# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zjf015
_database_code_depnum_ccdc_archive 'CCDC 2231984'
loop_
_audit_author_name
_audit_author_address
'Jianfeng Zheng'
;Southwest Jiaotong University
China
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2024-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H33 N3 O3'
_chemical_formula_sum            'C29 H33 N3 O3'
_chemical_formula_weight         471.58

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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   25.3489(3)
_cell_length_b                   25.3489(3)
_cell_length_c                   27.6292(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     15375.1(5)
_cell_formula_units_Z            18
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9586
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      68.25

_exptl_crystal_description       cube
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.917
_exptl_crystal_F_000             4536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.475
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7606
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20003
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         68.284
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             6042
_reflns_number_gt                4863
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00099(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6042
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.1171
_refine_ls_wR_factor_ref         0.3069
_refine_ls_wR_factor_gt          0.2895
_refine_ls_goodness_of_fit_ref   1.286
_refine_ls_restrained_S_all      1.286
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80228(9) 0.76682(10) 0.53020(7) 0.0183(5) Uani 1 1 d . . . . .
O2 O 0.74769(11) 0.68568(11) 0.47997(8) 0.0259(5) Uani 1 1 d . . . . .
O3 O 0.55777(13) 0.67167(12) 0.65064(10) 0.0323(6) Uani 1 1 d . . . . .
N1 N 0.70250(11) 0.71599(10) 0.53707(8) 0.0123(5) Uani 1 1 d . . . . .
H1N H 0.714(2) 0.743(2) 0.5612(19) 0.034(12) Uiso 1 1 d . . . . .
N2 N 0.54297(10) 0.57706(11) 0.66822(8) 0.0117(5) Uani 1 1 d . . . . .
N3 N 0.45569(11) 0.39824(11) 0.70695(8) 0.0154(5) Uani 1 1 d . . . . .
C1 C 0.86226(14) 0.77593(17) 0.51602(10) 0.0229(7) Uani 1 1 d . . . . .
C2 C 0.8674(2) 0.7217(3) 0.53177(15) 0.0450(11) Uani 1 1 d . . . . .
H2A H 0.859359 0.715045 0.566580 0.067 Uiso 1 1 calc R U . . .
H2B H 0.908560 0.729263 0.524916 0.067 Uiso 1 1 calc R U . . .
H2C H 0.837614 0.685404 0.514045 0.067 Uiso 1 1 calc R U . . .
C3 C 0.87336(16) 0.78834(17) 0.46192(11) 0.0276(7) Uani 1 1 d . . . . .
H3A H 0.840825 0.754472 0.443768 0.041 Uiso 1 1 calc R U . . .
H3B H 0.912700 0.792355 0.453279 0.041 Uiso 1 1 calc R U . . .
H3C H 0.873671 0.826159 0.453920 0.041 Uiso 1 1 calc R U . . .
C4 C 0.90535(16) 0.8331(2) 0.54409(15) 0.0444(11) Uani 1 1 d . . . . .
H4A H 0.899632 0.824560 0.578882 0.067 Uiso 1 1 calc R U . . .
H4B H 0.896681 0.865703 0.536214 0.067 Uiso 1 1 calc R U . . .
H4C H 0.947519 0.845886 0.535276 0.067 Uiso 1 1 calc R U . . .
C5 C 0.75086(13) 0.71945(12) 0.51278(9) 0.0125(5) Uani 1 1 d . . . . .
C11 C 0.64163(12) 0.67331(13) 0.52443(9) 0.0130(5) Uani 1 1 d . . . . .
C12 C 0.60035(13) 0.63373(13) 0.55853(9) 0.0150(6) Uani 1 1 d . . . . .
C13 C 0.54130(15) 0.59154(17) 0.54375(12) 0.0301(8) Uani 1 1 d . . . . .
H13 H 0.513199 0.563918 0.566748 0.036 Uiso 1 1 calc R U . . .
C14 C 0.52291(16) 0.58919(19) 0.49614(13) 0.0359(9) Uani 1 1 d . . . . .
H14 H 0.482420 0.560607 0.486715 0.043 Uiso 1 1 calc R U . . .
C15 C 0.56432(17) 0.62909(18) 0.46230(11) 0.0304(8) Uani 1 1 d . . . . .
H15 H 0.552433 0.627341 0.429462 0.036 Uiso 1 1 calc R U . . .
C16 C 0.62261(14) 0.67114(15) 0.47653(10) 0.0213(6) Uani 1 1 d . . . . .
H16 H 0.650313 0.699077 0.453495 0.026 Uiso 1 1 calc R U . . .
C21 C 0.57141(13) 0.63290(13) 0.64509(9) 0.0150(6) Uani 1 1 d . . . . .
C22 C 0.61926(12) 0.63411(12) 0.61077(9) 0.0123(5) Uani 1 1 d . . . . .
H22 H 0.659602 0.671301 0.616984 0.015 Uiso 1 1 calc R U . . .
C23 C 0.62218(11) 0.57575(12) 0.62458(8) 0.0103(5) Uani 1 1 d . . . . .
H23 H 0.620966 0.553307 0.594447 0.012 Uiso 1 1 calc R U . . .
C24 C 0.56357(11) 0.53873(12) 0.65267(8) 0.0093(5) Uani 1 1 d . . . . .
C25 C 0.53127(12) 0.47855(12) 0.66363(8) 0.0110(5) Uani 1 1 d . . . . .
C26 C 0.48323(12) 0.45733(12) 0.69977(8) 0.0117(5) Uani 1 1 d . . . . .
C27 C 0.48425(13) 0.55429(13) 0.69329(9) 0.0154(6) Uani 1 1 d . . . . .
H27A H 0.450972 0.539960 0.669204 0.019 Uiso 1 1 calc R U . . .
H27B H 0.484674 0.587666 0.712212 0.019 Uiso 1 1 calc R U . . .
C28 C 0.47290(12) 0.50201(12) 0.72705(9) 0.0142(6) Uani 1 1 d . . . . .
H28A H 0.500918 0.517831 0.755077 0.017 Uiso 1 1 calc R U . . .
H28B H 0.430546 0.481945 0.739325 0.017 Uiso 1 1 calc R U . . .
C29 C 0.53171(13) 0.42396(12) 0.64801(9) 0.0132(6) Uani 1 1 d . . . . .
C30 C 0.48416(13) 0.37655(13) 0.67462(9) 0.0144(6) Uani 1 1 d . . . . .
C31 C 0.46784(16) 0.31583(14) 0.66680(12) 0.0251(7) Uani 1 1 d . . . . .
H31 H 0.435544 0.283860 0.684493 0.030 Uiso 1 1 calc R U . . .
C32 C 0.50025(19) 0.30352(16) 0.63237(14) 0.0321(8) Uani 1 1 d . . . . .
H32 H 0.489917 0.262536 0.626431 0.038 Uiso 1 1 calc R U . . .
C33 C 0.54769(17) 0.35045(16) 0.60643(11) 0.0265(7) Uani 1 1 d . . . . .
H33 H 0.569638 0.340875 0.583565 0.032 Uiso 1 1 calc R U . . .
C34 C 0.56357(14) 0.41093(14) 0.61333(10) 0.0182(6) Uani 1 1 d . . . . .
H34 H 0.595252 0.442547 0.594916 0.022 Uiso 1 1 calc R U . . .
C35 C 0.68078(12) 0.59093(13) 0.65435(9) 0.0140(6) Uani 1 1 d . . . . .
C36 C 0.73621(13) 0.62688(16) 0.62117(11) 0.0235(7) Uani 1 1 d . . . . .
H36A H 0.773436 0.635653 0.638536 0.035 Uiso 1 1 calc R U . . .
H36B H 0.738550 0.665210 0.611570 0.035 Uiso 1 1 calc R U . . .
H36C H 0.731959 0.602673 0.592246 0.035 Uiso 1 1 calc R U . . .
C37 C 0.68713(14) 0.62922(15) 0.69939(10) 0.0219(6) Uani 1 1 d . . . . .
H37A H 0.724574 0.638683 0.716735 0.033 Uiso 1 1 calc R U . . .
H37B H 0.651979 0.606210 0.720683 0.033 Uiso 1 1 calc R U . . .
H37C H 0.688881 0.667187 0.689491 0.033 Uiso 1 1 calc R U . . .
C38 C 0.67960(14) 0.53293(15) 0.67072(11) 0.0231(6) Uani 1 1 d . . . . .
H38A H 0.717591 0.543597 0.687702 0.035 Uiso 1 1 calc R U . . .
H38B H 0.675423 0.507825 0.642416 0.035 Uiso 1 1 calc R U . . .
H38C H 0.645020 0.510080 0.692565 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.345(3) . ?
O1 C1 1.472(3) . ?
O2 C5 1.221(4) . ?
O3 C21 1.204(4) . ?
N1 C5 1.362(4) . ?
N1 C11 1.415(3) . ?
N2 C24 1.382(3) . ?
N2 C21 1.382(3) . ?
N2 C27 1.473(3) . ?
N3 C26 1.313(4) . ?
N3 C30 1.420(4) . ?
C1 C2 1.509(5) . ?
C1 C4 1.521(5) . ?
C1 C3 1.524(4) . ?
C11 C12 1.393(4) . ?
C11 C16 1.400(4) . ?
C12 C13 1.396(4) . ?
C12 C22 1.519(3) . ?
C13 C14 1.387(5) . ?
C14 C15 1.392(5) . ?
C15 C16 1.378(5) . ?
C21 C22 1.528(3) . ?
C22 C23 1.565(4) . ?
C23 C24 1.516(3) . ?
C23 C35 1.568(3) . ?
C24 C25 1.356(4) . ?
C25 C26 1.454(3) . ?
C25 C29 1.455(4) . ?
C26 C28 1.489(4) . ?
C27 C28 1.526(3) . ?
C29 C34 1.395(4) . ?
C29 C30 1.410(4) . ?
C30 C31 1.397(4) . ?
C31 C32 1.391(5) . ?
C32 C33 1.394(5) . ?
C33 C34 1.390(4) . ?
C35 C38 1.524(4) . ?
C35 C37 1.536(4) . ?
C35 C36 1.538(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 120.6(2) . . ?
C5 N1 C11 122.0(2) . . ?
C24 N2 C21 112.9(2) . . ?
C24 N2 C27 122.3(2) . . ?
C21 N2 C27 121.8(2) . . ?
C26 N3 C30 105.3(2) . . ?
O1 C1 C2 109.5(3) . . ?
O1 C1 C4 101.9(3) . . ?
C2 C1 C4 111.9(3) . . ?
O1 C1 C3 111.3(2) . . ?
C2 C1 C3 112.3(3) . . ?
C4 C1 C3 109.5(3) . . ?
O2 C5 O1 125.9(3) . . ?
O2 C5 N1 125.4(3) . . ?
O1 C5 N1 108.7(2) . . ?
C12 C11 C16 119.4(3) . . ?
C12 C11 N1 121.5(2) . . ?
C16 C11 N1 119.1(2) . . ?
C11 C12 C13 119.0(3) . . ?
C11 C12 C22 121.1(2) . . ?
C13 C12 C22 119.8(2) . . ?
C14 C13 C12 121.3(3) . . ?
C13 C14 C15 119.4(3) . . ?
C16 C15 C14 119.8(3) . . ?
C15 C16 C11 121.0(3) . . ?
O3 C21 N2 124.2(3) . . ?
O3 C21 C22 127.7(3) . . ?
N2 C21 C22 108.1(2) . . ?
C12 C22 C21 110.2(2) . . ?
C12 C22 C23 112.9(2) . . ?
C21 C22 C23 104.01(19) . . ?
C24 C23 C22 102.4(2) . . ?
C24 C23 C35 113.47(19) . . ?
C22 C23 C35 112.5(2) . . ?
C25 C24 N2 119.6(2) . . ?
C25 C24 C23 131.6(2) . . ?
N2 C24 C23 108.8(2) . . ?
C24 C25 C26 119.5(2) . . ?
C24 C25 C29 135.7(2) . . ?
C26 C25 C29 104.8(2) . . ?
N3 C26 C25 113.3(2) . . ?
N3 C26 C28 126.6(2) . . ?
C25 C26 C28 120.0(2) . . ?
N2 C27 C28 110.0(2) . . ?
C26 C28 C27 108.8(2) . . ?
C34 C29 C30 120.4(3) . . ?
C34 C29 C25 135.2(3) . . ?
C30 C29 C25 104.2(2) . . ?
C31 C30 C29 121.0(3) . . ?
C31 C30 N3 126.6(3) . . ?
C29 C30 N3 112.4(2) . . ?
C32 C31 C30 118.1(3) . . ?
C31 C32 C33 121.0(3) . . ?
C34 C33 C32 121.4(3) . . ?
C33 C34 C29 118.2(3) . . ?
C38 C35 C37 108.3(2) . . ?
C38 C35 C36 108.7(2) . . ?
C37 C35 C36 109.4(2) . . ?
C38 C35 C23 111.1(2) . . ?
C37 C35 C23 111.5(2) . . ?
C36 C35 C23 107.8(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
C5 O1 C1 C2 -61.0(4) . . . . ?
C5 O1 C1 C4 -179.7(3) . . . . ?
C5 O1 C1 C3 63.7(4) . . . . ?
C1 O1 C5 O2 -10.8(4) . . . . ?
C1 O1 C5 N1 170.5(2) . . . . ?
C11 N1 C5 O2 -3.4(4) . . . . ?
C11 N1 C5 O1 175.3(2) . . . . ?
C5 N1 C11 C12 126.6(3) . . . . ?
C5 N1 C11 C16 -53.6(4) . . . . ?
C16 C11 C12 C13 1.8(5) . . . . ?
N1 C11 C12 C13 -178.4(3) . . . . ?
C16 C11 C12 C22 179.4(3) . . . . ?
N1 C11 C12 C22 -0.9(4) . . . . ?
C11 C12 C13 C14 -1.2(6) . . . . ?
C22 C12 C13 C14 -178.8(4) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
C13 C14 C15 C16 -1.2(7) . . . . ?
C14 C15 C16 C11 1.9(6) . . . . ?
C12 C11 C16 C15 -2.2(5) . . . . ?
N1 C11 C16 C15 178.0(3) . . . . ?
C24 N2 C21 O3 174.9(3) . . . . ?
C27 N2 C21 O3 14.3(4) . . . . ?
C24 N2 C21 C22 -2.4(3) . . . . ?
C27 N2 C21 C22 -163.0(2) . . . . ?
C11 C12 C22 C21 134.1(3) . . . . ?
C13 C12 C22 C21 -48.4(4) . . . . ?
C11 C12 C22 C23 -110.1(3) . . . . ?
C13 C12 C22 C23 67.4(4) . . . . ?
O3 C21 C22 C12 -65.9(4) . . . . ?
N2 C21 C22 C12 111.3(3) . . . . ?
O3 C21 C22 C23 172.8(3) . . . . ?
N2 C21 C22 C23 -10.0(3) . . . . ?
C12 C22 C23 C24 -102.2(2) . . . . ?
C21 C22 C23 C24 17.2(2) . . . . ?
C12 C22 C23 C35 135.6(2) . . . . ?
C21 C22 C23 C35 -105.0(2) . . . . ?
C21 N2 C24 C25 -165.3(2) . . . . ?
C27 N2 C24 C25 -4.9(4) . . . . ?
C21 N2 C24 C23 14.5(3) . . . . ?
C27 N2 C24 C23 175.0(2) . . . . ?
C22 C23 C24 C25 160.3(3) . . . . ?
C35 C23 C24 C25 -78.2(3) . . . . ?
C22 C23 C24 N2 -19.5(2) . . . . ?
C35 C23 C24 N2 102.0(2) . . . . ?
N2 C24 C25 C26 -13.0(4) . . . . ?
C23 C24 C25 C26 167.1(2) . . . . ?
N2 C24 C25 C29 167.6(3) . . . . ?
C23 C24 C25 C29 -12.2(5) . . . . ?
C30 N3 C26 C25 -0.8(3) . . . . ?
C30 N3 C26 C28 -175.8(2) . . . . ?
C24 C25 C26 N3 -179.9(2) . . . . ?
C29 C25 C26 N3 -0.4(3) . . . . ?
C24 C25 C26 C28 -4.6(4) . . . . ?
C29 C25 C26 C28 174.9(2) . . . . ?
C24 N2 C27 C28 37.5(3) . . . . ?
C21 N2 C27 C28 -163.7(2) . . . . ?
N3 C26 C28 C27 -149.1(3) . . . . ?
C25 C26 C28 C27 36.2(3) . . . . ?
N2 C27 C28 C26 -49.4(3) . . . . ?
C24 C25 C29 C34 -4.3(6) . . . . ?
C26 C25 C29 C34 176.4(3) . . . . ?
C24 C25 C29 C30 -179.1(3) . . . . ?
C26 C25 C29 C30 1.5(3) . . . . ?
C34 C29 C30 C31 -0.2(4) . . . . ?
C25 C29 C30 C31 175.6(3) . . . . ?
C34 C29 C30 N3 -177.9(2) . . . . ?
C25 C29 C30 N3 -2.1(3) . . . . ?
C26 N3 C30 C31 -175.7(3) . . . . ?
C26 N3 C30 C29 1.9(3) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
N3 C30 C31 C32 178.0(3) . . . . ?
C30 C31 C32 C33 0.1(5) . . . . ?
C31 C32 C33 C34 -1.2(6) . . . . ?
C32 C33 C34 C29 1.6(5) . . . . ?
C30 C29 C34 C33 -0.9(4) . . . . ?
C25 C29 C34 C33 -175.2(3) . . . . ?
C24 C23 C35 C38 59.6(3) . . . . ?
C22 C23 C35 C38 175.3(2) . . . . ?
C24 C23 C35 C37 -61.3(3) . . . . ?
C22 C23 C35 C37 54.4(3) . . . . ?
C24 C23 C35 C36 178.5(2) . . . . ?
C22 C23 C35 C36 -65.8(3) . . . . ?

_refine_diff_density_max         0.780
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.149




####################################################################### 
# 
# 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_240222_s1_zjf_auto
_database_code_depnum_ccdc_archive 'CCDC 2335020'
loop_
_audit_author_name
_audit_author_address
'Jianfeng Zheng'
;Southwest Jiaotong University
China
;
_audit_update_record             
;
2024-02-24 deposited with the CCDC.	2024-08-27 downloaded from the CCDC.
;
_audit_creation_date             2024-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H12N2O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0963(4)
_cell_length_b                   10.5857(4)
_cell_length_c                   18.6757(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.516(4)
_cell_angle_gamma                90
_cell_volume                     1932.27(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2737
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8330
_cell_measurement_theta_min      3.8760
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8350
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.240
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.80  87.00   0.80    4.50    --   17.74  38.00 -60.00   99
  2  ω      0.00  33.60   0.80    4.50    --   17.74  77.00 150.00   42
  3  ω    -54.00  46.00   0.80    4.50    --   17.74 -19.00 120.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0277110000
_diffrn_orient_matrix_UB_12      -0.0216978000
_diffrn_orient_matrix_UB_13      0.0291314000
_diffrn_orient_matrix_UB_21      0.0645258000
_diffrn_orient_matrix_UB_22      0.0083300000
_diffrn_orient_matrix_UB_23      0.0254448000
_diffrn_orient_matrix_UB_31      -0.0182213000
_diffrn_orient_matrix_UB_32      0.0628264000
_diffrn_orient_matrix_UB_33      0.0066739000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2708
_reflns_number_total             3952
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.2025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1259
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11B,H11A)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C22(H22B,H22C,H22A), C23(H23C,H23A,H23B), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54742(12) 0.55320(11) 0.34772(7) 0.0379(3) Uani 1 1 d . . . . .
N1 N 0.75455(15) 0.65619(13) 0.34030(9) 0.0347(4) Uani 1 1 d . . . . .
C1 C 0.63146(18) 0.66776(16) 0.36750(10) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.96859(13) 0.56815(12) 0.37943(8) 0.0425(4) Uani 1 1 d . . . . .
N2 N 0.48504(17) 0.93460(15) 0.25003(10) 0.0415(4) Uani 1 1 d . . . . .
H2 H 0.486(2) 0.987(2) 0.2109(14) 0.070(8) Uiso 1 1 d . . . . .
C2 C 0.54430(19) 0.77196(16) 0.32822(10) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.41130(18) 0.81437(17) 0.33191(10) 0.0342(5) Uani 1 1 d . . . . .
C4 C 0.3161(2) 0.77636(19) 0.37047(12) 0.0439(5) Uani 1 1 d . . . . .
H4 H 0.334761 0.708395 0.402995 0.053 Uiso 1 1 calc R . . . .
C5 C 0.1943(2) 0.8408(2) 0.35968(12) 0.0486(6) Uani 1 1 d . . . . .
H5 H 0.129867 0.814945 0.384524 0.058 Uiso 1 1 calc R . . . .
C6 C 0.1661(2) 0.9439(2) 0.31227(12) 0.0508(6) Uani 1 1 d . . . . .
H6 H 0.083791 0.986799 0.306803 0.061 Uiso 1 1 calc R . . . .
C7 C 0.2574(2) 0.98414(19) 0.27311(12) 0.0462(6) Uani 1 1 d . . . . .
H7 H 0.238508 1.053453 0.241596 0.055 Uiso 1 1 calc R . . . .
C8 C 0.3777(2) 0.91735(17) 0.28265(11) 0.0364(5) Uani 1 1 d . . . . .
C9 C 0.58389(19) 0.84476(17) 0.27666(11) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.7091(2) 0.82748(18) 0.24959(12) 0.0462(5) Uani 1 1 d . . . . .
H10A H 0.779968 0.885465 0.274763 0.055 Uiso 1 1 calc R . . . .
H10B H 0.689135 0.844258 0.196903 0.055 Uiso 1 1 calc R . . . .
C11 C 0.7570(2) 0.69176(19) 0.26531(11) 0.0452(5) Uani 1 1 d . . . . .
H11B H 0.697855 0.635749 0.230256 0.054 Uiso 1 1 calc R . . . .
H11A H 0.849266 0.683104 0.259313 0.054 Uiso 1 1 calc R . . . .
C12 C 0.85631(19) 0.59591(16) 0.38921(11) 0.0333(4) Uani 1 1 d . . . . .
C13 C 0.79948(18) 0.56269(16) 0.45461(10) 0.0324(4) Uani 1 1 d . . . . .
H13 H 0.869460 0.559078 0.501617 0.039 Uiso 1 1 calc R . . . .
C14 C 0.69041(18) 0.66556(16) 0.45280(10) 0.0316(4) Uani 1 1 d . . . . .
H14 H 0.620290 0.629872 0.474880 0.038 Uiso 1 1 calc R . . . .
C15 C 0.72755(19) 0.43855(16) 0.43292(10) 0.0330(4) Uani 1 1 d . . . . .
C16 C 0.7807(2) 0.32321(17) 0.46048(11) 0.0408(5) Uani 1 1 d . . . . .
H16 H 0.863264 0.320322 0.496380 0.049 Uiso 1 1 calc R . . . .
C17 C 0.7134(2) 0.21240(18) 0.43564(12) 0.0484(6) Uani 1 1 d . . . . .
H17 H 0.751186 0.135198 0.453979 0.058 Uiso 1 1 calc R . . . .
C18 C 0.5904(2) 0.21643(18) 0.38372(12) 0.0458(5) Uani 1 1 d . . . . .
H18 H 0.544297 0.141605 0.367578 0.055 Uiso 1 1 calc R . . . .
C19 C 0.5342(2) 0.33028(17) 0.35510(11) 0.0416(5) Uani 1 1 d . . . . .
H19 H 0.450570 0.332437 0.320062 0.050 Uiso 1 1 calc R . . . .
C20 C 0.60402(19) 0.44119(16) 0.37924(10) 0.0333(4) Uani 1 1 d . . . . .
C21 C 0.7457(2) 0.78749(17) 0.49604(11) 0.0389(5) Uani 1 1 d . . . . .
C22 C 0.8082(3) 0.7479(2) 0.57734(12) 0.0638(7) Uani 1 1 d . . . . .
H22B H 0.829944 0.821972 0.607639 0.096 Uiso 1 1 calc GR . . . .
H22C H 0.889912 0.699691 0.580306 0.096 Uiso 1 1 calc GR . . . .
H22A H 0.743306 0.697368 0.594462 0.096 Uiso 1 1 calc GR . . . .
C23 C 0.8549(2) 0.85584(19) 0.46718(14) 0.0538(6) Uani 1 1 d . . . . .
H23C H 0.815668 0.885323 0.417798 0.081 Uiso 1 1 calc GR . . . .
H23A H 0.928627 0.798758 0.466924 0.081 Uiso 1 1 calc GR . . . .
H23B H 0.889001 0.926464 0.498654 0.081 Uiso 1 1 calc GR . . . .
C24 C 0.6288(2) 0.87991(19) 0.49521(13) 0.0506(6) Uani 1 1 d . . . . .
H24A H 0.596604 0.914907 0.446519 0.076 Uiso 1 1 calc GR . . . .
H24B H 0.661092 0.946694 0.529974 0.076 Uiso 1 1 calc GR . . . .
H24C H 0.555272 0.836096 0.508615 0.076 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.473(2) . ?
O1 C20 1.382(2) . ?
N1 C1 1.461(2) . ?
N1 C11 1.456(2) . ?
N1 C12 1.352(2) . ?
C1 C2 1.485(2) . ?
C1 C14 1.555(3) . ?
O2 C12 1.228(2) . ?
N2 H2 0.92(2) . ?
N2 C8 1.382(2) . ?
N2 C9 1.378(2) . ?
C2 C3 1.434(2) . ?
C2 C9 1.369(3) . ?
C3 C4 1.397(3) . ?
C3 C8 1.412(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(3) . ?
C9 C10 1.486(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.521(3) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C12 C13 1.515(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.543(2) . ?
C13 C15 1.507(2) . ?
C14 H14 0.9800 . ?
C14 C21 1.550(3) . ?
C15 C16 1.380(2) . ?
C15 C20 1.391(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(2) . ?
C21 C22 1.549(3) . ?
C21 C23 1.525(3) . ?
C21 C24 1.530(3) . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 C1 116.66(13) . . ?
C11 N1 C1 122.26(15) . . ?
C12 N1 C1 111.92(15) . . ?
C12 N1 C11 125.36(16) . . ?
O1 C1 C2 104.76(14) . . ?
O1 C1 C14 107.05(13) . . ?
N1 C1 O1 109.30(13) . . ?
N1 C1 C2 109.93(14) . . ?
N1 C1 C14 102.38(14) . . ?
C2 C1 C14 122.99(15) . . ?
C8 N2 H2 126.6(14) . . ?
C9 N2 H2 123.5(14) . . ?
C9 N2 C8 109.08(17) . . ?
C3 C2 C1 130.91(16) . . ?
C9 C2 C1 121.62(17) . . ?
C9 C2 C3 107.44(16) . . ?
C4 C3 C2 135.10(18) . . ?
C4 C3 C8 118.30(18) . . ?
C8 C3 C2 106.60(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.13(19) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.21(19) . . ?
C8 C7 H7 121.4 . . ?
N2 C8 C3 107.58(16) . . ?
C7 C8 N2 129.68(19) . . ?
C7 C8 C3 122.74(19) . . ?
N2 C9 C10 124.28(18) . . ?
C2 C9 N2 109.24(17) . . ?
C2 C9 C10 126.40(17) . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
C9 C10 C11 107.88(16) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
N1 C11 C10 110.41(15) . . ?
N1 C11 H11B 109.6 . . ?
N1 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
H11B C11 H11A 108.1 . . ?
N1 C12 C13 106.09(15) . . ?
O2 C12 N1 125.87(18) . . ?
O2 C12 C13 127.92(17) . . ?
C12 C13 H13 113.4 . . ?
C12 C13 C14 103.35(14) . . ?
C14 C13 H13 113.4 . . ?
C15 C13 C12 103.89(14) . . ?
C15 C13 H13 113.4 . . ?
C15 C13 C14 108.44(15) . . ?
C1 C14 H14 107.8 . . ?
C13 C14 C1 96.94(14) . . ?
C13 C14 H14 107.8 . . ?
C13 C14 C21 114.47(15) . . ?
C21 C14 C1 121.11(15) . . ?
C21 C14 H14 107.8 . . ?
C16 C15 C13 123.71(17) . . ?
C16 C15 C20 118.76(17) . . ?
C20 C15 C13 117.45(15) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.01(19) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.65(18) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.81(18) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.16(19) . . ?
C20 C19 H19 120.4 . . ?
O1 C20 C15 121.64(16) . . ?
O1 C20 C19 117.78(16) . . ?
C19 C20 C15 120.58(17) . . ?
C22 C21 C14 106.87(15) . . ?
C23 C21 C14 114.11(16) . . ?
C23 C21 C22 108.80(18) . . ?
C23 C21 C24 108.49(16) . . ?
C24 C21 C14 110.53(15) . . ?
C24 C21 C22 107.85(17) . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
C21 C23 H23C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23C C23 H23A 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 58.2(2) . . . . ?
O1 C1 C2 C9 -119.44(18) . . . . ?
O1 C1 C14 C13 74.86(15) . . . . ?
O1 C1 C14 C21 -161.02(14) . . . . ?
N1 C1 C2 C3 175.58(18) . . . . ?
N1 C1 C2 C9 -2.1(2) . . . . ?
N1 C1 C14 C13 -40.06(15) . . . . ?
N1 C1 C14 C21 84.06(18) . . . . ?
N1 C12 C13 C14 -27.48(18) . . . . ?
N1 C12 C13 C15 85.70(16) . . . . ?
C1 O1 C20 C15 6.7(2) . . . . ?
C1 O1 C20 C19 -172.70(16) . . . . ?
C1 N1 C11 C10 55.0(2) . . . . ?
C1 N1 C12 O2 176.51(16) . . . . ?
C1 N1 C12 C13 0.37(19) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C2 C3 C8 179.92(18) . . . . ?
C1 C2 C9 N2 -179.20(17) . . . . ?
C1 C2 C9 C10 3.9(3) . . . . ?
C1 C14 C21 C22 -174.67(17) . . . . ?
C1 C14 C21 C23 -54.4(2) . . . . ?
C1 C14 C21 C24 68.2(2) . . . . ?
O2 C12 C13 C14 156.49(17) . . . . ?
O2 C12 C13 C15 -90.3(2) . . . . ?
N2 C9 C10 C11 -155.42(18) . . . . ?
C2 C1 C14 C13 -164.02(16) . . . . ?
C2 C1 C14 C21 -39.9(2) . . . . ?
C2 C3 C4 C5 -179.6(2) . . . . ?
C2 C3 C8 N2 0.9(2) . . . . ?
C2 C3 C8 C7 -178.43(17) . . . . ?
C2 C9 C10 C11 21.0(3) . . . . ?
C3 C2 C9 N2 2.6(2) . . . . ?
C3 C2 C9 C10 -174.25(19) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C3 C8 N2 -178.41(17) . . . . ?
C4 C3 C8 C7 2.3(3) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 N2 178.72(19) . . . . ?
C6 C7 C8 C3 -2.2(3) . . . . ?
C8 N2 C9 C2 -2.1(2) . . . . ?
C8 N2 C9 C10 174.83(18) . . . . ?
C8 C3 C4 C5 -0.6(3) . . . . ?
C9 N2 C8 C3 0.7(2) . . . . ?
C9 N2 C8 C7 179.9(2) . . . . ?
C9 C2 C3 C4 176.9(2) . . . . ?
C9 C2 C3 C8 -2.1(2) . . . . ?
C9 C10 C11 N1 -45.7(2) . . . . ?
C11 N1 C1 O1 85.89(19) . . . . ?
C11 N1 C1 C2 -28.6(2) . . . . ?
C11 N1 C1 C14 -160.84(16) . . . . ?
C11 N1 C12 O2 4.2(3) . . . . ?
C11 N1 C12 C13 -171.96(16) . . . . ?
C12 N1 C1 O1 -86.72(17) . . . . ?
C12 N1 C1 C2 158.81(15) . . . . ?
C12 N1 C1 C14 26.55(18) . . . . ?
C12 N1 C11 C10 -133.46(19) . . . . ?
C12 C13 C14 C1 40.70(16) . . . . ?
C12 C13 C14 C21 -88.15(18) . . . . ?
C12 C13 C15 C16 103.0(2) . . . . ?
C12 C13 C15 C20 -73.6(2) . . . . ?
C13 C14 C21 C22 -59.2(2) . . . . ?
C13 C14 C21 C23 61.1(2) . . . . ?
C13 C14 C21 C24 -176.32(17) . . . . ?
C13 C15 C16 C17 -176.57(19) . . . . ?
C13 C15 C20 O1 -1.2(3) . . . . ?
C13 C15 C20 C19 178.17(17) . . . . ?
C14 C1 C2 C3 -63.9(3) . . . . ?
C14 C1 C2 C9 118.4(2) . . . . ?
C14 C13 C15 C16 -147.50(18) . . . . ?
C14 C13 C15 C20 35.9(2) . . . . ?
C15 C13 C14 C1 -69.12(17) . . . . ?
C15 C13 C14 C21 162.03(15) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C15 C20 O1 -177.95(16) . . . . ?
C16 C15 C20 C19 1.4(3) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 O1 177.83(17) . . . . ?
C18 C19 C20 C15 -1.5(3) . . . . ?
C20 O1 C1 N1 64.05(18) . . . . ?
C20 O1 C1 C2 -178.19(15) . . . . ?
C20 O1 C1 C14 -46.13(19) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.054
_oxdiff_exptl_absorpt_empirical_full_min 0.955
