# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_pnma_sq
_database_code_depnum_ccdc_archive 'CCDC 2049603'
loop_
_audit_author_name
_audit_author_address
'Miao Fang'
;UESTC
China
;
_audit_update_record             
;
2020-12-11 deposited with the CCDC.	2023-02-01 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            'C33 H33 N3 O'
_chemical_formula_weight         487.62

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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   27.4526(15)
_cell_length_b                   6.8462(4)
_cell_length_c                   18.7535(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3524.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3025
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      66.58
_cell_measurement_temperature    184.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    0.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    0.433
_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  0.5892
_exptl_absorpt_correction_T_max  0.7528

_exptl_special_details           
;
;

_diffrn_ambient_temperature      184.(2)

_diffrn_source                   'Incoatec Ius 3.0'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helios MX multilayer'

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13669
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.220
_diffrn_reflns_theta_max         66.672
_diffrn_reflns_theta_full        66.672
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3380
_reflns_number_gt                2234
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    ?
_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)+(0.0934P)²+0.1813P] 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         3380
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1828
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_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 0.37627(10) 0.250000 0.42735(17) 0.0602(7) Uani 1 2 d S T P . .
H1 H 0.373401 0.250000 0.477830 0.072 Uiso 1 2 calc R U P . .
C2 C 0.33461(12) 0.250000 0.38528(19) 0.0714(8) Uani 1 2 d S T P . .
H2 H 0.303421 0.250000 0.407242 0.086 Uiso 1 2 calc R U P . .
C3 C 0.33809(13) 0.250000 0.31271(19) 0.0731(9) Uani 1 2 d S T P . .
H3 H 0.309419 0.250000 0.284345 0.088 Uiso 1 2 calc R U P . .
C4 C 0.38313(13) 0.250000 0.28068(18) 0.0702(8) Uani 1 2 d S T P . .
H4 H 0.385552 0.250000 0.230144 0.084 Uiso 1 2 calc R U P . .
C5 C 0.42508(11) 0.250000 0.32203(15) 0.0596(7) Uani 1 2 d S T P . .
H5 H 0.456080 0.250000 0.299517 0.072 Uiso 1 2 calc R U P . .
C6 C 0.42218(9) 0.250000 0.39589(14) 0.0501(6) Uani 1 2 d S T P . .
C7 C 0.46659(9) 0.250000 0.44022(13) 0.0466(6) Uani 1 2 d S T P . .
C8 C 0.50170(9) 0.250000 0.55153(13) 0.0442(5) Uani 1 2 d S T P . .
C9 C 0.54934(9) 0.250000 0.51997(12) 0.0409(5) Uani 1 2 d S T P . .
C10 C 0.59082(9) 0.250000 0.56012(12) 0.0447(5) Uani 1 2 d S T P . .
H10 H 0.621599 0.250000 0.536983 0.054 Uiso 1 2 calc R U P . .
C11 C 0.58887(9) 0.250000 0.63535(13) 0.0458(6) Uani 1 2 d S T P . .
C12 C 0.54125(10) 0.250000 0.66659(13) 0.0512(6) Uani 1 2 d S T P . .
H12 H 0.538623 0.250000 0.717105 0.061 Uiso 1 2 calc R U P . .
C13 C 0.50003(10) 0.250000 0.62764(13) 0.0533(6) Uani 1 2 d S T P . .
H13 H 0.469378 0.250000 0.651148 0.064 Uiso 1 2 calc R U P . .
C14 C 0.63195(9) 0.250000 0.67769(13) 0.0468(6) Uani 1 2 d S T P . .
C15 C 0.63069(10) 0.250000 0.75378(13) 0.0522(6) Uani 1 2 d S T P . .
H15 H 0.599808 0.250000 0.776650 0.063 Uiso 1 2 calc R U P . .
C16 C 0.67118(11) 0.250000 0.79518(14) 0.0561(7) Uani 1 2 d S T P . .
C17 C 0.71931(10) 0.250000 0.76058(15) 0.0574(7) Uani 1 2 d S T P . .
C18 C 0.72137(10) 0.250000 0.68202(14) 0.0512(6) Uani 1 2 d S T P . .
C19 C 0.67890(10) 0.250000 0.64529(13) 0.0506(6) Uani 1 2 d S T P . .
H19 H 0.680503 0.250000 0.594689 0.061 Uiso 1 2 calc R U P . .
C20 C 0.66816(13) 0.250000 0.87702(15) 0.0766(9) Uani 1 2 d S T P . .
C21 C 0.61477(15) 0.250000 0.90226(17) 0.1061(15) Uani 1 2 d S T P . .
H21A H 0.598240 0.366611 0.884007 0.159 Uiso 0.5 1 calc R U P . .
H21B H 0.598311 0.132858 0.884327 0.159 Uiso 0.5 1 calc R U P . .
H21C H 0.613788 0.250531 0.954494 0.159 Uiso 1 2 calc R U P . .
C22 C 0.69283(11) 0.4338(5) 0.90643(14) 0.1083(11) Uani 1 1 d . . . . .
H22A H 0.676654 0.549922 0.887151 0.162 Uiso 1 1 calc R U . . .
H22B H 0.690402 0.434471 0.958570 0.162 Uiso 1 1 calc R U . . .
H22C H 0.727214 0.434467 0.892402 0.162 Uiso 1 1 calc R U . . .
C23 C 0.77095(10) 0.250000 0.64385(15) 0.0607(7) Uani 1 2 d S T P . .
C24 C 0.76479(12) 0.250000 0.56279(16) 0.0760(9) Uani 1 2 d S T P . .
H24A H 0.746505 0.366311 0.548241 0.114 Uiso 0.5 1 calc R U P . .
H24B H 0.796919 0.251126 0.540027 0.114 Uiso 1 2 calc R U P . .
H24C H 0.746988 0.132564 0.548162 0.114 Uiso 0.5 1 calc R U P . .
C25 C 0.79964(9) 0.4341(4) 0.66357(15) 0.0874(8) Uani 1 1 d . . . . .
H25A H 0.804279 0.438884 0.715356 0.131 Uiso 1 1 calc R U . . .
H25B H 0.831466 0.431389 0.639919 0.131 Uiso 1 1 calc R U . . .
H25C H 0.781535 0.549949 0.648054 0.131 Uiso 1 1 calc R U . . .
C26 C 0.59492(9) 0.250000 0.40783(12) 0.0495(6) Uani 1 2 d S T P . .
C27 C 0.61725(8) 0.4252(3) 0.39215(10) 0.0616(5) Uani 1 1 d . . . . .
H27 H 0.601913 0.545229 0.404034 0.074 Uiso 1 1 calc R U . . .
C28 C 0.66221(8) 0.4241(4) 0.35894(12) 0.0740(6) Uani 1 1 d . . . . .
H28 H 0.677813 0.543884 0.347435 0.089 Uiso 1 1 calc R U . . .
C29 C 0.68427(12) 0.250000 0.34261(18) 0.0765(9) Uani 1 2 d S T P . .
H29 H 0.715151 0.250002 0.319756 0.092 Uiso 1 2 calc R U P . .
N1 N 0.46111(8) 0.250000 0.51346(11) 0.0484(5) Uani 1 2 d S T P . .
N2 N 0.54947(7) 0.250000 0.44587(10) 0.0465(5) Uani 1 2 d S T P . .
N3 N 0.50860(7) 0.250000 0.40609(10) 0.0475(5) Uani 1 2 d S T P . .
O1 O 0.75764(8) 0.250000 0.79630(11) 0.0768(6) Uani 1 2 d S T P . .


_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 1.389(4) . ?
C1 C6 1.392(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.364(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.476(3) . ?
C7 N3 1.319(3) . ?
C7 N1 1.382(3) . ?
C8 N1 1.323(3) . ?
C8 C13 1.428(4) . ?
C8 C9 1.436(3) . ?
C9 C10 1.365(3) . ?
C9 N2 1.390(3) . ?
C10 C11 1.412(3) . ?
C10 H10 0.9500 . ?
C11 C14 1.424(3) . ?
C11 C12 1.433(4) . ?
C12 C13 1.347(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.425(4) . ?
C14 C15 1.427(4) . ?
C15 C16 1.356(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.472(4) . ?
C16 C20 1.537(4) . ?
C17 O1 1.247(3) . ?
C17 C18 1.475(4) . ?
C18 C19 1.354(4) . ?
C18 C23 1.538(4) . ?
C19 H19 0.9500 . ?
C20 C22 1.531(3) 7_565 ?
C20 C22 1.532(3) . ?
C20 C21 1.540(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21A 0.9799 7_565 ?
C21 H21B 0.9800 7_565 ?
C21 H21C 0.9800 7_565 ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.530(4) . ?
C23 C25 1.532(3) 7_565 ?
C23 C25 1.532(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 H24A 0.9800 7_565 ?
C24 H24B 0.9800 7_565 ?
C24 H24C 0.9800 7_565 ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.378(2) 7_565 ?
C26 C27 1.378(2) . ?
C26 N2 1.437(3) . ?
C27 C28 1.383(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.372(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
N2 N3 1.347(3) . ?

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 C6 120.3(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 121.0(2) . . ?
C1 C6 C7 120.6(2) . . ?
N3 C7 N1 125.3(2) . . ?
N3 C7 C6 116.7(2) . . ?
N1 C7 C6 118.1(2) . . ?
N1 C8 C13 120.8(2) . . ?
N1 C8 C9 123.0(2) . . ?
C13 C8 C9 116.2(2) . . ?
C10 C9 N2 123.3(2) . . ?
C10 C9 C8 122.2(2) . . ?
N2 C9 C8 114.5(2) . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C14 121.7(2) . . ?
C10 C11 C12 116.3(2) . . ?
C14 C11 C12 122.0(2) . . ?
C13 C12 C11 123.0(2) . . ?
C13 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C12 C13 C8 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C11 C14 C19 120.9(2) . . ?
C11 C14 C15 122.5(2) . . ?
C19 C14 C15 116.6(2) . . ?
C16 C15 C14 123.5(3) . . ?
C16 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 C20 121.8(3) . . ?
C17 C16 C20 119.2(2) . . ?
O1 C17 C16 121.4(3) . . ?
O1 C17 C18 120.3(3) . . ?
C16 C17 C18 118.4(2) . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 C23 121.7(2) . . ?
C17 C18 C23 119.9(2) . . ?
C18 C19 C14 124.2(2) . . ?
C18 C19 H19 117.9 . . ?
C14 C19 H19 117.9 . . ?
C22 C20 C22 110.5(3) 7_565 . ?
C22 C20 C16 109.62(19) 7_565 . ?
C22 C20 C16 109.62(19) . . ?
C22 C20 C21 108.1(2) 7_565 . ?
C22 C20 C21 108.1(2) . . ?
C16 C20 C21 111.0(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C21 H21A 109.47(8) . 7_565 ?
H21A C21 H21A 109.1 . 7_565 ?
H21B C21 H21A 0.4 . 7_565 ?
H21C C21 H21A 109.8 . 7_565 ?
C20 C21 H21B 109.47(8) . 7_565 ?
H21A C21 H21B 0.4 . 7_565 ?
H21B C21 H21B 109.8 . 7_565 ?
H21C C21 H21B 109.1 . 7_565 ?
H21A C21 H21B 109.5 7_565 7_565 ?
C20 C21 H21C 109.47(16) . 7_565 ?
H21A C21 H21C 109.8 . 7_565 ?
H21B C21 H21C 109.1 . 7_565 ?
H21C C21 H21C 0.4 . 7_565 ?
H21A C21 H21C 109.5 7_565 7_565 ?
H21B C21 H21C 109.5 7_565 7_565 ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C25 107.26(18) . 7_565 ?
C24 C23 C25 107.27(18) . . ?
C25 C23 C25 110.8(3) 7_565 . ?
C24 C23 C18 111.4(2) . . ?
C25 C23 C18 110.05(17) 7_565 . ?
C25 C23 C18 110.04(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C24 H24A 109.47(8) . 7_565 ?
H24A C24 H24A 108.7 . 7_565 ?
H24B C24 H24A 110.3 . 7_565 ?
H24C C24 H24A 0.9 . 7_565 ?
C23 C24 H24B 109.47(16) . 7_565 ?
H24A C24 H24B 110.2 . 7_565 ?
H24B C24 H24B 0.9 . 7_565 ?
H24C C24 H24B 108.7 . 7_565 ?
H24A C24 H24B 109.5 7_565 7_565 ?
C23 C24 H24C 109.47(8) . 7_565 ?
H24A C24 H24C 0.9 . 7_565 ?
H24B C24 H24C 108.7 . 7_565 ?
H24C C24 H24C 110.3 . 7_565 ?
H24A C24 H24C 109.5 7_565 7_565 ?
H24B C24 H24C 109.5 7_565 7_565 ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C27 120.9(3) 7_565 . ?
C27 C26 N2 119.46(12) 7_565 . ?
C27 C26 N2 119.46(12) . . ?
C26 C27 C28 119.2(2) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C29 C28 C27 120.0(2) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C28 120.7(3) 7_565 . ?
C28 C29 H29 119.7 7_565 . ?
C28 C29 H29 119.7 . . ?
C8 N1 C7 116.4(2) . . ?
N3 N2 C9 123.5(2) . . ?
N3 N2 C26 116.62(18) . . ?
C9 N2 C26 119.90(19) . . ?
C7 N3 N2 117.35(19) . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034




####################################################################### 
# 
# 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_chengdu_3N_0m
_database_code_depnum_ccdc_archive 'CCDC 2049604'
loop_
_audit_author_name
_audit_author_address
'Miao Fang'
;UESTC
China
;
_audit_update_record             
;
2020-12-11 deposited with the CCDC.	2023-02-01 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            'C33 H33 N3 O'
_chemical_formula_weight         487.62

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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.527(3)
_cell_length_b                   10.1852(18)
_cell_length_c                   18.020(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.352(7)
_cell_angle_gamma                90
_cell_volume                     2704.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    184(2)
_cell_measurement_reflns_used    1268
_cell_measurement_theta_min      21.29
_cell_measurement_theta_max      72.28

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    0.564
_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  0.80
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      184(2)

_diffrn_source                   'Incoatec Ius 3.0'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helios MX multilayer'

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16365
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         66.524
_diffrn_reflns_theta_full        66.524
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4757
_reflns_number_gt                3530
_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    ?
_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)+(0.0429P)²+0.7931P] 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         4757
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
N1 N 0.57245(11) 0.41688(15) 0.43576(9) 0.0299(4) Uani 1 1 d . . . . .
N2 N 0.43256(10) 0.27924(15) 0.45981(9) 0.0285(4) Uani 1 1 d . . . . .
N3 N 0.41956(10) 0.33510(15) 0.38842(9) 0.0295(4) Uani 1 1 d . . . . .
C1_1 C 0.54644(14) 0.53263(19) 0.28850(11) 0.0350(5) Uani 1 1 d . . . . .
H1_1 H 0.603592 0.540737 0.327956 0.042 Uiso 1 1 calc R U . . .
C2_1 C 0.53230(16) 0.5931(2) 0.21696(12) 0.0413(5) Uani 1 1 d . . . . .
H2_1 H 0.579727 0.642584 0.207654 0.050 Uiso 1 1 calc R U . . .
C3_1 C 0.44968(16) 0.5820(2) 0.15889(12) 0.0431(5) Uani 1 1 d . . . . .
H3_1 H 0.440324 0.623971 0.109916 0.052 Uiso 1 1 calc R U . . .
C4_1 C 0.38032(15) 0.5093(2) 0.17220(12) 0.0406(5) Uani 1 1 d . . . . .
H4_1 H 0.323395 0.501550 0.132406 0.049 Uiso 1 1 calc R U . . .
C5_1 C 0.39450(14) 0.44788(19) 0.24407(11) 0.0352(5) Uani 1 1 d . . . . .
H5_1 H 0.347281 0.397335 0.252990 0.042 Uiso 1 1 calc R U . . .
C6_1 C 0.47765(13) 0.46004(17) 0.30316(11) 0.0290(4) Uani 1 1 d . . . . .
C7_1 C 0.49232(13) 0.39993(18) 0.38129(11) 0.0286(4) Uani 1 1 d . . . . .
C8_1 C 0.58379(12) 0.35870(17) 0.50748(10) 0.0266(4) Uani 1 1 d . . . . .
C9_1 C 0.51108(13) 0.28498(17) 0.51996(10) 0.0264(4) Uani 1 1 d . . . . .
C10_1 C 0.52319(14) 0.22262(19) 0.59226(11) 0.0331(4) Uani 1 1 d . . . . .
H10_1 H 0.475946 0.170786 0.600128 0.040 Uiso 1 1 calc R U . . .
C11_1 C 0.60300(13) 0.23720(19) 0.65065(11) 0.0336(5) Uani 1 1 d . . . . .
H11_1 H 0.610745 0.193470 0.698889 0.040 Uiso 1 1 calc R U . . .
C12_1 C 0.67574(13) 0.31552(18) 0.64256(11) 0.0290(4) Uani 1 1 d . . . . .
C13_1 C 0.66368(13) 0.37150(18) 0.56895(11) 0.0297(4) Uani 1 1 d . . . . .
H13_1 H 0.712197 0.420121 0.560903 0.036 Uiso 1 1 calc R U . . .
C14_1 C 0.75376(13) 0.34280(19) 0.70997(11) 0.0307(4) Uani 1 1 d . . . . .
C15_1 C 0.80532(13) 0.45879(19) 0.71245(11) 0.0319(4) Uani 1 1 d . . . . .
H15_1 H 0.791794 0.511584 0.666748 0.038 Uiso 1 1 calc R U . . .
C16_1 C 0.87356(13) 0.49833(19) 0.77741(11) 0.0307(4) Uani 1 1 d . . . . .
C17_1 C 0.89616(13) 0.41523(19) 0.84706(11) 0.0322(4) Uani 1 1 d . . . . .
C18_1 C 0.84670(13) 0.29253(19) 0.84455(11) 0.0311(4) Uani 1 1 d . . . . .
C19_1 C 0.77789(13) 0.26272(18) 0.77789(11) 0.0308(4) Uani 1 1 d . . . . .
H19_1 H 0.744462 0.184285 0.776972 0.037 Uiso 1 1 calc R U . . .
C20_1 C 0.92359(14) 0.6293(2) 0.77886(11) 0.0346(5) Uani 1 1 d . . . . .
C21_1 C 1.02571(14) 0.6039(2) 0.79486(13) 0.0461(6) Uani 1 1 d . . . . .
H21A_1 H 1.057063 0.687732 0.795861 0.069 Uiso 1 1 calc R U . . .
H21B_1 H 1.034301 0.548106 0.753459 0.069 Uiso 1 1 calc R U . . .
H21C_1 H 1.050683 0.559828 0.845447 0.069 Uiso 1 1 calc R U . . .
C22_1 C 0.90918(16) 0.7197(2) 0.84204(13) 0.0478(6) Uani 1 1 d . . . . .
H22A_1 H 0.941078 0.802847 0.842492 0.072 Uiso 1 1 calc R U . . .
H22B_1 H 0.933056 0.677208 0.893242 0.072 Uiso 1 1 calc R U . . .
H22C_1 H 0.844191 0.736720 0.830745 0.072 Uiso 1 1 calc R U . . .
C23_1 C 0.88765(16) 0.7021(2) 0.70052(13) 0.0464(6) Uani 1 1 d . . . . .
H23A_1 H 0.921549 0.784076 0.703111 0.070 Uiso 1 1 calc R U . . .
H23B_1 H 0.823139 0.722074 0.689871 0.070 Uiso 1 1 calc R U . . .
H23C_1 H 0.895322 0.646721 0.658582 0.070 Uiso 1 1 calc R U . . .
C24_1 C 0.87112(14) 0.20132(19) 0.91626(11) 0.0341(5) Uani 1 1 d . . . . .
C25_1 C 0.85447(16) 0.2714(2) 0.98598(12) 0.0455(6) Uani 1 1 d . . . . .
H25A_1 H 0.868178 0.211408 1.030692 0.068 Uiso 1 1 calc R U . . .
H25B_1 H 0.790830 0.298836 0.971715 0.068 Uiso 1 1 calc R U . . .
H25C_1 H 0.893776 0.348824 1.000005 0.068 Uiso 1 1 calc R U . . .
C26_1 C 0.97127(15) 0.1592(2) 0.93819(13) 0.0457(6) Uani 1 1 d . . . . .
H26A_1 H 0.988775 0.113466 0.988585 0.069 Uiso 1 1 calc R U . . .
H26B_1 H 1.009514 0.237109 0.942102 0.069 Uiso 1 1 calc R U . . .
H26C_1 H 0.979248 0.100351 0.897844 0.069 Uiso 1 1 calc R U . . .
C27_1 C 0.81324(16) 0.0768(2) 0.90112(13) 0.0485(6) Uani 1 1 d . . . . .
H27A_1 H 0.832427 0.020020 0.947351 0.073 Uiso 1 1 calc R U . . .
H27B_1 H 0.820917 0.029970 0.856098 0.073 Uiso 1 1 calc R U . . .
H27C_1 H 0.749271 0.100435 0.890208 0.073 Uiso 1 1 calc R U . . .
C28_1 C 0.35174(13) 0.21726(18) 0.46739(11) 0.0290(4) Uani 1 1 d . . . . .
C29_1 C 0.30194(13) 0.28404(19) 0.50649(11) 0.0334(4) Uani 1 1 d . . . . .
H29_1 H 0.321481 0.367087 0.529698 0.040 Uiso 1 1 calc R U . . .
C30_1 C 0.22265(14) 0.2272(2) 0.51116(13) 0.0399(5) Uani 1 1 d . . . . .
H30_1 H 0.187108 0.271637 0.537627 0.048 Uiso 1 1 calc R U . . .
C31_1 C 0.19522(14) 0.1061(2) 0.47741(13) 0.0408(5) Uani 1 1 d . . . . .
H31_1 H 0.140702 0.067912 0.480654 0.049 Uiso 1 1 calc R U . . .
C32_1 C 0.24618(15) 0.0403(2) 0.43912(13) 0.0420(5) Uani 1 1 d . . . . .
H32_1 H 0.226997 -0.043051 0.416271 0.050 Uiso 1 1 calc R U . . .
C33_1 C 0.32558(14) 0.0961(2) 0.43398(12) 0.0370(5) Uani 1 1 d . . . . .
H33_1 H 0.361357 0.051405 0.407834 0.044 Uiso 1 1 calc R U . . .
O1_1 O 0.95874(10) 0.45161(16) 0.90922(8) 0.0479(4) 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
N1 C7_1 1.331(2) . ?
N1 C8_1 1.382(2) . ?
N2 C9_1 1.354(2) . ?
N2 N3 1.362(2) . ?
N2 C28_1 1.449(2) . ?
N3 C7_1 1.349(2) . ?
C1_1 C2_1 1.382(3) . ?
C1_1 C6_1 1.391(3) . ?
C1_1 H1_1 0.9500 . ?
C2_1 C3_1 1.381(3) . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.388(3) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.392(3) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.397(3) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.486(3) . ?
C8_1 C13_1 1.385(3) . ?
C8_1 C9_1 1.431(2) . ?
C9_1 C10_1 1.408(3) . ?
C10_1 C11_1 1.358(3) . ?
C10_1 H10_1 0.9500 . ?
C11_1 C12_1 1.427(3) . ?
C11_1 H11_1 0.9500 . ?
C12_1 C13_1 1.401(3) . ?
C12_1 C14_1 1.447(3) . ?
C13_1 H13_1 0.9500 . ?
C14_1 C19_1 1.420(3) . ?
C14_1 C15_1 1.420(3) . ?
C15_1 C16_1 1.369(3) . ?
C15_1 H15_1 0.9500 . ?
C16_1 C17_1 1.462(3) . ?
C16_1 C20_1 1.540(3) . ?
C17_1 O1_1 1.285(2) . ?
C17_1 C18_1 1.460(3) . ?
C18_1 C19_1 1.367(3) . ?
C18_1 C24_1 1.539(3) . ?
C19_1 H19_1 0.9500 . ?
C20_1 C22_1 1.534(3) . ?
C20_1 C23_1 1.536(3) . ?
C20_1 C21_1 1.541(3) . ?
C21_1 H21A_1 0.9800 . ?
C21_1 H21B_1 0.9800 . ?
C21_1 H21C_1 0.9800 . ?
C22_1 H22A_1 0.9800 . ?
C22_1 H22B_1 0.9800 . ?
C22_1 H22C_1 0.9800 . ?
C23_1 H23A_1 0.9800 . ?
C23_1 H23B_1 0.9800 . ?
C23_1 H23C_1 0.9800 . ?
C24_1 C27_1 1.529(3) . ?
C24_1 C25_1 1.536(3) . ?
C24_1 C26_1 1.540(3) . ?
C25_1 H25A_1 0.9800 . ?
C25_1 H25B_1 0.9800 . ?
C25_1 H25C_1 0.9800 . ?
C26_1 H26A_1 0.9800 . ?
C26_1 H26B_1 0.9800 . ?
C26_1 H26C_1 0.9800 . ?
C27_1 H27A_1 0.9800 . ?
C27_1 H27B_1 0.9800 . ?
C27_1 H27C_1 0.9800 . ?
C28_1 C33_1 1.377(3) . ?
C28_1 C29_1 1.378(3) . ?
C29_1 C30_1 1.387(3) . ?
C29_1 H29_1 0.9500 . ?
C30_1 C31_1 1.382(3) . ?
C30_1 H30_1 0.9500 . ?
C31_1 C32_1 1.376(3) . ?
C31_1 H31_1 0.9500 . ?
C32_1 C33_1 1.387(3) . ?
C32_1 H32_1 0.9500 . ?
C33_1 H33_1 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
C7_1 N1 C8_1 116.64(16) . . ?
C9_1 N2 N3 124.49(15) . . ?
C9_1 N2 C28_1 122.13(15) . . ?
N3 N2 C28_1 113.31(15) . . ?
C7_1 N3 N2 114.50(15) . . ?
C2_1 C1_1 C6_1 120.5(2) . . ?
C2_1 C1_1 H1_1 119.7 . . ?
C6_1 C1_1 H1_1 119.7 . . ?
C3_1 C2_1 C1_1 120.5(2) . . ?
C3_1 C2_1 H2_1 119.8 . . ?
C1_1 C2_1 H2_1 119.8 . . ?
C2_1 C3_1 C4_1 119.92(19) . . ?
C2_1 C3_1 H3_1 120.0 . . ?
C4_1 C3_1 H3_1 120.0 . . ?
C3_1 C4_1 C5_1 119.7(2) . . ?
C3_1 C4_1 H4_1 120.1 . . ?
C5_1 C4_1 H4_1 120.1 . . ?
C4_1 C5_1 C6_1 120.46(19) . . ?
C4_1 C5_1 H5_1 119.8 . . ?
C6_1 C5_1 H5_1 119.8 . . ?
C1_1 C6_1 C5_1 118.89(18) . . ?
C1_1 C6_1 C7_1 120.09(18) . . ?
C5_1 C6_1 C7_1 121.00(17) . . ?
N1 C7_1 N3 127.55(17) . . ?
N1 C7_1 C6_1 118.30(16) . . ?
N3 C7_1 C6_1 114.13(17) . . ?
N1 C8_1 C13_1 121.74(16) . . ?
N1 C8_1 C9_1 119.83(17) . . ?
C13_1 C8_1 C9_1 118.42(16) . . ?
N2 C9_1 C10_1 123.07(17) . . ?
N2 C9_1 C8_1 116.93(16) . . ?
C10_1 C9_1 C8_1 120.00(17) . . ?
C11_1 C10_1 C9_1 119.42(18) . . ?
C11_1 C10_1 H10_1 120.3 . . ?
C9_1 C10_1 H10_1 120.3 . . ?
C10_1 C11_1 C12_1 122.71(18) . . ?
C10_1 C11_1 H11_1 118.6 . . ?
C12_1 C11_1 H11_1 118.6 . . ?
C13_1 C12_1 C11_1 116.75(17) . . ?
C13_1 C12_1 C14_1 122.93(17) . . ?
C11_1 C12_1 C14_1 120.12(17) . . ?
C8_1 C13_1 C12_1 122.55(17) . . ?
C8_1 C13_1 H13_1 118.7 . . ?
C12_1 C13_1 H13_1 118.7 . . ?
C19_1 C14_1 C15_1 117.24(18) . . ?
C19_1 C14_1 C12_1 122.51(17) . . ?
C15_1 C14_1 C12_1 120.06(17) . . ?
C16_1 C15_1 C14_1 123.28(18) . . ?
C16_1 C15_1 H15_1 118.4 . . ?
C14_1 C15_1 H15_1 118.4 . . ?
C15_1 C16_1 C17_1 118.40(18) . . ?
C15_1 C16_1 C20_1 121.33(17) . . ?
C17_1 C16_1 C20_1 120.23(17) . . ?
O1_1 C17_1 C18_1 121.32(18) . . ?
O1_1 C17_1 C16_1 119.51(18) . . ?
C18_1 C17_1 C16_1 119.16(17) . . ?
C19_1 C18_1 C17_1 118.37(17) . . ?
C19_1 C18_1 C24_1 121.44(18) . . ?
C17_1 C18_1 C24_1 120.17(17) . . ?
C18_1 C19_1 C14_1 123.45(18) . . ?
C18_1 C19_1 H19_1 118.3 . . ?
C14_1 C19_1 H19_1 118.3 . . ?
C22_1 C20_1 C23_1 107.24(18) . . ?
C22_1 C20_1 C16_1 109.98(16) . . ?
C23_1 C20_1 C16_1 111.56(17) . . ?
C22_1 C20_1 C21_1 110.09(18) . . ?
C23_1 C20_1 C21_1 107.92(17) . . ?
C16_1 C20_1 C21_1 109.99(17) . . ?
C20_1 C21_1 H21A_1 109.5 . . ?
C20_1 C21_1 H21B_1 109.5 . . ?
H21A_1 C21_1 H21B_1 109.5 . . ?
C20_1 C21_1 H21C_1 109.5 . . ?
H21A_1 C21_1 H21C_1 109.5 . . ?
H21B_1 C21_1 H21C_1 109.5 . . ?
C20_1 C22_1 H22A_1 109.5 . . ?
C20_1 C22_1 H22B_1 109.5 . . ?
H22A_1 C22_1 H22B_1 109.5 . . ?
C20_1 C22_1 H22C_1 109.5 . . ?
H22A_1 C22_1 H22C_1 109.5 . . ?
H22B_1 C22_1 H22C_1 109.5 . . ?
C20_1 C23_1 H23A_1 109.5 . . ?
C20_1 C23_1 H23B_1 109.5 . . ?
H23A_1 C23_1 H23B_1 109.5 . . ?
C20_1 C23_1 H23C_1 109.5 . . ?
H23A_1 C23_1 H23C_1 109.5 . . ?
H23B_1 C23_1 H23C_1 109.5 . . ?
C27_1 C24_1 C25_1 106.91(17) . . ?
C27_1 C24_1 C18_1 112.06(17) . . ?
C25_1 C24_1 C18_1 110.22(16) . . ?
C27_1 C24_1 C26_1 107.71(18) . . ?
C25_1 C24_1 C26_1 109.63(18) . . ?
C18_1 C24_1 C26_1 110.21(16) . . ?
C24_1 C25_1 H25A_1 109.5 . . ?
C24_1 C25_1 H25B_1 109.5 . . ?
H25A_1 C25_1 H25B_1 109.5 . . ?
C24_1 C25_1 H25C_1 109.5 . . ?
H25A_1 C25_1 H25C_1 109.5 . . ?
H25B_1 C25_1 H25C_1 109.5 . . ?
C24_1 C26_1 H26A_1 109.5 . . ?
C24_1 C26_1 H26B_1 109.5 . . ?
H26A_1 C26_1 H26B_1 109.5 . . ?
C24_1 C26_1 H26C_1 109.5 . . ?
H26A_1 C26_1 H26C_1 109.5 . . ?
H26B_1 C26_1 H26C_1 109.5 . . ?
C24_1 C27_1 H27A_1 109.5 . . ?
C24_1 C27_1 H27B_1 109.5 . . ?
H27A_1 C27_1 H27B_1 109.5 . . ?
C24_1 C27_1 H27C_1 109.5 . . ?
H27A_1 C27_1 H27C_1 109.5 . . ?
H27B_1 C27_1 H27C_1 109.5 . . ?
C33_1 C28_1 C29_1 122.00(18) . . ?
C33_1 C28_1 N2 119.62(17) . . ?
C29_1 C28_1 N2 118.36(17) . . ?
C28_1 C29_1 C30_1 118.47(19) . . ?
C28_1 C29_1 H29_1 120.8 . . ?
C30_1 C29_1 H29_1 120.8 . . ?
C31_1 C30_1 C29_1 120.16(19) . . ?
C31_1 C30_1 H30_1 119.9 . . ?
C29_1 C30_1 H30_1 119.9 . . ?
C32_1 C31_1 C30_1 120.58(19) . . ?
C32_1 C31_1 H31_1 119.7 . . ?
C30_1 C31_1 H31_1 119.7 . . ?
C31_1 C32_1 C33_1 119.9(2) . . ?
C31_1 C32_1 H32_1 120.1 . . ?
C33_1 C32_1 H32_1 120.1 . . ?
C28_1 C33_1 C32_1 118.94(19) . . ?
C28_1 C33_1 H33_1 120.5 . . ?
C32_1 C33_1 H33_1 120.5 . . ?

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
C9_1 N2 N3 C7_1 -0.5(2) . . . . ?
C28_1 N2 N3 C7_1 176.42(15) . . . . ?
C6_1 C1_1 C2_1 C3_1 -0.2(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 -0.2(3) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.1(3) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.7(3) . . . . ?
C2_1 C1_1 C6_1 C5_1 0.8(3) . . . . ?
C2_1 C1_1 C6_1 C7_1 -177.56(18) . . . . ?
C4_1 C5_1 C6_1 C1_1 -1.1(3) . . . . ?
C4_1 C5_1 C6_1 C7_1 177.27(18) . . . . ?
C8_1 N1 C7_1 N3 1.9(3) . . . . ?
C8_1 N1 C7_1 C6_1 -179.52(15) . . . . ?
N2 N3 C7_1 N1 -1.6(3) . . . . ?
N2 N3 C7_1 C6_1 179.76(15) . . . . ?
C1_1 C6_1 C7_1 N1 -0.4(3) . . . . ?
C5_1 C6_1 C7_1 N1 -178.76(17) . . . . ?
C1_1 C6_1 C7_1 N3 178.37(17) . . . . ?
C5_1 C6_1 C7_1 N3 0.0(2) . . . . ?
C7_1 N1 C8_1 C13_1 -178.90(17) . . . . ?
C7_1 N1 C8_1 C9_1 -0.1(2) . . . . ?
N3 N2 C9_1 C10_1 -177.93(17) . . . . ?
C28_1 N2 C9_1 C10_1 5.4(3) . . . . ?
N3 N2 C9_1 C8_1 2.1(3) . . . . ?
C28_1 N2 C9_1 C8_1 -174.65(16) . . . . ?
N1 C8_1 C9_1 N2 -1.7(2) . . . . ?
C13_1 C8_1 C9_1 N2 177.15(16) . . . . ?
N1 C8_1 C9_1 C10_1 178.30(17) . . . . ?
C13_1 C8_1 C9_1 C10_1 -2.9(3) . . . . ?
N2 C9_1 C10_1 C11_1 -177.56(18) . . . . ?
C8_1 C9_1 C10_1 C11_1 2.4(3) . . . . ?
C9_1 C10_1 C11_1 C12_1 1.0(3) . . . . ?
C10_1 C11_1 C12_1 C13_1 -3.9(3) . . . . ?
C10_1 C11_1 C12_1 C14_1 171.05(18) . . . . ?
N1 C8_1 C13_1 C12_1 178.63(17) . . . . ?
C9_1 C8_1 C13_1 C12_1 -0.2(3) . . . . ?
C11_1 C12_1 C13_1 C8_1 3.4(3) . . . . ?
C14_1 C12_1 C13_1 C8_1 -171.38(17) . . . . ?
C13_1 C12_1 C14_1 C19_1 -163.39(18) . . . . ?
C11_1 C12_1 C14_1 C19_1 22.0(3) . . . . ?
C13_1 C12_1 C14_1 C15_1 21.7(3) . . . . ?
C11_1 C12_1 C14_1 C15_1 -152.99(18) . . . . ?
C19_1 C14_1 C15_1 C16_1 -2.6(3) . . . . ?
C12_1 C14_1 C15_1 C16_1 172.57(18) . . . . ?
C14_1 C15_1 C16_1 C17_1 1.7(3) . . . . ?
C14_1 C15_1 C16_1 C20_1 -176.16(17) . . . . ?
C15_1 C16_1 C17_1 O1_1 -178.64(18) . . . . ?
C20_1 C16_1 C17_1 O1_1 -0.7(3) . . . . ?
C15_1 C16_1 C17_1 C18_1 1.1(3) . . . . ?
C20_1 C16_1 C17_1 C18_1 179.02(17) . . . . ?
O1_1 C17_1 C18_1 C19_1 176.81(18) . . . . ?
C16_1 C17_1 C18_1 C19_1 -2.9(3) . . . . ?
O1_1 C17_1 C18_1 C24_1 -2.1(3) . . . . ?
C16_1 C17_1 C18_1 C24_1 178.17(17) . . . . ?
C17_1 C18_1 C19_1 C14_1 2.1(3) . . . . ?
C24_1 C18_1 C19_1 C14_1 -179.07(17) . . . . ?
C15_1 C14_1 C19_1 C18_1 0.7(3) . . . . ?
C12_1 C14_1 C19_1 C18_1 -174.43(18) . . . . ?
C15_1 C16_1 C20_1 C22_1 118.2(2) . . . . ?
C17_1 C16_1 C20_1 C22_1 -59.7(2) . . . . ?
C15_1 C16_1 C20_1 C23_1 -0.7(3) . . . . ?
C17_1 C16_1 C20_1 C23_1 -178.54(18) . . . . ?
C15_1 C16_1 C20_1 C21_1 -120.4(2) . . . . ?
C17_1 C16_1 C20_1 C21_1 61.7(2) . . . . ?
C19_1 C18_1 C24_1 C27_1 2.6(3) . . . . ?
C17_1 C18_1 C24_1 C27_1 -178.57(18) . . . . ?
C19_1 C18_1 C24_1 C25_1 -116.4(2) . . . . ?
C17_1 C18_1 C24_1 C25_1 62.5(2) . . . . ?
C19_1 C18_1 C24_1 C26_1 122.5(2) . . . . ?
C17_1 C18_1 C24_1 C26_1 -58.6(2) . . . . ?
C9_1 N2 C28_1 C33_1 -105.2(2) . . . . ?
N3 N2 C28_1 C33_1 77.7(2) . . . . ?
C9_1 N2 C28_1 C29_1 76.5(2) . . . . ?
N3 N2 C28_1 C29_1 -100.6(2) . . . . ?
C33_1 C28_1 C29_1 C30_1 -0.8(3) . . . . ?
N2 C28_1 C29_1 C30_1 177.51(17) . . . . ?
C28_1 C29_1 C30_1 C31_1 0.3(3) . . . . ?
C29_1 C30_1 C31_1 C32_1 0.2(3) . . . . ?
C30_1 C31_1 C32_1 C33_1 -0.3(3) . . . . ?
C29_1 C28_1 C33_1 C32_1 0.7(3) . . . . ?
N2 C28_1 C33_1 C32_1 -177.52(18) . . . . ?
C31_1 C32_1 C33_1 C28_1 -0.2(3) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041



