# 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_231201
_database_code_depnum_ccdc_archive 'CCDC 2348104'
loop_
_audit_author_name
_audit_author_address
WP-B
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-11-04 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            'C30 H25 N O4'
_chemical_formula_weight         463.51

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   8.7819(5)
_cell_length_b                   10.3472(6)
_cell_length_c                   13.4614(8)
_cell_angle_alpha                97.784(2)
_cell_angle_beta                 97.527(2)
_cell_angle_gamma                91.588(2)
_cell_volume                     1200.21(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4221
_cell_measurement_theta_min      2.342
_cell_measurement_theta_max      25.016

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17738
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_full        25.016
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4221
_reflns_number_gt                2813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0365P)²+0.9829P] 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         4221
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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 0.2851(3) 0.4016(3) 0.8510(2) 0.0491(7) Uani 1 1 d . . . . .
O1 O 0.0941(2) 0.2376(2) 0.78048(16) 0.0527(6) Uani 1 1 d . . . . .
O2 O -0.0255(3) 0.3438(3) 0.39418(19) 0.0809(8) Uani 1 1 d . . . . .
O3 O -0.2352(3) 0.3273(3) 0.4799(2) 0.0759(8) Uani 1 1 d . . . . .
O4 O 0.5514(2) 0.1214(2) 0.71450(18) 0.0576(6) Uani 1 1 d . . . . .
C1 C 0.3980(3) 0.4611(3) 0.8082(2) 0.0454(8) Uani 1 1 d . . . . .
C2 C 0.4699(4) 0.5832(3) 0.8381(3) 0.0560(9) Uani 1 1 d . . . . .
H2 H 0.446796 0.636914 0.894836 0.067 Uiso 1 1 calc R U . . .
C3 C 0.5776(4) 0.6227(4) 0.7807(3) 0.0698(11) Uani 1 1 d . . . . .
H3 H 0.628076 0.704258 0.799814 0.084 Uiso 1 1 calc R U . . .
C4 C 0.6121(4) 0.5453(4) 0.6964(3) 0.0708(11) Uani 1 1 d . . . . .
H4 H 0.684532 0.574879 0.659151 0.085 Uiso 1 1 calc R U . . .
C5 C 0.5389(4) 0.4223(4) 0.6663(3) 0.0579(10) Uani 1 1 d . . . . .
H5 H 0.561820 0.369344 0.609172 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4326(3) 0.3810(3) 0.7226(2) 0.0444(8) Uani 1 1 d . . . . .
C7 C 0.3289(3) 0.2590(3) 0.7049(2) 0.0439(8) Uani 1 1 d . . . . .
C8 C 0.1844(3) 0.2751(3) 0.6335(2) 0.0437(8) Uani 1 1 d . . . . .
C9 C 0.1688(4) 0.3008(3) 0.5339(2) 0.0532(9) Uani 1 1 d . . . . .
H9 H 0.253003 0.308425 0.499458 0.064 Uiso 1 1 calc R U . . .
C10 C 0.0221(4) 0.3141(3) 0.4901(3) 0.0549(9) Uani 1 1 d . . . . .
C11 C -0.1895(5) 0.3384(4) 0.3839(3) 0.0786(12) Uani 1 1 d . . . . .
H11A H -0.228812 0.416938 0.359922 0.094 Uiso 1 1 calc R U . . .
H11B H -0.230683 0.263844 0.335275 0.094 Uiso 1 1 calc R U . . .
C12 C -0.1036(4) 0.3040(3) 0.5412(3) 0.0545(9) Uani 1 1 d . . . . .
C13 C -0.0912(4) 0.2790(3) 0.6390(3) 0.0556(9) Uani 1 1 d . . . . .
H13 H -0.175812 0.272469 0.673265 0.067 Uiso 1 1 calc R U . . .
C14 C 0.0572(3) 0.2644(3) 0.6828(2) 0.0458(8) Uani 1 1 d . . . . .
C15 C 0.2579(3) 0.2648(3) 0.8080(2) 0.0471(8) Uani 1 1 d . . . . .
C16 C 0.2358(4) 0.4540(4) 0.9466(2) 0.0583(10) Uani 1 1 d . . . . .
H16A H 0.324800 0.467371 0.998382 0.070 Uiso 1 1 calc R U . . .
H16B H 0.165995 0.390384 0.965809 0.070 Uiso 1 1 calc R U . . .
C17 C 0.1571(4) 0.5808(3) 0.9429(2) 0.0488(8) Uani 1 1 d . . . . .
C18 C 0.0644(4) 0.6056(3) 0.8582(3) 0.0579(9) Uani 1 1 d . . . . .
H18 H 0.050397 0.543280 0.800672 0.069 Uiso 1 1 calc R U . . .
C19 C -0.0083(4) 0.7219(4) 0.8572(3) 0.0725(11) Uani 1 1 d . . . . .
H19 H -0.069713 0.737635 0.798799 0.087 Uiso 1 1 calc R U . . .
C20 C 0.0085(5) 0.8130(4) 0.9401(4) 0.0825(13) Uani 1 1 d . . . . .
H20 H -0.041676 0.890887 0.938840 0.099 Uiso 1 1 calc R U . . .
C21 C 0.0991(6) 0.7907(4) 1.0252(4) 0.0877(14) Uani 1 1 d . . . . .
H21 H 0.110266 0.853295 1.082479 0.105 Uiso 1 1 calc R U . . .
C22 C 0.1754(5) 0.6746(4) 1.0272(3) 0.0701(11) Uani 1 1 d . . . . .
H22 H 0.238568 0.660359 1.085420 0.084 Uiso 1 1 calc R U . . .
C23 C 0.3192(4) 0.1744(3) 0.8823(3) 0.0620(10) Uani 1 1 d . . . . .
H23A H 0.430165 0.188065 0.895221 0.074 Uiso 1 1 calc R U . . .
H23B H 0.280032 0.201052 0.945711 0.074 Uiso 1 1 calc R U . . .
C24 C 0.2845(6) 0.0368(4) 0.8540(3) 0.0848(13) Uani 1 1 d . . . . .
H24 H 0.185032 0.010329 0.823961 0.102 Uiso 1 1 calc R U . . .
C25 C 0.3850(7) -0.0559(5) 0.8677(4) 0.119(2) Uani 1 1 d . . . . .
H25A H 0.485410 -0.032956 0.897513 0.142 Uiso 1 1 calc R U . . .
H25B H 0.354538 -0.143328 0.847497 0.142 Uiso 1 1 calc R U . . .
C26 C 0.4023(4) 0.1347(3) 0.6717(3) 0.0484(8) Uani 1 1 d . . . . .
C27 C 0.3544(4) 0.0272(4) 0.6075(3) 0.0627(10) Uani 1 1 d . . . . .
H27 H 0.258949 0.012569 0.567767 0.075 Uiso 1 1 calc R U . . .
C28 C 0.4755(5) -0.0607(4) 0.6110(3) 0.0666(11) Uani 1 1 d . . . . .
H28 H 0.473725 -0.144040 0.574802 0.080 Uiso 1 1 calc R U . . .
C29 C 0.5914(4) -0.0017(3) 0.6754(3) 0.0619(10) Uani 1 1 d . . . . .
C30 C 0.7500(4) -0.0379(4) 0.7102(4) 0.0913(15) Uani 1 1 d . . . . .
H30A H 0.767673 -0.122937 0.676481 0.137 Uiso 1 1 calc R U . . .
H30B H 0.762187 -0.039056 0.781945 0.137 Uiso 1 1 calc R U . . .
H30C H 0.822544 0.024855 0.694533 0.137 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
N1 C1 1.380(4) . ?
N1 C16 1.452(4) . ?
N1 C15 1.455(4) . ?
O1 C14 1.380(4) . ?
O1 C15 1.447(4) . ?
O2 C10 1.382(4) . ?
O2 C11 1.428(4) . ?
O3 C12 1.377(4) . ?
O3 C11 1.419(5) . ?
O4 C26 1.379(4) . ?
O4 C29 1.384(4) . ?
C1 C2 1.382(5) . ?
C1 C6 1.398(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(4) . ?
C7 C26 1.495(4) . ?
C7 C8 1.516(4) . ?
C7 C15 1.590(4) . ?
C8 C14 1.382(4) . ?
C8 C9 1.392(4) . ?
C9 C10 1.363(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.384(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.367(5) . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C15 C23 1.518(4) . ?
C16 C17 1.504(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.370(5) . ?
C17 C22 1.379(5) . ?
C18 C19 1.379(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.349(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.357(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.437(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.336(6) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9300 . ?
C25 H25B 0.9300 . ?
C26 C27 1.334(5) . ?
C27 C28 1.419(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.323(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.485(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C1 N1 C16 123.6(3) . . ?
C1 N1 C15 111.6(3) . . ?
C16 N1 C15 122.2(3) . . ?
C14 O1 C15 107.1(2) . . ?
C10 O2 C11 105.3(3) . . ?
C12 O3 C11 105.9(3) . . ?
C26 O4 C29 106.2(3) . . ?
N1 C1 C2 128.5(3) . . ?
N1 C1 C6 110.5(3) . . ?
C2 C1 C6 120.9(3) . . ?
C1 C2 C3 117.6(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 121.9(4) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 C7 130.4(3) . . ?
C1 C6 C7 108.9(3) . . ?
C26 C7 C6 115.8(3) . . ?
C26 C7 C8 110.7(3) . . ?
C6 C7 C8 111.0(2) . . ?
C26 C7 C15 115.7(2) . . ?
C6 C7 C15 102.7(3) . . ?
C8 C7 C15 99.5(2) . . ?
C14 C8 C9 120.8(3) . . ?
C14 C8 C7 109.6(3) . . ?
C9 C8 C7 129.5(3) . . ?
C10 C9 C8 115.7(3) . . ?
C10 C9 H9 122.1 . . ?
C8 C9 H9 122.1 . . ?
C9 C10 O2 127.8(3) . . ?
C9 C10 C12 122.4(3) . . ?
O2 C10 C12 109.8(3) . . ?
O3 C11 O2 108.5(3) . . ?
O3 C11 H11A 110.0 . . ?
O2 C11 H11A 110.0 . . ?
O3 C11 H11B 110.0 . . ?
O2 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C13 C12 O3 127.5(3) . . ?
C13 C12 C10 122.9(3) . . ?
O3 C12 C10 109.5(3) . . ?
C12 C13 C14 114.5(3) . . ?
C12 C13 H13 122.8 . . ?
C14 C13 H13 122.8 . . ?
C13 C14 O1 123.5(3) . . ?
C13 C14 C8 123.6(3) . . ?
O1 C14 C8 112.9(3) . . ?
O1 C15 N1 109.0(2) . . ?
O1 C15 C23 108.9(3) . . ?
N1 C15 C23 111.8(3) . . ?
O1 C15 C7 106.4(2) . . ?
N1 C15 C7 102.4(2) . . ?
C23 C15 C7 117.9(3) . . ?
N1 C16 C17 113.2(3) . . ?
N1 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N1 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C22 118.5(3) . . ?
C18 C17 C16 121.8(3) . . ?
C22 C17 C16 119.7(3) . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.9(4) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C15 117.6(3) . . ?
C24 C23 H23A 107.9 . . ?
C15 C23 H23A 107.9 . . ?
C24 C23 H23B 107.9 . . ?
C15 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C25 C24 C23 124.6(5) . . ?
C25 C24 H24 117.7 . . ?
C23 C24 H24 117.7 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
C27 C26 O4 109.3(3) . . ?
C27 C26 C7 133.8(3) . . ?
O4 C26 C7 116.9(3) . . ?
C26 C27 C28 107.5(3) . . ?
C26 C27 H27 126.2 . . ?
C28 C27 H27 126.2 . . ?
C29 C28 C27 107.1(3) . . ?
C29 C28 H28 126.5 . . ?
C27 C28 H28 126.5 . . ?
C28 C29 O4 109.9(3) . . ?
C28 C29 C30 134.1(4) . . ?
O4 C29 C30 116.0(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_exp_13503
_database_code_depnum_ccdc_archive 'CCDC 2348106'
loop_
_audit_author_name
_audit_author_address
WP-D
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-11-04 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            'C25 H25 N O5 S'
_chemical_formula_weight         451.52

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'
S S 0.3331 0.5567 '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                   12.9521(5)
_cell_length_b                   19.0400(8)
_cell_length_c                   9.3837(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.104(4)
_cell_angle_gamma                90
_cell_volume                     2300.97(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3619
_cell_measurement_theta_min      4.1470
_cell_measurement_theta_max      70.7620

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.552
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_T_min  0.92573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8265
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.432
_diffrn_reflns_theta_max         67.244
_diffrn_reflns_theta_full        67.244
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4108
_reflns_number_gt                3251
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0506P)²+0.4451P] 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         4108
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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
S1 S 0.17314(4) 0.64263(3) 0.67423(6) 0.05406(17) Uani 1 1 d . . . . .
N1 N 0.17060(11) 0.49284(8) 0.46385(17) 0.0446(4) Uani 1 1 d . . . . .
O1 O 0.53842(13) 0.64624(9) 1.01212(18) 0.0745(5) Uani 1 1 d . . . . .
O2 O 0.64816(11) 0.55752(9) 0.95244(17) 0.0662(4) Uani 1 1 d . . . . .
O3 O 0.38712(11) 0.45992(9) 0.60271(18) 0.0675(5) Uani 1 1 d . . . . .
H3 H 0.432418 0.430841 0.592295 0.101 Uiso 1 1 calc R U . . .
O4 O 0.28537(11) 0.57731(8) 0.40657(15) 0.0534(4) Uani 1 1 d . . . . .
O5 O 0.52102(12) 0.36150(9) 0.5469(2) 0.0675(4) Uani 1 1 d . . . . .
H5 H 0.578733 0.378991 0.545239 0.101 Uiso 1 1 calc R U . . .
C1 C 0.35743(14) 0.56182(10) 0.7320(2) 0.0440(4) Uani 1 1 d . . . . .
C2 C 0.39039(16) 0.61123(11) 0.8376(2) 0.0503(5) Uani 1 1 d . . . . .
H2 H 0.346679 0.647125 0.861485 0.060 Uiso 1 1 calc R U . . .
C3 C 0.48916(16) 0.60493(11) 0.9044(2) 0.0517(5) Uani 1 1 d . . . . .
C4 C 0.55450(14) 0.55261(11) 0.8705(2) 0.0499(5) Uani 1 1 d . . . . .
C5 C 0.52563(15) 0.50340(11) 0.7694(2) 0.0525(5) Uani 1 1 d . . . . .
H5A H 0.570633 0.467999 0.746908 0.063 Uiso 1 1 calc R U . . .
C6 C 0.42462(15) 0.50873(11) 0.7010(2) 0.0490(5) Uani 1 1 d . . . . .
C7 C 0.64133(18) 0.61932(13) 1.0368(3) 0.0677(7) Uani 1 1 d . . . . .
H7A H 0.657793 0.608262 1.137524 0.081 Uiso 1 1 calc R U . . .
H7B H 0.690529 0.654164 1.010399 0.081 Uiso 1 1 calc R U . . .
C8 C 0.24726(14) 0.56121(10) 0.6560(2) 0.0443(4) Uani 1 1 d . . . . .
C9 C 0.17802(14) 0.50492(11) 0.7067(2) 0.0480(5) Uani 1 1 d . . . . .
C10 C 0.15309(17) 0.48940(14) 0.8423(2) 0.0619(6) Uani 1 1 d . . . . .
H10 H 0.181698 0.514753 0.921569 0.074 Uiso 1 1 calc R U . . .
C11 C 0.0840(2) 0.43484(15) 0.8571(3) 0.0747(7) Uani 1 1 d . . . . .
H11 H 0.066944 0.422932 0.947835 0.090 Uiso 1 1 calc R U . . .
C12 C 0.04040(19) 0.39802(13) 0.7393(3) 0.0731(7) Uani 1 1 d . . . . .
H12 H -0.006307 0.362054 0.752104 0.088 Uiso 1 1 calc R U . . .
C13 C 0.06434(16) 0.41324(11) 0.6023(3) 0.0599(6) Uani 1 1 d . . . . .
H13 H 0.035068 0.388243 0.522928 0.072 Uiso 1 1 calc R U . . .
C14 C 0.13354(14) 0.46714(11) 0.5892(2) 0.0474(5) Uani 1 1 d . . . . .
C15 C 0.23986(13) 0.54572(10) 0.4944(2) 0.0436(4) Uani 1 1 d . . . . .
C16 C 0.13889(17) 0.46667(12) 0.3201(2) 0.0563(5) Uani 1 1 d . . . . .
H16A H 0.168634 0.496742 0.251675 0.068 Uiso 1 1 calc R U . . .
H16B H 0.063946 0.470263 0.301768 0.068 Uiso 1 1 calc R U . . .
C17 C 0.17012(15) 0.39183(11) 0.2941(2) 0.0485(5) Uani 1 1 d . . . . .
C18 C 0.10134(18) 0.34827(12) 0.2140(2) 0.0598(6) Uani 1 1 d . . . . .
H18 H 0.034819 0.364240 0.183322 0.072 Uiso 1 1 calc R U . . .
C19 C 0.1304(2) 0.28116(13) 0.1791(3) 0.0774(7) Uani 1 1 d . . . . .
H19 H 0.083759 0.252447 0.123911 0.093 Uiso 1 1 calc R U . . .
C20 C 0.2280(2) 0.25672(14) 0.2256(3) 0.0818(8) Uani 1 1 d . . . . .
H20 H 0.247646 0.211589 0.201834 0.098 Uiso 1 1 calc R U . . .
C21 C 0.2959(2) 0.29904(14) 0.3068(3) 0.0764(7) Uani 1 1 d . . . . .
H21 H 0.361294 0.282163 0.340628 0.092 Uiso 1 1 calc R U . . .
C22 C 0.26817(18) 0.36668(13) 0.3392(3) 0.0628(6) Uani 1 1 d . . . . .
H22 H 0.315941 0.395590 0.391867 0.075 Uiso 1 1 calc R U . . .
C23 C 0.2398(2) 0.70986(12) 0.5830(3) 0.0687(6) Uani 1 1 d . . . . .
H23A H 0.312069 0.712248 0.622407 0.082 Uiso 1 1 calc R U . . .
H23B H 0.237213 0.698878 0.481728 0.082 Uiso 1 1 calc R U . . .
C24 C 0.1867(3) 0.77975(15) 0.6033(4) 0.1077(12) Uani 1 1 d . . . . .
H24A H 0.114961 0.776630 0.565688 0.162 Uiso 1 1 calc R U . . .
H24B H 0.220053 0.815877 0.553446 0.162 Uiso 1 1 calc R U . . .
H24C H 0.191515 0.790890 0.703548 0.162 Uiso 1 1 calc R U . . .
C25 C 0.5272(2) 0.30568(16) 0.6430(4) 0.0974(10) Uani 1 1 d . . . . .
H25A H 0.579399 0.273238 0.619087 0.146 Uiso 1 1 calc R U . . .
H25B H 0.461288 0.282217 0.637832 0.146 Uiso 1 1 calc R U . . .
H25C H 0.545127 0.323051 0.738484 0.146 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
S1 C23 1.810(3) . ?
S1 C8 1.8411(19) . ?
N1 C15 1.359(2) . ?
N1 C14 1.405(3) . ?
N1 C16 1.456(2) . ?
O1 C3 1.382(2) . ?
O1 C7 1.424(3) . ?
O2 C4 1.369(2) . ?
O2 C7 1.426(3) . ?
O3 C6 1.362(2) . ?
O3 H3 0.8200 . ?
O4 C15 1.222(2) . ?
O5 C25 1.391(3) . ?
O5 H5 0.8200 . ?
C1 C6 1.385(3) . ?
C1 C2 1.399(3) . ?
C1 C8 1.526(2) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(3) . ?
C4 C5 1.357(3) . ?
C5 C6 1.399(3) . ?
C5 H5A 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.507(3) . ?
C8 C15 1.538(3) . ?
C9 C10 1.378(3) . ?
C9 C14 1.389(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C16 C17 1.508(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.380(3) . ?
C17 C22 1.381(3) . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.519(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C23 S1 C8 105.78(10) . . ?
C15 N1 C14 110.99(16) . . ?
C15 N1 C16 124.35(18) . . ?
C14 N1 C16 124.66(17) . . ?
C3 O1 C7 105.38(17) . . ?
C4 O2 C7 105.34(17) . . ?
C6 O3 H3 109.5 . . ?
C25 O5 H5 109.5 . . ?
C6 C1 C2 119.24(17) . . ?
C6 C1 C8 118.25(17) . . ?
C2 C1 C8 122.39(17) . . ?
C3 C2 C1 117.72(19) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 121.96(19) . . ?
C4 C3 O1 109.62(18) . . ?
C2 C3 O1 128.4(2) . . ?
C5 C4 C3 122.31(18) . . ?
C5 C4 O2 127.0(2) . . ?
C3 C4 O2 110.70(18) . . ?
C4 C5 C6 116.47(19) . . ?
C4 C5 H5A 121.8 . . ?
C6 C5 H5A 121.8 . . ?
O3 C6 C1 116.99(17) . . ?
O3 C6 C5 120.68(18) . . ?
C1 C6 C5 122.29(19) . . ?
O1 C7 O2 108.61(17) . . ?
O1 C7 H7A 110.0 . . ?
O2 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
O2 C7 H7B 110.0 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C1 114.61(16) . . ?
C9 C8 C15 101.42(16) . . ?
C1 C8 C15 114.81(15) . . ?
C9 C8 S1 103.65(12) . . ?
C1 C8 S1 114.91(14) . . ?
C15 C8 S1 105.93(13) . . ?
C10 C9 C14 120.3(2) . . ?
C10 C9 C8 130.5(2) . . ?
C14 C9 C8 109.18(17) . . ?
C9 C10 C11 118.0(2) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 116.8(2) . . ?
C14 C13 H13 121.6 . . ?
C12 C13 H13 121.6 . . ?
C13 C14 C9 122.3(2) . . ?
C13 C14 N1 128.2(2) . . ?
C9 C14 N1 109.53(17) . . ?
O4 C15 N1 125.28(18) . . ?
O4 C15 C8 125.95(18) . . ?
N1 C15 C8 108.71(17) . . ?
N1 C16 C17 114.78(17) . . ?
N1 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
N1 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C22 118.6(2) . . ?
C18 C17 C16 119.16(19) . . ?
C22 C17 C16 122.12(19) . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C24 C23 S1 108.4(2) . . ?
C24 C23 H23A 110.0 . . ?
S1 C23 H23A 110.0 . . ?
C24 C23 H23B 110.0 . . ?
S1 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
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 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_230831c
_database_code_depnum_ccdc_archive 'CCDC 2348107'
loop_
_audit_author_name
_audit_author_address
WP-E
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-11-04 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            'C26 H23 N2 O4'
_chemical_formula_weight         427.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

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

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

_cell_length_a                   10.8116(11)
_cell_length_b                   14.9897(14)
_cell_length_c                   13.0257(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.585(3)
_cell_angle_gamma                90
_cell_volume                     2104.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3690
_cell_measurement_theta_min      2.075
_cell_measurement_theta_max      25.007

_exptl_crystal_description       block
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9970
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.075
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3690
_reflns_number_gt                2405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0691P)²+0.8317P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0187(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     290
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.040
_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 0.4182(2) 0.13691(13) 0.23456(19) 0.0451(6) Uani 1 1 d . . . . .
N2 N 0.2378(2) 0.03777(13) 0.40733(16) 0.0389(5) Uani 1 1 d . . . . .
O1 O 0.28004(19) 0.22075(12) 0.31530(18) 0.0577(6) Uani 1 1 d . . . . .
O2 O 0.07464(17) -0.07770(11) 0.33262(14) 0.0479(5) Uani 1 1 d . . . . .
H2 H 0.141666 -0.065105 0.363097 0.072 Uiso 1 1 calc R U . . .
O3 O -0.19683(18) 0.03567(15) 0.05645(15) 0.0597(6) Uani 1 1 d . . . . .
O4 O -0.0713(2) 0.15488(15) 0.02886(16) 0.0654(6) Uani 1 1 d . . . . .
C1 C 0.3152(2) 0.15019(17) 0.2848(2) 0.0415(7) Uani 1 1 d . . . . .
C2 C 0.2521(2) 0.05812(15) 0.29869(19) 0.0350(6) Uani 1 1 d . . . . .
C3 C 0.3448(2) -0.00358(16) 0.25324(19) 0.0355(6) Uani 1 1 d . . . . .
C4 C 0.4372(2) 0.04618(16) 0.2147(2) 0.0399(6) Uani 1 1 d . . . . .
C5 C 0.5297(3) 0.00850(19) 0.1644(2) 0.0509(7) Uani 1 1 d . . . . .
H5 H 0.590376 0.043411 0.137395 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5306(3) -0.0826(2) 0.1550(2) 0.0532(8) Uani 1 1 d . . . . .
H6 H 0.593254 -0.110156 0.121623 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4405(3) -0.13346(18) 0.1942(2) 0.0498(8) Uani 1 1 d . . . . .
H7 H 0.442949 -0.195205 0.187677 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3465(2) -0.09437(17) 0.2429(2) 0.0417(7) Uani 1 1 d . . . . .
H8 H 0.284830 -0.129154 0.268597 0.050 Uiso 1 1 calc R U . . .
C9 C 0.5071(3) 0.20683(18) 0.2165(3) 0.0560(9) Uani 1 1 d . . . . .
H9A H 0.467068 0.264464 0.220999 0.067 Uiso 1 1 calc R U . . .
H9B H 0.533401 0.200648 0.147348 0.067 Uiso 1 1 calc R U . . .
C10 C 0.6185(3) 0.20356(16) 0.2922(2) 0.0449(7) Uani 1 1 d . . . . .
C11 C 0.6061(3) 0.2175(2) 0.3953(3) 0.0683(10) Uani 1 1 d . . . . .
H11 H 0.528646 0.231153 0.417449 0.082 Uiso 1 1 calc R U . . .
C12 C 0.7076(4) 0.2114(2) 0.4660(3) 0.0765(11) Uani 1 1 d . . . . .
H12 H 0.698160 0.220056 0.535594 0.092 Uiso 1 1 calc R U . . .
C13 C 0.8224(3) 0.1926(2) 0.4339(3) 0.0674(9) Uani 1 1 d . . . . .
H13 H 0.891287 0.188948 0.481294 0.081 Uiso 1 1 calc R U . . .
C14 C 0.8344(3) 0.1793(2) 0.3329(3) 0.0604(9) Uani 1 1 d . . . . .
H14 H 0.911994 0.166117 0.310733 0.072 Uiso 1 1 calc R U . . .
C15 C 0.7339(3) 0.18509(18) 0.2624(3) 0.0520(8) Uani 1 1 d . . . . .
H15 H 0.744405 0.176259 0.192990 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3553(3) 0.0308(2) 0.4720(2) 0.0529(8) Uani 1 1 d . U . . .
H16A H 0.416526 0.071983 0.448916 0.063 Uiso 1 1 calc R U . . .
H16B H 0.388284 -0.029311 0.470613 0.063 Uiso 1 1 calc R U . . .
C17 C 0.3216(4) 0.0546(3) 0.5772(3) 0.0755(11) Uani 1 1 d . U . . .
H17A H 0.294533 0.002268 0.613153 0.091 Uiso 1 1 calc R U . . .
H17B H 0.391585 0.081114 0.617371 0.091 Uiso 1 1 calc R U . . .
C18 C 0.2209(4) 0.1184(3) 0.5598(3) 0.1058(16) Uani 1 1 d . U . . .
H18 H 0.201685 0.164051 0.604265 0.127 Uiso 1 1 calc R U . . .
C19 C 0.1553(3) 0.0984(2) 0.4605(2) 0.0530(8) Uani 1 1 d . U . . .
H19A H 0.139598 0.152594 0.420914 0.064 Uiso 1 1 calc R U . . .
H19B H 0.076602 0.069582 0.469722 0.064 Uiso 1 1 calc R U . . .
C20 C 0.1265(2) 0.05229(15) 0.23869(19) 0.0343(6) Uani 1 1 d . . . . .
C21 C 0.0471(2) -0.01720(16) 0.25646(19) 0.0366(6) Uani 1 1 d . . . . .
C22 C -0.0642(3) -0.02921(18) 0.1973(2) 0.0443(7) Uani 1 1 d . . . . .
H22 H -0.117299 -0.076276 0.209160 0.053 Uiso 1 1 calc R U . . .
C23 C -0.0916(2) 0.03080(19) 0.1217(2) 0.0436(7) Uani 1 1 d . . . . .
C24 C -0.0158(3) 0.10054(19) 0.1041(2) 0.0448(7) Uani 1 1 d . . . . .
C25 C 0.0930(2) 0.11343(18) 0.1608(2) 0.0426(7) Uani 1 1 d . . . . .
H25 H 0.143907 0.161589 0.148202 0.051 Uiso 1 1 calc R U . . .
C26 C -0.1723(3) 0.1043(2) -0.0146(2) 0.0642(9) Uani 1 1 d . . . . .
H26A H -0.152218 0.078428 -0.079476 0.077 Uiso 1 1 calc R U . . .
H26B H -0.244754 0.142039 -0.027466 0.077 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
N1 C1 1.351(3) . ?
N1 C4 1.403(3) . ?
N1 C9 1.454(3) . ?
N2 C2 1.468(3) . ?
N2 C16 1.471(3) . ?
N2 C19 1.483(3) . ?
O1 C1 1.202(3) . ?
O2 C21 1.359(3) . ?
O2 H2 0.8200 . ?
O3 C23 1.367(3) . ?
O3 C26 1.423(4) . ?
O4 C24 1.375(3) . ?
O4 C26 1.411(4) . ?
C1 C2 1.557(3) . ?
C2 C20 1.513(3) . ?
C2 C3 1.518(3) . ?
C3 C8 1.368(3) . ?
C3 C4 1.374(4) . ?
C4 C5 1.362(4) . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.496(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.364(4) . ?
C10 C11 1.376(5) . ?
C11 C12 1.378(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.347(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.489(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.454(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.456(5) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.381(3) . ?
C20 C25 1.394(3) . ?
C21 C22 1.388(4) . ?
C22 C23 1.349(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(4) . ?
C24 C25 1.352(4) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 111.8(2) . . ?
C1 N1 C9 123.6(2) . . ?
C4 N1 C9 124.1(2) . . ?
C2 N2 C16 114.5(2) . . ?
C2 N2 C19 115.9(2) . . ?
C16 N2 C19 107.5(2) . . ?
C21 O2 H2 109.5 . . ?
C23 O3 C26 104.7(2) . . ?
C24 O4 C26 104.3(2) . . ?
O1 C1 N1 125.8(3) . . ?
O1 C1 C2 126.0(2) . . ?
N1 C1 C2 108.2(2) . . ?
N2 C2 C20 109.1(2) . . ?
N2 C2 C3 111.90(19) . . ?
C20 C2 C3 110.9(2) . . ?
N2 C2 C1 112.2(2) . . ?
C20 C2 C1 111.99(19) . . ?
C3 C2 C1 100.7(2) . . ?
C8 C3 C4 119.2(2) . . ?
C8 C3 C2 131.3(2) . . ?
C4 C3 C2 109.5(2) . . ?
C5 C4 C3 122.3(2) . . ?
C5 C4 N1 127.9(3) . . ?
C3 C4 N1 109.7(2) . . ?
C4 C5 C6 117.8(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 119.2(3) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N1 C9 C10 112.2(2) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 C9 121.7(3) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 121.2(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N2 C16 C17 104.3(3) . . ?
N2 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
N2 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C16 104.4(3) . . ?
C18 C17 H17A 110.9 . . ?
C16 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
C16 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C17 C18 C19 107.9(3) . . ?
C17 C18 H18 126.0 . . ?
C19 C18 H18 126.0 . . ?
C18 C19 N2 105.9(3) . . ?
C18 C19 H19A 110.6 . . ?
N2 C19 H19A 110.6 . . ?
C18 C19 H19B 110.6 . . ?
N2 C19 H19B 110.6 . . ?
H19A C19 H19B 108.7 . . ?
C21 C20 C25 119.3(2) . . ?
C21 C20 C2 120.1(2) . . ?
C25 C20 C2 120.5(2) . . ?
O2 C21 C20 121.5(2) . . ?
O2 C21 C22 116.6(2) . . ?
C20 C21 C22 121.9(2) . . ?
C23 C22 C21 116.6(3) . . ?
C23 C22 H22 121.7 . . ?
C21 C22 H22 121.7 . . ?
C22 C23 C24 122.4(3) . . ?
C22 C23 O3 127.8(3) . . ?
C24 C23 O3 109.7(2) . . ?
C25 C24 C23 121.9(2) . . ?
C25 C24 O4 128.0(3) . . ?
C23 C24 O4 109.9(2) . . ?
C24 C25 C20 117.9(2) . . ?
C24 C25 H25 121.0 . . ?
C20 C25 H25 121.0 . . ?
O4 C26 O3 107.8(2) . . ?
O4 C26 H26A 110.1 . . ?
O3 C26 H26A 110.1 . . ?
O4 C26 H26B 110.1 . . ?
O3 C26 H26B 110.1 . . ?
H26A C26 H26B 108.5 . . ?

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
C4 N1 C1 O1 176.5(3) . . . . ?
C9 N1 C1 O1 4.5(4) . . . . ?
C4 N1 C1 C2 -2.0(3) . . . . ?
C9 N1 C1 C2 -174.1(2) . . . . ?
C16 N2 C2 C20 173.2(2) . . . . ?
C19 N2 C2 C20 -60.9(3) . . . . ?
C16 N2 C2 C3 50.1(3) . . . . ?
C19 N2 C2 C3 176.1(2) . . . . ?
C16 N2 C2 C1 -62.2(3) . . . . ?
C19 N2 C2 C1 63.8(3) . . . . ?
O1 C1 C2 N2 -56.0(3) . . . . ?
N1 C1 C2 N2 122.5(2) . . . . ?
O1 C1 C2 C20 67.0(3) . . . . ?
N1 C1 C2 C20 -114.4(2) . . . . ?
O1 C1 C2 C3 -175.2(3) . . . . ?
N1 C1 C2 C3 3.4(3) . . . . ?
N2 C2 C3 C8 59.5(3) . . . . ?
C20 C2 C3 C8 -62.5(3) . . . . ?
C1 C2 C3 C8 178.8(3) . . . . ?
N2 C2 C3 C4 -123.0(2) . . . . ?
C20 C2 C3 C4 115.0(2) . . . . ?
C1 C2 C3 C4 -3.7(3) . . . . ?
C8 C3 C4 C5 1.3(4) . . . . ?
C2 C3 C4 C5 -176.5(3) . . . . ?
C8 C3 C4 N1 -179.3(2) . . . . ?
C2 C3 C4 N1 2.8(3) . . . . ?
C1 N1 C4 C5 178.8(3) . . . . ?
C9 N1 C4 C5 -9.2(5) . . . . ?
C1 N1 C4 C3 -0.4(3) . . . . ?
C9 N1 C4 C3 171.5(2) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
N1 C4 C5 C6 179.2(3) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C2 C3 C8 C7 177.2(3) . . . . ?
C6 C7 C8 C3 -0.9(4) . . . . ?
C1 N1 C9 C10 99.6(3) . . . . ?
C4 N1 C9 C10 -71.5(4) . . . . ?
N1 C9 C10 C15 115.0(3) . . . . ?
N1 C9 C10 C11 -63.6(3) . . . . ?
C15 C10 C11 C12 -1.0(4) . . . . ?
C9 C10 C11 C12 177.6(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C11 C10 C15 C14 0.9(4) . . . . ?
C9 C10 C15 C14 -177.8(3) . . . . ?
C13 C14 C15 C10 -0.6(5) . . . . ?
C2 N2 C16 C17 153.3(2) . . . . ?
C19 N2 C16 C17 23.1(3) . . . . ?
N2 C16 C17 C18 -31.6(4) . . . . ?
C16 C17 C18 C19 29.0(5) . . . . ?
C17 C18 C19 N2 -14.6(4) . . . . ?
C2 N2 C19 C18 -135.1(3) . . . . ?
C16 N2 C19 C18 -5.7(4) . . . . ?
N2 C2 C20 C21 -43.2(3) . . . . ?
C3 C2 C20 C21 80.5(3) . . . . ?
C1 C2 C20 C21 -167.9(2) . . . . ?
N2 C2 C20 C25 140.9(2) . . . . ?
C3 C2 C20 C25 -95.5(3) . . . . ?
C1 C2 C20 C25 16.1(3) . . . . ?
C25 C20 C21 O2 -178.9(2) . . . . ?
C2 C20 C21 O2 5.1(4) . . . . ?
C25 C20 C21 C22 1.5(4) . . . . ?
C2 C20 C21 C22 -174.5(2) . . . . ?
O2 C21 C22 C23 -180.0(2) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C21 C22 C23 O3 -177.0(3) . . . . ?
C26 O3 C23 C22 -173.8(3) . . . . ?
C26 O3 C23 C24 9.6(3) . . . . ?
C22 C23 C24 C25 0.8(4) . . . . ?
O3 C23 C24 C25 177.6(2) . . . . ?
C22 C23 C24 O4 -174.8(3) . . . . ?
O3 C23 C24 O4 2.0(3) . . . . ?
C26 O4 C24 C25 171.9(3) . . . . ?
C26 O4 C24 C23 -12.8(3) . . . . ?
C23 C24 C25 C20 0.3(4) . . . . ?
O4 C24 C25 C20 175.1(3) . . . . ?
C21 C20 C25 C24 -1.5(4) . . . . ?
C2 C20 C25 C24 174.6(2) . . . . ?
C24 O4 C26 O3 18.6(3) . . . . ?
C23 O3 C26 O4 -17.5(3) . . . . ?

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
C19 H19A O1 0.97 2.36 3.028(4) 125.4 . yes
C9 H9A O2 0.97 2.50 3.396(3) 153.9 2 yes
C5 H5 O3 0.93 2.61 3.398(4) 143.1 1_655 yes
O2 H2 N2 0.82 1.92 2.604(3) 140.0 . yes

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_exp_13319
_database_code_depnum_ccdc_archive 'CCDC 2348105'
loop_
_audit_author_name
_audit_author_address
WP-C
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-11-04 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 H28 N2 O5'
_chemical_formula_weight         532.57

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   9.8268(5)
_cell_length_b                   12.1370(6)
_cell_length_c                   12.7460(6)
_cell_angle_alpha                79.621(4)
_cell_angle_beta                 68.485(5)
_cell_angle_gamma                66.793(5)
_cell_volume                     1298.70(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    139(3)
_cell_measurement_reflns_used    4650
_cell_measurement_theta_min      3.9760
_cell_measurement_theta_max      70.6370

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_T_min  0.95523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      139(3)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8360
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.731
_diffrn_reflns_theta_max         67.244
_diffrn_reflns_theta_full        67.244
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4655
_reflns_number_gt                3932
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0941P)²+1.1048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4655
_refine_ls_number_parameters     426
_refine_ls_number_restraints     362
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1891
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.050
_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 0.7025(2) 0.25288(18) 0.49575(16) 0.0397(5) Uani 1 1 d . . . . .
O1 O 1.2138(3) 0.1747(3) 0.8150(2) 0.0793(7) Uani 1 1 d . . . . .
O2 O 1.4143(2) 0.0765(2) 0.6585(2) 0.0695(6) Uani 1 1 d . . . . .
O3 O 1.05674(19) 0.14241(17) 0.45628(15) 0.0506(5) Uani 1 1 d . . . . .
H3 H 1.115988 0.076093 0.427005 0.076 Uiso 1 1 calc R U . . .
O4 O 0.7644(2) 0.08395(15) 0.60916(15) 0.0470(4) Uani 1 1 d . . . . .
C1 C 1.3775(4) 0.1101(4) 0.7680(4) 0.0897(12) Uani 1 1 d . . . . .
H1A H 1.436482 0.160813 0.765907 0.108 Uiso 1 1 calc R U . . .
H1B H 1.409102 0.037506 0.816197 0.108 Uiso 1 1 calc R U . . .
C2 C 1.1537(4) 0.1735(3) 0.7324(3) 0.0551(7) Uani 1 1 d . . . . .
C3 C 1.2735(3) 0.1156(2) 0.6398(3) 0.0515(7) Uani 1 1 d . . . . .
C4 C 1.2477(3) 0.1044(2) 0.5456(2) 0.0483(6) Uani 1 1 d . . . . .
H4 H 1.331187 0.066821 0.481050 0.058 Uiso 1 1 calc R U . . .
C5 C 1.0913(3) 0.1513(2) 0.5484(2) 0.0436(6) Uani 1 1 d . . . . .
C6 C 0.9682(3) 0.2098(2) 0.6408(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 1.0001(3) 0.2227(2) 0.7355(2) 0.0497(6) Uani 1 1 d . . . . .
H7 H 0.918804 0.263741 0.799229 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8028(3) 0.2674(2) 0.6330(2) 0.0406(5) Uani 1 1 d . . . . .
C9 C 0.7853(2) 0.3759(2) 0.5529(2) 0.0407(5) Uani 1 1 d . . . . .
C10 C 0.8197(3) 0.4773(2) 0.5469(2) 0.0492(6) Uani 1 1 d . . . . .
H10 H 0.866067 0.485354 0.597353 0.059 Uiso 1 1 calc R U . . .
C11 C 0.7853(3) 0.5676(2) 0.4658(3) 0.0565(7) Uani 1 1 d . . . . .
H11 H 0.807945 0.637924 0.460918 0.068 Uiso 1 1 calc R U . . .
C12 C 0.7184(3) 0.5554(3) 0.3925(3) 0.0559(7) Uani 1 1 d . . . . .
H12 H 0.693577 0.618506 0.338790 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6866(3) 0.4528(2) 0.3956(2) 0.0476(6) Uani 1 1 d . . . . .
H13 H 0.642721 0.443872 0.343935 0.057 Uiso 1 1 calc R U . . .
C14 C 0.7212(2) 0.3646(2) 0.4766(2) 0.0403(5) Uani 1 1 d . . . . .
C15 C 0.7599(2) 0.1864(2) 0.5780(2) 0.0390(5) Uani 1 1 d . . . . .
C16 C 0.6328(3) 0.2128(3) 0.4335(2) 0.0498(6) Uani 1 1 d . . . . .
H16A H 0.528869 0.274533 0.437363 0.060 Uiso 1 1 calc R U . . .
H16B H 0.615837 0.138276 0.471296 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7290(4) 0.1891(2) 0.3113(2) 0.0532(7) Uani 1 1 d . . . . .
C18 C 0.6555(6) 0.2239(5) 0.2326(4) 0.127(2) Uani 1 1 d . . . . .
H18 H 0.545086 0.264095 0.254746 0.152 Uiso 1 1 calc R U . . .
C19 C 0.7418(9) 0.2005(6) 0.1197(5) 0.162(3) Uani 1 1 d . . . . .
H19 H 0.689195 0.225617 0.065357 0.194 Uiso 1 1 calc R U . . .
C20 C 0.9018(7) 0.1420(4) 0.0848(3) 0.1001(15) Uani 1 1 d . . . . .
H20 H 0.960619 0.127341 0.007388 0.120 Uiso 1 1 calc R U . . .
C21 C 0.9708(5) 0.1066(4) 0.1640(3) 0.0857(11) Uani 1 1 d . . . . .
H21 H 1.080993 0.065320 0.142555 0.103 Uiso 1 1 calc R U . . .
C22 C 0.8853(4) 0.1287(4) 0.2767(3) 0.0727(9) Uani 1 1 d . . . . .
H22 H 0.937990 0.100717 0.331060 0.087 Uiso 1 1 calc R U . . .
C23 C 0.6746(3) 0.2941(3) 0.7488(2) 0.0503(7) Uani 1 1 d . . . . .
C24 C 0.5717(3) 0.4099(3) 0.7787(3) 0.0663(8) Uani 1 1 d . . . . .
H24 H 0.584602 0.475227 0.727503 0.080 Uiso 1 1 calc R U . . .
C25 C 0.4524(5) 0.4325(5) 0.8797(3) 0.0953(14) Uani 1 1 d . . . . .
H25 H 0.385981 0.512809 0.898690 0.114 Uiso 0.621(5) 1 calc R U P A 1
C26 C 0.4284(6) 0.3395(6) 0.9535(4) 0.119(2) Uani 1 1 d D . . . .
C27 C 0.5326(6) 0.2205(5) 0.9280(3) 0.1057(17) Uani 1 1 d . . . . .
H27 H 0.519256 0.155711 0.979798 0.127 Uiso 0.379(5) 1 calc R U P A 2
C28 C 0.6553(4) 0.1999(4) 0.8259(3) 0.0706(9) Uani 1 1 d . . . . .
H28 H 0.726737 0.120404 0.808501 0.085 Uiso 1 1 calc R U . . .
N2 N 0.2879(10) 0.3777(7) 1.0462(6) 0.130(3) Uani 0.621(5) 1 d D U P A 1
C29 C 0.1942(11) 0.4951(8) 1.0829(7) 0.106(2) Uani 0.621(5) 1 d D U P A 1
H29A H 0.155293 0.547481 1.023023 0.127 Uiso 0.621(5) 1 calc R U P A 1
H29B H 0.252724 0.530897 1.106391 0.127 Uiso 0.621(5) 1 calc R U P A 1
C30 C 0.0611(9) 0.4756(8) 1.1823(6) 0.109(2) Uani 0.621(5) 1 d D U P A 1
H30A H 0.027240 0.531298 1.242526 0.131 Uiso 0.621(5) 1 calc R U P A 1
H30B H -0.029714 0.488592 1.158683 0.131 Uiso 0.621(5) 1 calc R U P A 1
C31 C 0.1243(13) 0.3503(9) 1.2223(7) 0.134(3) Uani 0.621(5) 1 d D U P A 1
H31A H 0.039727 0.317215 1.258640 0.161 Uiso 0.621(5) 1 calc R U P A 1
H31B H 0.176590 0.344563 1.277404 0.161 Uiso 0.621(5) 1 calc R U P A 1
C32 C 0.2415(11) 0.2832(8) 1.1171(7) 0.120(3) Uani 0.621(5) 1 d D U P A 1
H32 H 0.184947 0.268045 1.073226 0.144 Uiso 0.621(5) 1 d R U P A 1
C33 C 0.5000(13) 0.1343(8) 1.0076(6) 0.128(3) Uani 0.621(5) 1 d . U P A 1
H33A H 0.594476 0.081393 1.027362 0.154 Uiso 0.621(5) 1 d R U P A 1
H33B H 0.470337 0.083789 0.973475 0.154 Uiso 0.621(5) 1 d R U P A 1
O5 O 0.3749(11) 0.1792(10) 1.0996(8) 0.224(6) Uani 0.621(5) 1 d D . P A 1
N2' N 0.3496(13) 0.3241(14) 1.0702(8) 0.139(4) Uani 0.379(5) 1 d D U P A 2
C29' C 0.2028(17) 0.4217(13) 1.0894(14) 0.152(5) Uani 0.379(5) 1 d D U P A 2
H29' H 0.223650 0.456759 1.144544 0.182 Uiso 0.379(5) 1 calc R U P A 2
C30' C 0.0881(13) 0.3751(17) 1.1826(13) 0.152(5) Uani 0.379(5) 1 d D U P A 2
H30C H 0.045096 0.330970 1.152740 0.183 Uiso 0.379(5) 1 calc R U P A 2
H30D H 0.000988 0.440406 1.229651 0.183 Uiso 0.379(5) 1 calc R U P A 2
C31' C 0.1970(18) 0.2914(15) 1.2473(8) 0.164(5) Uani 0.379(5) 1 d D U P A 2
H31C H 0.228193 0.336268 1.286369 0.197 Uiso 0.379(5) 1 calc R U P A 2
H31D H 0.149869 0.236781 1.302244 0.197 Uiso 0.379(5) 1 calc R U P A 2
C32' C 0.3316(19) 0.2257(11) 1.1488(11) 0.125(4) Uani 0.379(5) 1 d D U P A 2
H32A H 0.427291 0.180354 1.169583 0.150 Uiso 0.379(5) 1 calc R U P A 2
H32B H 0.304866 0.170224 1.118348 0.150 Uiso 0.379(5) 1 calc R U P A 2
C33' C 0.3274(13) 0.5363(11) 0.9265(9) 0.111(4) Uani 0.379(5) 1 d D U P A 2
H33C H 0.293709 0.585921 0.863584 0.133 Uiso 0.379(5) 1 d R U P A 2
H33D H 0.371437 0.581108 0.954608 0.133 Uiso 0.379(5) 1 d R U P A 2
O5' O 0.1988(12) 0.5228(10) 1.0159(9) 0.168(6) Uani 0.379(5) 1 d D . P A 2


_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 C15 1.356(3) . ?
N1 C14 1.406(3) . ?
N1 C16 1.462(3) . ?
O1 C2 1.387(3) . ?
O1 C1 1.424(5) . ?
O2 C3 1.372(3) . ?
O2 C1 1.400(5) . ?
O3 C5 1.368(3) . ?
O3 H3 0.8400 . ?
O4 C15 1.224(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.376(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.354(4) . ?
C4 C5 1.402(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C6 C7 1.401(4) . ?
C6 C8 1.529(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.508(3) . ?
C8 C23 1.536(3) . ?
C8 C15 1.558(3) . ?
C9 C10 1.382(4) . ?
C9 C14 1.388(3) . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9500 . ?
C16 C17 1.506(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.351(4) . ?
C17 C18 1.358(5) . ?
C18 C19 1.391(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.334(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.390(4) . ?
C23 C28 1.392(5) . ?
C24 C25 1.369(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.371(7) . ?
C25 C33' 1.402(11) . ?
C25 H25 0.9500 . ?
C26 C27 1.413(8) . ?
C26 N2 1.419(6) . ?
C26 N2' 1.420(8) . ?
C27 C33 1.368(9) . ?
C27 C28 1.393(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N2 C29 1.409(8) . ?
N2 C32 1.442(8) . ?
C29 C30 1.514(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.472(9) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.520(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 O5 1.394(9) . ?
C32 H32 1.0000 . ?
C33 O5 1.352(12) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
N2' C29' 1.429(8) . ?
N2' C32' 1.437(9) . ?
C29' O5' 1.399(9) . ?
C29' C30' 1.510(9) . ?
C29' H29' 1.0000 . ?
C30' C31' 1.532(10) . ?
C30' H30C 0.9900 . ?
C30' H30D 0.9900 . ?
C31' C32' 1.508(9) . ?
C31' H31C 0.9900 . ?
C31' H31D 0.9900 . ?
C32' H32A 0.9900 . ?
C32' H32B 0.9900 . ?
C33' O5' 1.401(9) . ?
C33' H33C 0.9900 . ?
C33' H33D 0.9900 . ?

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
C15 N1 C14 111.3(2) . . ?
C15 N1 C16 124.4(2) . . ?
C14 N1 C16 124.3(2) . . ?
C2 O1 C1 103.9(3) . . ?
C3 O2 C1 105.2(3) . . ?
C5 O3 H3 109.5 . . ?
O2 C1 O1 110.7(3) . . ?
O2 C1 H1A 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C7 C2 C3 122.1(3) . . ?
C7 C2 O1 127.9(3) . . ?
C3 C2 O1 110.0(3) . . ?
C4 C3 O2 127.6(3) . . ?
C4 C3 C2 122.2(2) . . ?
O2 C3 C2 110.1(3) . . ?
C3 C4 C5 116.4(3) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
O3 C5 C6 117.9(2) . . ?
O3 C5 C4 119.5(2) . . ?
C6 C5 C4 122.6(2) . . ?
C5 C6 C7 119.3(2) . . ?
C5 C6 C8 119.1(2) . . ?
C7 C6 C8 121.4(2) . . ?
C2 C7 C6 117.3(3) . . ?
C2 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C9 C8 C6 112.3(2) . . ?
C9 C8 C23 112.1(2) . . ?
C6 C8 C23 113.0(2) . . ?
C9 C8 C15 100.85(19) . . ?
C6 C8 C15 113.35(19) . . ?
C23 C8 C15 104.43(19) . . ?
C10 C9 C14 119.6(2) . . ?
C10 C9 C8 131.0(2) . . ?
C14 C9 C8 109.4(2) . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.5(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C13 C14 C9 122.2(2) . . ?
C13 C14 N1 128.2(2) . . ?
C9 C14 N1 109.5(2) . . ?
O4 C15 N1 125.3(2) . . ?
O4 C15 C8 126.3(2) . . ?
N1 C15 C8 108.1(2) . . ?
N1 C16 C17 114.6(2) . . ?
N1 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
N1 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C22 C17 C18 118.0(3) . . ?
C22 C17 C16 122.8(3) . . ?
C18 C17 C16 119.1(3) . . ?
C17 C18 C19 120.0(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 121.6(4) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C21 C20 C19 117.3(4) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C20 C21 C22 121.4(4) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C17 C22 C21 121.7(3) . . ?
C17 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C24 C23 C28 118.1(3) . . ?
C24 C23 C8 122.2(3) . . ?
C28 C23 C8 119.7(3) . . ?
C25 C24 C23 121.9(4) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C24 C25 C26 120.1(4) . . ?
C24 C25 C33' 133.6(7) . . ?
C26 C25 C33' 105.9(6) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 N2 112.5(6) . . ?
C27 C26 N2 127.5(6) . . ?
C25 C26 N2' 137.0(8) . . ?
C27 C26 N2' 100.5(7) . . ?
C33 C27 C28 125.6(6) . . ?
C33 C27 C26 115.4(6) . . ?
C28 C27 C26 118.9(4) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C23 C28 C27 121.0(4) . . ?
C23 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C29 N2 C26 128.6(6) . . ?
C29 N2 C32 115.7(6) . . ?
C26 N2 C32 115.5(6) . . ?
N2 C29 C30 102.6(7) . . ?
N2 C29 H29A 111.3 . . ?
C30 C29 H29A 111.3 . . ?
N2 C29 H29B 111.3 . . ?
C30 C29 H29B 111.3 . . ?
H29A C29 H29B 109.2 . . ?
C31 C30 C29 105.5(7) . . ?
C31 C30 H30A 110.6 . . ?
C29 C30 H30A 110.6 . . ?
C31 C30 H30B 110.6 . . ?
C29 C30 H30B 110.6 . . ?
H30A C30 H30B 108.8 . . ?
C30 C31 C32 105.1(7) . . ?
C30 C31 H31A 110.7 . . ?
C32 C31 H31A 110.7 . . ?
C30 C31 H31B 110.7 . . ?
C32 C31 H31B 110.7 . . ?
H31A C31 H31B 108.8 . . ?
O5 C32 N2 107.2(7) . . ?
O5 C32 C31 132.9(10) . . ?
N2 C32 C31 101.2(7) . . ?
O5 C32 H32 101.6 . . ?
N2 C32 H32 99.5 . . ?
C31 C32 H32 110.0 . . ?
O5 C33 C27 113.4(8) . . ?
O5 C33 H33A 112.4 . . ?
C27 C33 H33A 110.7 . . ?
O5 C33 H33B 105.3 . . ?
C27 C33 H33B 107.4 . . ?
H33A C33 H33B 107.2 . . ?
C33 O5 C32 133.3(8) . . ?
C26 N2' C29' 103.0(9) . . ?
C26 N2' C32' 137.0(12) . . ?
C29' N2' C32' 110.0(6) . . ?
O5' C29' N2' 117.2(10) . . ?
O5' C29' C30' 137.9(11) . . ?
N2' C29' C30' 104.5(6) . . ?
O5' C29' H29' 92.0 . . ?
N2' C29' H29' 92.0 . . ?
C30' C29' H29' 92.0 . . ?
C29' C30' C31' 99.6(7) . . ?
C29' C30' H30C 111.9 . . ?
C31' C30' H30C 111.9 . . ?
C29' C30' H30D 111.9 . . ?
C31' C30' H30D 111.9 . . ?
H30C C30' H30D 109.6 . . ?
C32' C31' C30' 98.5(7) . . ?
C32' C31' H31C 112.1 . . ?
C30' C31' H31C 112.1 . . ?
C32' C31' H31D 112.1 . . ?
C30' C31' H31D 112.1 . . ?
H31C C31' H31D 109.7 . . ?
N2' C32' C31' 101.0(7) . . ?
N2' C32' H32A 111.6 . . ?
C31' C32' H32A 111.6 . . ?
N2' C32' H32B 111.6 . . ?
C31' C32' H32B 111.6 . . ?
H32A C32' H32B 109.4 . . ?
O5' C33' C25 118.2(10) . . ?
O5' C33' H33C 110.8 . . ?
C25 C33' H33C 106.9 . . ?
O5' C33' H33D 107.2 . . ?
C25 C33' H33D 106.4 . . ?
H33C C33' H33D 106.7 . . ?
C29' O5' C33' 125.2(11) . . ?

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.049



