9 121.5(2) . . ?
C15 C9 C10 117.1(2) . . ?
C15 C9 C8 121.8(2) . . ?
C10 C9 C8 121.1(2) . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C14 119.1(2) . . ?
C11 C12 C13 120.0(3) . . ?
C14 C12 C13 120.8(3) . . ?
N2 C13 C12 177.6(3) . . ?
C15 C14 C12 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C12 C14 H14 119.9 . . ?
C14 C15 C9 121.7(3) . . ?
C14 C15 H15 119.1 . . ?
C9 C15 H15 119.1 . . ?
C17 C16 C8 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C8 C16 H16 119.5 . . ?
C16 C17 C5 122.1(2) . . ?
C16 C17 H17 119.0 . . ?
C5 C17 H17 119.0 . . ?
O2 C18 C19 112.5(3) . . ?
O2 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
O2 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
N3 C19 C18 112.5(2) . . ?
N3 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N3 C20 C21 113.1(2) . . ?
N3 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N3 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 114.6(2) . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C32 C22 C23 116.8(2) . . ?
C32 C22 C21 122.9(2) . . ?
C23 C22 C21 120.3(2) . . ?
C24 C23 C22 122.2(3) . . ?
C24 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C23 C24 C25 120.8(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C31 C25 C24 116.3(2) . . ?
C31 C25 C26 121.4(2) . . ?
C24 C25 C26 122.2(2) . . ?
C34 C26 C27 117.4(2) . . ?
C34 C26 C25 121.7(2) . . ?
C27 C26 C25 120.9(2) . . ?
C28 C27 C26 121.3(3) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C29 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C33 C29 C28 119.2(3) . . ?
C33 C29 C30 121.5(3) . . ?
C28 C29 C30 119.3(3) . . ?
N4 C30 C29 178.1(4) . . ?
C25 C31 C32 122.4(3) . . ?
C25 C31 H31 118.8 . . ?
C32 C31 H31 118.8 . . ?
C22 C32 C31 121.4(3) . . ?
C22 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C34 C33 C29 120.1(3) . . ?
C34 C33 H33 119.9 . . ?
C29 C33 H33 119.9 . . ?
C33 C34 C26 121.7(3) . . ?
C33 C34 H34 119.2 . . ?
C26 C34 H34 119.2 . . ?

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
C3 N1 C2 C1 -167.7(2) . . . . ?
O1 C1 C2 N1 63.8(3) . . . . ?
C2 N1 C3 C4 176.3(2) . . . . ?
N1 C3 C4 C5 -177.4(2) . . . . ?
C3 C4 C5 C17 166.4(3) . . . . ?
C3 C4 C5 C6 -14.2(4) . . . . ?
C17 C5 C6 C7 -1.7(4) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C16 1.5(4) . . . . ?
C6 C7 C8 C9 178.9(2) . . . . ?
C7 C8 C9 C15 -145.6(3) . . . . ?
C16 C8 C9 C15 31.7(4) . . . . ?
C7 C8 C9 C10 33.1(4) . . . . ?
C16 C8 C9 C10 -149.6(3) . . . . ?
C15 C9 C10 C11 2.5(4) . . . . ?
C8 C9 C10 C11 -176.3(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C14 -2.3(4) . . . . ?
C10 C11 C12 C13 177.2(3) . . . . ?
C11 C12 C13 N2 -55(8) . . . . ?
C14 C12 C13 N2 124(8) . . . . ?
C11 C12 C14 C15 2.0(4) . . . . ?
C13 C12 C14 C15 -177.5(3) . . . . ?
C12 C14 C15 C9 0.6(5) . . . . ?
C10 C9 C15 C14 -2.8(4) . . . . ?
C8 C9 C15 C14 176.0(3) . . . . ?
C7 C8 C16 C17 -1.7(4) . . . . ?
C9 C8 C16 C17 -179.0(3) . . . . ?
C8 C16 C17 C5 0.1(5) . . . . ?
C6 C5 C17 C16 1.6(4) . . . . ?
C4 C5 C17 C16 -178.9(3) . . . . ?
C20 N3 C19 C18 -167.0(2) . . . . ?
O2 C18 C19 N3 60.9(3) . . . . ?
C19 N3 C20 C21 175.2(2) . . . . ?
N3 C20 C21 C22 176.1(2) . . . . ?
C20 C21 C22 C32 28.7(4) . . . . ?
C20 C21 C22 C23 -152.1(3) . . . . ?
C32 C22 C23 C24 0.7(4) . . . . ?
C21 C22 C23 C24 -178.5(3) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C31 0.1(4) . . . . ?
C23 C24 C25 C26 177.5(3) . . . . ?
C31 C25 C26 C34 146.5(3) . . . . ?
C24 C25 C26 C34 -30.8(4) . . . . ?
C31 C25 C26 C27 -32.0(4) . . . . ?
C24 C25 C26 C27 150.7(3) . . . . ?
C34 C26 C27 C28 -2.0(4) . . . . ?
C25 C26 C27 C28 176.6(3) . . . . ?
C26 C27 C28 C29 0.5(5) . . . . ?
C27 C28 C29 C33 1.3(5) . . . . ?
C27 C28 C29 C30 179.4(3) . . . . ?
C33 C29 C30 N4 133(11) . . . . ?
C28 C29 C30 N4 -45(11) . . . . ?
C24 C25 C31 C32 0.0(4) . . . . ?
C26 C25 C31 C32 -177.5(3) . . . . ?
C23 C22 C32 C31 -0.6(4) . . . . ?
C21 C22 C32 C31 178.6(3) . . . . ?
C25 C31 C32 C22 0.3(5) . . . . ?
C28 C29 C33 C34 -1.6(4) . . . . ?
C30 C29 C33 C34 -179.6(3) . . . . ?
C29 C33 C34 C26 0.0(4) . . . . ?
C27 C26 C34 C33 1.7(4) . . . . ?
C25 C26 C34 C33 -176.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.94
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.109
####################################################################### 
# 
# 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_tat21b_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 2219045'
loop_
_audit_author_name
_audit_author_address
'Chung-Hung Hsieh'
;Department of Chemistry, Tamkang Universoty
Taiwan
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   9.161
_cell_length_b                   6.008
_cell_length_c                   28.752
_cell_angle_alpha                90.00
_cell_angle_beta                 90.32
_cell_angle_gamma                90.00
_cell_volume                     1582.5
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7818
_cell_measurement_theta_min      2.826
_cell_measurement_theta_max      28.327

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17358
_diffrn_reflns_av_R_equivalents  0.1345
_diffrn_reflns_av_sigmaI/netI    0.0908
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         28.39
_reflns_number_total             3900
_reflns_number_gt                2815
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0796P)²+3.5666P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3900
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.2571
_refine_ls_wR_factor_gt          0.2161
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5418(4) -0.5639(5) 0.78916(12) 0.0227(7) Uani 1 1 d . . .
H2 H 0.6130 -0.6875 0.7912 0.027 Uiso 1 1 calc R . .
H3 H 0.5438 -0.4831 0.8192 0.027 Uiso 1 1 calc R . .
C2 C 0.5871(3) -0.4066(5) 0.75056(11) 0.0223(7) Uani 1 1 d . . .
H4 H 0.5896 -0.4893 0.7208 0.027 Uiso 1 1 calc R . .
H5 H 0.6868 -0.3511 0.7571 0.027 Uiso 1 1 calc R . .
C3 C 0.4837(4) -0.2090(5) 0.74560(10) 0.0194(7) Uani 1 1 d . . .
H6 H 0.3819 -0.2638 0.7471 0.023 Uiso 1 1 calc R . .
H7 H 0.4992 -0.1074 0.7723 0.023 Uiso 1 1 calc R . .
C4 C 0.5027(3) -0.0781(5) 0.70078(11) 0.0197(6) Uani 1 1 d . . .
H8 H 0.6013 -0.0107 0.7001 0.024 Uiso 1 1 calc R . .
H9 H 0.4934 -0.1795 0.6738 0.024 Uiso 1 1 calc R . .
C5 C 0.4006(3) 0.2275(5) 0.65435(10) 0.0205(7) Uani 1 1 d . . .
H10 H 0.3907 0.1273 0.6272 0.025 Uiso 1 1 calc R . .
H11 H 0.4967 0.3024 0.6525 0.025 Uiso 1 1 calc R . .
C6 C 0.2796(4) 0.3997(6) 0.65355(11) 0.0235(7) Uani 1 1 d . . .
H12 H 0.1850 0.3203 0.6538 0.028 Uiso 1 1 calc R . .
H13 H 0.2860 0.4875 0.6826 0.028 Uiso 1 1 calc R . .
C7 C 0.2785(3) 0.5602(5) 0.61308(10) 0.0188(6) Uani 1 1 d . . .
C8 C 0.3865(4) 0.5671(6) 0.57862(11) 0.0235(7) Uani 1 1 d . . .
H14 H 0.4673 0.4683 0.5804 0.028 Uiso 1 1 calc R . .
C9 C 0.3763(4) 0.7167(6) 0.54207(11) 0.0229(7) Uani 1 1 d . . .
H15 H 0.4504 0.7177 0.5191 0.028 Uiso 1 1 calc R . .
C10 C 0.2606(3) 0.8652(5) 0.53811(10) 0.0196(7) Uani 1 1 d . . .
C11 C 0.2452(3) 1.0206(5) 0.49824(10) 0.0196(7) Uani 1 1 d . . .
C12 C 0.2906(4) 0.9598(6) 0.45352(11) 0.0250(7) Uani 1 1 d . . .
H16 H 0.3329 0.8173 0.4488 0.030 Uiso 1 1 calc R . .
C13 C 0.2751(4) 1.1033(6) 0.41623(11) 0.0246(7) Uani 1 1 d . . .
H17 H 0.3049 1.0582 0.3861 0.030 Uiso 1 1 calc R . .
C14 C 0.2157(4) 1.3135(6) 0.42296(11) 0.0233(7) Uani 1 1 d . . .
C15 C 0.2036(4) 1.4690(6) 0.38467(12) 0.0258(7) Uani 1 1 d . . .
C16 C 0.1536(4) 0.8615(6) 0.57306(11) 0.0216(7) Uani 1 1 d . . .
H18 H 0.0738 0.9622 0.5716 0.026 Uiso 1 1 calc R . .
C17 C 0.1641(4) 0.7122(6) 0.60939(11) 0.0222(7) Uani 1 1 d . . .
H19 H 0.0909 0.7131 0.6327 0.027 Uiso 1 1 calc R . .
C18 C 0.1691(4) 1.3777(6) 0.46702(11) 0.0248(7) Uani 1 1 d . . .
H20 H 0.1271 1.5205 0.4716 0.030 Uiso 1 1 calc R . .
C19 C 0.1844(4) 1.2323(6) 0.50392(11) 0.0246(7) Uani 1 1 d . . .
H21 H 0.1528 1.2773 0.5339 0.030 Uiso 1 1 calc R . .
H1 H 0.393(5) -0.733(7) 0.7589(15) 0.037 Uiso 1 1 d . . .
H22 H 0.298(5) 0.025(7) 0.6975(13) 0.036(11) Uiso 1 1 d . . .
N1 N 0.3920(3) 0.0971(4) 0.69765(9) 0.0182(6) Uani 1 1 d . . .
N2 N 0.1954(4) 1.5959(6) 0.35519(11) 0.0380(8) Uani 1 1 d . . .
O1 O 0.4003(2) -0.6531(4) 0.78183(8) 0.0223(5) 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 O1 1.417(4) . ?
C1 C2 1.517(4) . ?
C1 H2 0.9900 . ?
C1 H3 0.9900 . ?
C2 C3 1.525(4) . ?
C2 H4 0.9900 . ?
C2 H5 0.9900 . ?
C3 C4 1.521(4) . ?
C3 H6 0.9900 . ?
C3 H7 0.9900 . ?
C4 N1 1.465(4) . ?
C4 H8 0.9900 . ?
C4 H9 0.9900 . ?
C5 N1 1.473(4) . ?
C5 C6 1.517(5) . ?
C5 H10 0.9900 . ?
C5 H11 0.9900 . ?
C6 C7 1.511(4) . ?
C6 H12 0.9900 . ?
C6 H13 0.9900 . ?
C7 C17 1.393(5) . ?
C7 C8 1.405(4) . ?
C8 C9 1.386(4) . ?
C8 H14 0.9500 . ?
C9 C10 1.389(5) . ?
C9 H15 0.9500 . ?
C10 C16 1.408(4) . ?
C10 C11 1.484(4) . ?
C11 C19 1.399(5) . ?
C11 C12 1.402(4) . ?
C12 C13 1.382(4) . ?
C12 H16 0.9500 . ?
C13 C14 1.389(5) . ?
C13 H17 0.9500 . ?
C14 C18 1.394(5) . ?
C14 C15 1.447(5) . ?
C15 N2 1.142(4) . ?
C16 C17 1.380(4) . ?
C16 H18 0.9500 . ?
C17 H19 0.9500 . ?
C18 C19 1.380(5) . ?
C18 H20 0.9500 . ?
C19 H21 0.9500 . ?
N1 H22 0.96(4) . ?
O1 H1 0.82(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 112.3(3) . . ?
O1 C1 H2 109.1 . . ?
C2 C1 H2 109.1 . . ?
O1 C1 H3 109.1 . . ?
C2 C1 H3 109.1 . . ?
H2 C1 H3 107.9 . . ?
C1 C2 C3 112.4(3) . . ?
C1 C2 H4 109.1 . . ?
C3 C2 H4 109.1 . . ?
C1 C2 H5 109.1 . . ?
C3 C2 H5 109.1 . . ?
H4 C2 H5 107.9 . . ?
C4 C3 C2 114.1(3) . . ?
C4 C3 H6 108.7 . . ?
C2 C3 H6 108.7 . . ?
C4 C3 H7 108.7 . . ?
C2 C3 H7 108.7 . . ?
H6 C3 H7 107.6 . . ?
N1 C4 C3 109.9(2) . . ?
N1 C4 H8 109.7 . . ?
C3 C4 H8 109.7 . . ?
N1 C4 H9 109.7 . . ?
C3 C4 H9 109.7 . . ?
H8 C4 H9 108.2 . . ?
N1 C5 C6 109.4(2) . . ?
N1 C5 H10 109.8 . . ?
C6 C5 H10 109.8 . . ?
N1 C5 H11 109.8 . . ?
C6 C5 H11 109.8 . . ?
H10 C5 H11 108.2 . . ?
C7 C6 C5 116.7(3) . . ?
C7 C6 H12 108.1 . . ?
C5 C6 H12 108.1 . . ?
C7 C6 H13 108.1 . . ?
C5 C6 H13 108.1 . . ?
H12 C6 H13 107.3 . . ?
C17 C7 C8 117.3(3) . . ?
C17 C7 C6 118.6(3) . . ?
C8 C7 C6 124.1(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H14 119.7 . . ?
C7 C8 H14 119.7 . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 H15 119.1 . . ?
C10 C9 H15 119.1 . . ?
C9 C10 C16 117.7(3) . . ?
C9 C10 C11 122.5(3) . . ?
C16 C10 C11 119.8(3) . . ?
C19 C11 C12 117.6(3) . . ?
C19 C11 C10 121.2(3) . . ?
C12 C11 C10 121.1(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H16 119.4 . . ?
C11 C12 H16 119.4 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H17 120.1 . . ?
C14 C13 H17 120.1 . . ?
C13 C14 C18 120.0(3) . . ?
C13 C14 C15 120.6(3) . . ?
C18 C14 C15 119.4(3) . . ?
N2 C15 C14 178.2(4) . . ?
C17 C16 C10 120.3(3) . . ?
C17 C16 H18 119.8 . . ?
C10 C16 H18 119.8 . . ?
C16 C17 C7 122.2(3) . . ?
C16 C17 H19 118.9 . . ?
C7 C17 H19 118.9 . . ?
C19 C18 C14 119.6(3) . . ?
C19 C18 H20 120.2 . . ?
C14 C18 H20 120.2 . . ?
C18 C19 C11 121.6(3) . . ?
C18 C19 H21 119.2 . . ?
C11 C19 H21 119.2 . . ?
C4 N1 C5 113.2(2) . . ?
C4 N1 H22 107(3) . . ?
C5 N1 H22 107(2) . . ?
C1 O1 H1 114(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 59.7(4) . . . . ?
C1 C2 C3 C4 -166.2(3) . . . . ?
C2 C3 C4 N1 175.8(3) . . . . ?
N1 C5 C6 C7 175.7(3) . . . . ?
C5 C6 C7 C17 176.1(3) . . . . ?
C5 C6 C7 C8 -4.2(5) . . . . ?
C17 C7 C8 C9 -1.5(5) . . . . ?
C6 C7 C8 C9 178.8(3) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C16 0.8(5) . . . . ?
C8 C9 C10 C11 -177.6(3) . . . . ?
C9 C10 C11 C19 -146.3(3) . . . . ?
C16 C10 C11 C19 35.3(5) . . . . ?
C9 C10 C11 C12 33.9(5) . . . . ?
C16 C10 C11 C12 -144.5(3) . . . . ?
C19 C11 C12 C13 -0.4(5) . . . . ?
C10 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 C14 1.1(5) . . . . ?
C12 C13 C14 C18 -1.4(5) . . . . ?
C12 C13 C14 C15 177.7(3) . . . . ?
C13 C14 C15 N2 -136(13) . . . . ?
C18 C14 C15 N2 44(13) . . . . ?
C9 C10 C16 C17 -0.8(5) . . . . ?
C11 C10 C16 C17 177.7(3) . . . . ?
C10 C16 C17 C7 -0.3(5) . . . . ?
C8 C7 C17 C16 1.5(5) . . . . ?
C6 C7 C17 C16 -178.8(3) . . . . ?
C13 C14 C18 C19 1.0(5) . . . . ?
C15 C14 C18 C19 -178.1(3) . . . . ?
C14 C18 C19 C11 -0.3(5) . . . . ?
C12 C11 C19 C18 0.0(5) . . . . ?
C10 C11 C19 C18 -179.8(3) . . . . ?
C3 C4 N1 C5 -178.3(3) . . . . ?
C6 C5 N1 C4 178.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.103
