# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_dzt_zztl1
_database_code_depnum_ccdc_archive 'CCDC 2355054'
loop_
_audit_author_name
_audit_author_address
'tian le'
;Yunnan University
China
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         256.30

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   5.4192(5)
_cell_length_b                   15.6201(14)
_cell_length_c                   16.4094(14)
_cell_angle_alpha                70.796(4)
_cell_angle_beta                 87.714(4)
_cell_angle_gamma                83.915(4)
_cell_volume                     1304.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9844
_cell_measurement_theta_min      2.8516
_cell_measurement_theta_max      68.4004
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            28645
_diffrn_reflns_av_R_equivalents  0.1328
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         68.84
_diffrn_reflns_theta_full        68.84
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             4795
_reflns_number_gt                3367
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0849
_refine_ls_wR_factor_gt          0.2330
_refine_ls_wR_factor_ref         0.2697
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_number_reflns         4795
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1599P)²+0.5460P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.384
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0032(12)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5575(4) 0.70649(14) 0.20343(13) 0.0372(5) Uani d . . . 1 . .
O O2 0.2219(5) 0.55344(16) 0.52419(14) 0.0449(6) Uani d . . . 1 . .
O O3 1.2688(4) 0.95815(13) -0.04608(13) 0.0356(5) Uani d . . . 1 . .
O O4 0.9959(4) 0.79562(15) 0.28170(13) 0.0392(5) Uani d . . . 1 . .
N N1 0.5834(5) 0.68492(17) 0.34587(15) 0.0345(6) Uani d . . . 1 . .
H H29 0.712311 0.716886 0.335094 0.041 Uiso calc U . R 1 . .
N N2 0.2182(5) 0.56738(17) 0.38316(15) 0.0346(6) Uani d . . . 1 . .
H H30 0.100228 0.530498 0.393832 0.041 Uiso calc U . R 1 . .
N N3 1.3233(5) 0.93183(17) 0.09617(15) 0.0356(6) Uani d . . . 1 . .
H H31 1.455541 0.961997 0.083507 0.043 Uiso calc U . R 1 . .
N N4 0.9677(5) 0.81176(16) 0.14025(15) 0.0326(6) Uani d . . . 1 . .
H H32 0.861169 0.770424 0.153404 0.039 Uiso calc U . R 1 . .
C C1 -0.1633(7) 0.3508(2) 0.2383(2) 0.0422(8) Uani d . . . 1 . .
H H1 -0.250978 0.300528 0.24053 0.051 Uiso calc U . R 1 . .
C C2 0.0424(6) 0.3698(2) 0.1852(2) 0.0391(7) Uani d . . . 1 . .
H H10 0.092976 0.333811 0.149581 0.047 Uiso calc U . R 1 . .
C C3 0.1755(6) 0.4421(2) 0.18390(19) 0.0363(7) Uani d . . . 1 . .
H H7 0.317361 0.45475 0.147617 0.044 Uiso calc U . R 1 . .
C C4 0.1021(6) 0.49625(19) 0.23565(18) 0.0316(6) Uani d . . . 1 . .
C C5 0.2523(6) 0.5692(2) 0.23381(18) 0.0336(7) Uani d . . . 1 . .
H H6 0.323669 0.599037 0.179329 0.04 Uiso calc U . R 1 . .
C C6 0.3043(5) 0.60034(18) 0.29739(17) 0.0299(6) Uani d . . . 1 . .
C C7 0.4892(6) 0.66907(19) 0.27863(18) 0.0321(6) Uani d . . . 1 . .
C C8 0.4959(6) 0.6550(2) 0.43509(18) 0.0343(7) Uani d . . . 1 . .
H H11 0.641533 0.623794 0.472651 0.041 Uiso calc U . R 1 . .
C C9 0.3953(6) 0.7358(2) 0.4612(2) 0.0394(7) Uani d . . . 1 . .
H H12 0.246188 0.768605 0.434264 0.047 Uiso calc U . R 1 . .
C C10 0.4947(7) 0.7659(2) 0.5183(2) 0.0435(8) Uani d . . . 1 . .
C C11 0.7313(8) 0.7269(3) 0.5660(2) 0.0532(9) Uani d . . . 1 . .
H H14 0.796642 0.672061 0.552612 0.08 Uiso calc U . R 1 . .
H H2 0.699831 0.711001 0.628213 0.08 Uiso calc U . R 1 . .
H H13 0.852669 0.771924 0.548605 0.08 Uiso calc U . R 1 . .
C C12 0.3681(9) 0.8471(3) 0.5387(3) 0.0612(11) Uani d . . . 1 . .
H H5 0.218815 0.870529 0.503276 0.092 Uiso calc U . R 1 . .
H H4 0.481532 0.894785 0.526101 0.092 Uiso calc U . R 1 . .
H H3 0.321597 0.82892 0.599871 0.092 Uiso calc U . R 1 . .
C C13 0.3024(6) 0.5879(2) 0.45070(18) 0.0339(7) Uani d . . . 1 . .
C C14 -0.2413(6) 0.4045(2) 0.28812(19) 0.0395(7) Uani d . . . 1 . .
H H9 -0.384778 0.391879 0.323562 0.047 Uiso calc U . R 1 . .
C C15 -0.1119(6) 0.4766(2) 0.28675(18) 0.0326(6) Uani d . . . 1 . .
H H8 -0.168754 0.513427 0.320957 0.039 Uiso calc U . R 1 . .
C C16 0.4721(6) 0.6235(2) -0.0088(2) 0.0403(7) Uani d . . . 1 . .
H H15 0.370346 0.577611 -0.008859 0.048 Uiso calc U . R 1 . .
C C17 0.4205(6) 0.7118(2) -0.0637(2) 0.0392(7) Uani d . . . 1 . .
H H24 0.281803 0.726576 -0.101109 0.047 Uiso calc U . R 1 . .
C C18 0.5697(6) 0.7789(2) -0.06450(19) 0.0358(7) Uani d . . . 1 . .
H H25 0.536449 0.838773 -0.104059 0.043 Uiso calc U . R 1 . .
C C19 0.7680(6) 0.7591(2) -0.00767(18) 0.0322(6) Uani d . . . 1 . .
C C20 0.9283(6) 0.8313(2) -0.01177(19) 0.0334(6) Uani d . . . 1 . .
H H21 0.968457 0.868801 -0.068197 0.04 Uiso calc U . R 1 . .
C C21 1.0247(6) 0.85111(19) 0.05279(18) 0.0318(6) Uani d . . . 1 . .
C C22 1.2124(6) 0.91950(19) 0.03041(18) 0.0311(6) Uani d . . . 1 . .
C C23 1.2499(7) 0.9010(2) 0.1864(2) 0.0421(8) Uani d . . . 1 . .
H H26 1.401866 0.870651 0.220753 0.051 Uiso calc U . R 1 . .
C C24 1.1561(7) 0.9778(2) 0.2151(2) 0.0485(8) Uani d . . . 1 . .
H H20 0.994597 1.005615 0.196253 0.058 Uiso calc U . R 1 . .
C C25 1.2751(9) 1.0135(3) 0.2656(2) 0.0570(10) Uani d . . . 1 . .
C C26 1.1540(10) 1.0953(3) 0.2824(3) 0.0722(13) Uani d . . . 1 . .
H H28 0.995466 1.114038 0.251775 0.108 Uiso calc U . R 1 . .
H H16 1.261791 1.14474 0.262073 0.108 Uiso calc U . R 1 . .
H H27 1.124182 1.081367 0.344512 0.108 Uiso calc U . R 1 . .
C C27 1.5193(10) 0.9794(3) 0.3053(3) 0.0780(14) Uani d . . . 1 . .
H H19 1.585976 0.926048 0.289621 0.117 Uiso calc U . R 1 . .
H H17 1.502898 0.962077 0.368235 0.117 Uiso calc U . R 1 . .
H H18 1.632233 1.027138 0.284696 0.117 Uiso calc U . R 1 . .
C C28 1.0609(6) 0.83135(19) 0.20599(18) 0.0330(6) Uani d . . . 1 . .
C C29 0.6730(6) 0.6023(2) 0.04633(19) 0.0384(7) Uani d . . . 1 . .
H H22 0.710727 0.541633 0.083604 0.046 Uiso calc U . R 1 . .
C C30 0.8200(6) 0.6703(2) 0.04710(18) 0.0356(7) Uani d . . . 1 . .
H H23 0.956637 0.655633 0.085392 0.043 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.239(3) ?
O2 C13 . 1.231(4) ?
O3 C22 . 1.242(3) ?
O4 C28 . 1.237(4) ?
N1 C7 . 1.338(4) ?
N1 C8 . 1.459(4) ?
N1 H29 . 0.88 ?
N2 C13 . 1.358(4) ?
N2 C6 . 1.409(4) ?
N2 H30 . 0.88 ?
N3 C22 . 1.333(4) ?
N3 C23 . 1.451(4) ?
N3 H31 . 0.88 ?
N4 C28 . 1.344(4) ?
N4 C21 . 1.399(4) ?
N4 H32 . 0.88 ?
C1 C14 . 1.377(4) ?
C1 C2 . 1.384(5) ?
C1 H1 . 0.95 ?
C2 C3 . 1.398(4) ?
C2 H10 . 0.95 ?
C3 C4 . 1.403(4) ?
C3 H7 . 0.95 ?
C4 C15 . 1.404(4) ?
C4 C5 . 1.461(4) ?
C5 C6 . 1.338(4) ?
C5 H6 . 0.95 ?
C6 C7 . 1.496(4) ?
C8 C9 . 1.505(4) ?
C8 C13 . 1.516(4) ?
C8 H11 . 1.0 ?
C9 C10 . 1.331(4) ?
C9 H12 . 0.95 ?
C10 C11 . 1.494(5) ?
C10 C12 . 1.506(5) ?
C11 H14 . 0.98 ?
C11 H2 . 0.98 ?
C11 H13 . 0.98 ?
C12 H5 . 0.98 ?
C12 H4 . 0.98 ?
C12 H3 . 0.98 ?
C14 C15 . 1.382(4) ?
C14 H9 . 0.95 ?
C15 H8 . 0.95 ?
C16 C17 . 1.383(5) ?
C16 C29 . 1.384(5) ?
C16 H15 . 0.95 ?
C17 C18 . 1.386(4) ?
C17 H24 . 0.95 ?
C18 C19 . 1.393(4) ?
C18 H25 . 0.95 ?
C19 C30 . 1.389(4) ?
C19 C20 . 1.477(4) ?
C20 C21 . 1.336(4) ?
C20 H21 . 0.95 ?
C21 C22 . 1.501(4) ?
C23 C24 . 1.464(5) ?
C23 C28 . 1.521(4) ?
C23 H26 . 1.0 ?
C24 C25 . 1.356(5) ?
C24 H20 . 0.95 ?
C25 C27 . 1.467(7) ?
C25 C26 . 1.476(6) ?
C26 H28 . 0.98 ?
C26 H16 . 0.98 ?
C26 H27 . 0.98 ?
C27 H19 . 0.98 ?
C27 H17 . 0.98 ?
C27 H18 . 0.98 ?
C29 C30 . 1.396(4) ?
C29 H22 . 0.95 ?
C30 H23 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C8 . . 127.1(3) ?
C7 N1 H29 . . 116.4 ?
C8 N1 H29 . . 116.4 ?
C13 N2 C6 . . 125.3(3) ?
C13 N2 H30 . . 117.3 ?
C6 N2 H30 . . 117.3 ?
C22 N3 C23 . . 127.1(3) ?
C22 N3 H31 . . 116.4 ?
C23 N3 H31 . . 116.4 ?
C28 N4 C21 . . 125.9(3) ?
C28 N4 H32 . . 117.0 ?
C21 N4 H32 . . 117.0 ?
C14 C1 C2 . . 120.2(3) ?
C14 C1 H1 . . 119.9 ?
C2 C1 H1 . . 119.9 ?
C1 C2 C3 . . 119.8(3) ?
C1 C2 H10 . . 120.1 ?
C3 C2 H10 . . 120.1 ?
C2 C3 C4 . . 120.7(3) ?
C2 C3 H7 . . 119.6 ?
C4 C3 H7 . . 119.6 ?
C3 C4 C15 . . 117.8(3) ?
C3 C4 C5 . . 118.5(3) ?
C15 C4 C5 . . 123.8(3) ?
C6 C5 C4 . . 129.7(3) ?
C6 C5 H6 . . 115.2 ?
C4 C5 H6 . . 115.2 ?
C5 C6 N2 . . 125.4(3) ?
C5 C6 C7 . . 117.5(3) ?
N2 C6 C7 . . 116.8(2) ?
O1 C7 N1 . . 122.2(3) ?
O1 C7 C6 . . 120.2(2) ?
N1 C7 C6 . . 117.5(3) ?
N1 C8 C9 . . 110.3(2) ?
N1 C8 C13 . . 112.8(2) ?
C9 C8 C13 . . 110.2(3) ?
N1 C8 H11 . . 107.8 ?
C9 C8 H11 . . 107.8 ?
C13 C8 H11 . . 107.8 ?
C10 C9 C8 . . 126.5(3) ?
C10 C9 H12 . . 116.8 ?
C8 C9 H12 . . 116.8 ?
C9 C10 C11 . . 125.9(3) ?
C9 C10 C12 . . 120.0(3) ?
C11 C10 C12 . . 114.1(3) ?
C10 C11 H14 . . 109.5 ?
C10 C11 H2 . . 109.5 ?
H14 C11 H2 . . 109.5 ?
C10 C11 H13 . . 109.5 ?
H14 C11 H13 . . 109.5 ?
H2 C11 H13 . . 109.5 ?
C10 C12 H5 . . 109.5 ?
C10 C12 H4 . . 109.5 ?
H5 C12 H4 . . 109.5 ?
C10 C12 H3 . . 109.5 ?
H5 C12 H3 . . 109.5 ?
H4 C12 H3 . . 109.5 ?
O2 C13 N2 . . 120.9(3) ?
O2 C13 C8 . . 119.6(3) ?
N2 C13 C8 . . 119.5(3) ?
C1 C14 C15 . . 120.3(3) ?
C1 C14 H9 . . 119.8 ?
C15 C14 H9 . . 119.8 ?
C14 C15 C4 . . 121.1(3) ?
C14 C15 H8 . . 119.5 ?
C4 C15 H8 . . 119.5 ?
C17 C16 C29 . . 119.6(3) ?
C17 C16 H15 . . 120.2 ?
C29 C16 H15 . . 120.2 ?
C16 C17 C18 . . 120.5(3) ?
C16 C17 H24 . . 119.7 ?
C18 C17 H24 . . 119.7 ?
C17 C18 C19 . . 120.4(3) ?
C17 C18 H25 . . 119.8 ?
C19 C18 H25 . . 119.8 ?
C30 C19 C18 . . 118.9(3) ?
C30 C19 C20 . . 121.7(3) ?
C18 C19 C20 . . 119.2(3) ?
C21 C20 C19 . . 129.1(3) ?
C21 C20 H21 . . 115.5 ?
C19 C20 H21 . . 115.5 ?
C20 C21 N4 . . 125.0(3) ?
C20 C21 C22 . . 117.8(3) ?
N4 C21 C22 . . 117.1(2) ?
O3 C22 N3 . . 122.6(3) ?
O3 C22 C21 . . 120.5(3) ?
N3 C22 C21 . . 116.8(3) ?
N3 C23 C24 . . 111.2(3) ?
N3 C23 C28 . . 112.9(2) ?
C24 C23 C28 . . 110.3(3) ?
N3 C23 H26 . . 107.4 ?
C24 C23 H26 . . 107.4 ?
C28 C23 H26 . . 107.4 ?
C25 C24 C23 . . 126.9(4) ?
C25 C24 H20 . . 116.5 ?
C23 C24 H20 . . 116.5 ?
C24 C25 C27 . . 126.2(4) ?
C24 C25 C26 . . 118.3(4) ?
C27 C25 C26 . . 115.5(4) ?
C25 C26 H28 . . 109.5 ?
C25 C26 H16 . . 109.5 ?
H28 C26 H16 . . 109.5 ?
C25 C26 H27 . . 109.5 ?
H28 C26 H27 . . 109.5 ?
H16 C26 H27 . . 109.5 ?
C25 C27 H19 . . 109.5 ?
C25 C27 H17 . . 109.5 ?
H19 C27 H17 . . 109.5 ?
C25 C27 H18 . . 109.5 ?
H19 C27 H18 . . 109.5 ?
H17 C27 H18 . . 109.5 ?
O4 C28 N4 . . 122.3(3) ?
O4 C28 C23 . . 118.9(3) ?
N4 C28 C23 . . 118.8(3) ?
C16 C29 C30 . . 120.0(3) ?
C16 C29 H22 . . 120.0 ?
C30 C29 H22 . . 120.0 ?
C19 C30 C29 . . 120.5(3) ?
C19 C30 H23 . . 119.7 ?
C29 C30 H23 . . 119.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 C1 C2 C3 . . . . 1.9(5) ?
C1 C2 C3 C4 . . . . -0.4(5) ?
C2 C3 C4 C15 . . . . -1.5(4) ?
C2 C3 C4 C5 . . . . 178.2(3) ?
C3 C4 C5 C6 . . . . -144.7(3) ?
C15 C4 C5 C6 . . . . 34.9(5) ?
C4 C5 C6 N2 . . . . -0.5(5) ?
C4 C5 C6 C7 . . . . 172.9(3) ?
C13 N2 C6 C5 . . . . 168.4(3) ?
C13 N2 C6 C7 . . . . -5.1(4) ?
C8 N1 C7 O1 . . . . 171.1(3) ?
C8 N1 C7 C6 . . . . -11.7(4) ?
C5 C6 C7 O1 . . . . 12.0(4) ?
N2 C6 C7 O1 . . . . -174.1(2) ?
C5 C6 C7 N1 . . . . -165.3(3) ?
N2 C6 C7 N1 . . . . 8.7(4) ?
C7 N1 C8 C9 . . . . -114.2(3) ?
C7 N1 C8 C13 . . . . 9.5(4) ?
N1 C8 C9 C10 . . . . -111.7(4) ?
C13 C8 C9 C10 . . . . 123.1(4) ?
C8 C9 C10 C11 . . . . 2.0(6) ?
C8 C9 C10 C12 . . . . -178.8(3) ?
C6 N2 C13 O2 . . . . -177.5(3) ?
C6 N2 C13 C8 . . . . 3.2(4) ?
N1 C8 C13 O2 . . . . 176.3(3) ?
C9 C8 C13 O2 . . . . -60.0(4) ?
N1 C8 C13 N2 . . . . -4.5(4) ?
C9 C8 C13 N2 . . . . 119.2(3) ?
C2 C1 C14 C15 . . . . -1.4(5) ?
C1 C14 C15 C4 . . . . -0.6(5) ?
C3 C4 C15 C14 . . . . 2.0(4) ?
C5 C4 C15 C14 . . . . -177.6(3) ?
C29 C16 C17 C18 . . . . 0.6(4) ?
C16 C17 C18 C19 . . . . -2.5(4) ?
C17 C18 C19 C30 . . . . 2.7(4) ?
C17 C18 C19 C20 . . . . 178.2(3) ?
C30 C19 C20 C21 . . . . -45.7(4) ?
C18 C19 C20 C21 . . . . 139.0(3) ?
C19 C20 C21 N4 . . . . -7.6(5) ?
C19 C20 C21 C22 . . . . 171.2(3) ?
C28 N4 C21 C20 . . . . -179.4(3) ?
C28 N4 C21 C22 . . . . 1.9(4) ?
C23 N3 C22 O3 . . . . 170.5(3) ?
C23 N3 C22 C21 . . . . -13.5(4) ?
C20 C21 C22 O3 . . . . 2.3(4) ?
N4 C21 C22 O3 . . . . -178.9(2) ?
C20 C21 C22 N3 . . . . -173.8(3) ?
N4 C21 C22 N3 . . . . 5.0(4) ?
C22 N3 C23 C24 . . . . -111.0(4) ?
C22 N3 C23 C28 . . . . 13.6(5) ?
N3 C23 C24 C25 . . . . -105.2(4) ?
C28 C23 C24 C25 . . . . 128.7(4) ?
C23 C24 C25 C27 . . . . -3.0(7) ?
C23 C24 C25 C26 . . . . 175.9(4) ?
C21 N4 C28 O4 . . . . 177.8(3) ?
C21 N4 C28 C23 . . . . -1.3(4) ?
N3 C23 C28 O4 . . . . 175.4(3) ?
C24 C23 C28 O4 . . . . -59.5(4) ?
N3 C23 C28 N4 . . . . -5.5(4) ?
C24 C23 C28 N4 . . . . 119.6(3) ?
C17 C16 C29 C30 . . . . 0.9(4) ?
C18 C19 C30 C29 . . . . -1.2(4) ?
C20 C19 C30 C29 . . . . -176.5(3) ?
C16 C29 C30 C19 . . . . -0.6(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H29 O4 . 0.88 2.06 2.921(3) 167.2 ?
N2 H30 O2 2_566 0.88 2.39 3.216(4) 156.3 ?
N3 H31 O3 2_875 0.88 2.00 2.872(3) 173.6 ?
N4 H32 O1 . 0.88 2.02 2.862(3) 159.7 ?



####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2355055'
loop_
_audit_author_name
_audit_author_address
'tian le one'
;Yunnan University
China
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.05500000000000001
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H18 N2 O2'
_chemical_formula_moiety         'C15 H18 N2 O2'
_chemical_formula_weight         258.31
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration unk
_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 Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), C3(H3), C4(H4), C5(H5), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1179(4)
_cell_length_b                   8.0879(6)
_cell_length_c                   27.871(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1379.08(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9822
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      77.40
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5674
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1378 before and 0.0887 after correction.
The Ratio of minimum to maximum transmission is 0.7524.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            21497
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_theta_min         3.171
_diffrn_reflns_theta_max         77.789
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2913
_reflns_number_gt                2783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    1.000
_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       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.0760P)²+0.9526P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2913
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.17(16)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1081 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 -0.1047(3) 0.3496(3) 0.66288(8) 0.0391(6) Uani 1 1 d . . . . .
O2 O 0.6107(3) 0.3104(3) 0.55255(8) 0.0343(5) Uani 1 1 d . . . . .
N1 N 0.0476(4) 0.3116(3) 0.58994(9) 0.0280(5) Uani 1 1 d . . . . .
H1 H -0.078679 0.275787 0.578984 0.034 Uiso 1 1 calc R U . . .
N2 N 0.4610(4) 0.3541(3) 0.62568(9) 0.0286(5) Uani 1 1 d . . . . .
H2 H 0.592716 0.350051 0.638322 0.034 Uiso 1 1 calc R U . . .
C1 C 0.0375(6) 0.7029(4) 0.57831(13) 0.0390(8) Uani 1 1 d . . . . .
H1A H -0.100451 0.649225 0.576678 0.047 Uiso 1 1 calc R U . . .
C2 C 0.0622(7) 0.8430(5) 0.60693(14) 0.0490(9) Uani 1 1 d . . . . .
H2A H -0.058556 0.884655 0.624628 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2635(7) 0.9213(5) 0.60952(14) 0.0488(10) Uani 1 1 d . . . . .
H3 H 0.281174 1.015769 0.629416 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4385(7) 0.8625(5) 0.58326(14) 0.0468(9) Uani 1 1 d . . . . .
H4 H 0.575804 0.917079 0.584699 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4126(6) 0.7234(4) 0.55479(12) 0.0371(7) Uani 1 1 d . . . . .
H5 H 0.533274 0.683358 0.536751 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2127(5) 0.6410(4) 0.55213(10) 0.0305(6) Uani 1 1 d . . . . .
C7 C 0.1927(5) 0.4827(4) 0.52375(11) 0.0319(7) Uani 1 1 d . . . . .
H7A H 0.303730 0.482391 0.497920 0.038 Uiso 1 1 calc R U . . .
H7B H 0.046661 0.478497 0.508485 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2237(4) 0.3275(4) 0.55531(10) 0.0266(6) Uani 1 1 d . . . . .
H8 H 0.217603 0.228790 0.533728 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4472(5) 0.3301(4) 0.57851(11) 0.0268(6) Uani 1 1 d . . . . .
C10 C 0.2815(5) 0.3861(4) 0.65843(11) 0.0323(7) Uani 1 1 d . . . . .
H10 H 0.283186 0.506812 0.666204 0.039 Uiso 1 1 calc R U . . .
C11 C 0.0582(5) 0.3459(4) 0.63659(11) 0.0303(6) Uani 1 1 d . . . . .
C12 C 0.3227(6) 0.2928(5) 0.70437(12) 0.0416(8) Uani 1 1 d . . . . .
H12 H 0.396844 0.190295 0.700869 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2704(6) 0.3334(6) 0.74869(14) 0.0475(9) Uani 1 1 d . . . . .
C14 C 0.1490(8) 0.4879(7) 0.76169(17) 0.0625(12) Uani 1 1 d . . . . .
H14A H 0.151748 0.564752 0.734497 0.094 Uiso 1 1 calc R U . . .
H14B H 0.218653 0.539875 0.789535 0.094 Uiso 1 1 calc R U . . .
H14C H -0.002816 0.460296 0.769526 0.094 Uiso 1 1 calc R U . . .
C15 C 0.3286(8) 0.2216(7) 0.79002(15) 0.0605(12) Uani 1 1 d . . . . .
H15A H 0.403626 0.123174 0.777833 0.091 Uiso 1 1 calc R U . . .
H15B H 0.194937 0.188348 0.806831 0.091 Uiso 1 1 calc R U . . .
H15C H 0.424956 0.280692 0.812267 0.091 Uiso 1 1 calc R U . . .


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 C11 1.237(4) . ?
O2 C9 1.244(3) . ?
N1 H1 0.8800 . ?
N1 C8 1.452(4) . ?
N1 C11 1.331(4) . ?
N2 H2 0.8800 . ?
N2 C9 1.332(4) . ?
N2 C10 1.451(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.394(5) . ?
C1 C6 1.390(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(4) . ?
C6 C7 1.510(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.545(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.513(4) . ?
C10 H10 1.0000 . ?
C10 C11 1.531(4) . ?
C10 C12 1.508(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.318(5) . ?
C13 C14 1.498(6) . ?
C13 C15 1.507(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C8 N1 H1 116.7 . . ?
C11 N1 H1 116.7 . . ?
C11 N1 C8 126.5(3) . . ?
C9 N2 H2 116.6 . . ?
C9 N2 C10 126.8(2) . . ?
C10 N2 H2 116.6 . . ?
C2 C1 H1A 119.7 . . ?
C6 C1 H1A 119.7 . . ?
C6 C1 C2 120.6(4) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 121.2(3) . . ?
C5 C6 C7 120.3(3) . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.4(2) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
N1 C8 C7 111.0(2) . . ?
N1 C8 H8 107.6 . . ?
N1 C8 C9 112.8(2) . . ?
C7 C8 H8 107.6 . . ?
C9 C8 C7 110.1(2) . . ?
C9 C8 H8 107.6 . . ?
O2 C9 N2 122.8(3) . . ?
O2 C9 C8 118.4(2) . . ?
N2 C9 C8 118.8(3) . . ?
N2 C10 H10 107.6 . . ?
N2 C10 C11 112.8(2) . . ?
N2 C10 C12 108.5(3) . . ?
C11 C10 H10 107.6 . . ?
C12 C10 H10 107.6 . . ?
C12 C10 C11 112.4(3) . . ?
O1 C11 N1 123.0(3) . . ?
O1 C11 C10 118.6(3) . . ?
N1 C11 C10 118.4(3) . . ?
C10 C12 H12 115.4 . . ?
C13 C12 C10 129.1(4) . . ?
C13 C12 H12 115.4 . . ?
C12 C13 C14 123.7(4) . . ?
C12 C13 C15 120.6(4) . . ?
C14 C13 C15 115.6(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.88 2.06 2.869(3) 152.9 1_455 yes
N2 H2 O1 0.88 1.97 2.852(3) 176.1 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 O2 166.0(3) . . . . ?
N1 C8 C9 N2 -14.3(4) . . . . ?
N2 C10 C11 O1 171.6(3) . . . . ?
N2 C10 C11 N1 -9.7(4) . . . . ?
N2 C10 C12 C13 147.0(4) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C1 C6 C7 C8 -82.1(4) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C2 C1 C6 C7 175.6(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C4 C5 C6 C7 -175.5(3) . . . . ?
C5 C6 C7 C8 94.2(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C6 C7 C8 N1 66.1(3) . . . . ?
C6 C7 C8 C9 -59.6(3) . . . . ?
C7 C8 C9 O2 -69.3(3) . . . . ?
C7 C8 C9 N2 110.4(3) . . . . ?
C8 N1 C11 O1 170.6(3) . . . . ?
C8 N1 C11 C10 -8.1(5) . . . . ?
C9 N2 C10 C11 15.3(4) . . . . ?
C9 N2 C10 C12 140.5(3) . . . . ?
C10 N2 C9 O2 176.8(3) . . . . ?
C10 N2 C9 C8 -2.9(5) . . . . ?
C10 C12 C13 C14 1.4(7) . . . . ?
C10 C12 C13 C15 -179.7(4) . . . . ?
C11 N1 C8 C7 -103.8(3) . . . . ?
C11 N1 C8 C9 20.3(4) . . . . ?
C11 C10 C12 C13 -87.5(5) . . . . ?
C12 C10 C11 O1 48.5(4) . . . . ?
C12 C10 C11 N1 -132.8(3) . . . . ?

