# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc29cs6p
_database_code_depnum_ccdc_archive 'CCDC 2126482'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.molstruc.2023.135539 2023
loop_
_audit_author_name
_audit_author_address
'Necmi Dege'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2024-04-02 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            'C32 H26 N2 O3'
_chemical_formula_weight         486.55

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      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                   8.1861(11)
_cell_length_b                   11.0003(16)
_cell_length_c                   14.636(2)
_cell_angle_alpha                76.208(5)
_cell_angle_beta                 78.404(4)
_cell_angle_gamma                86.588(4)
_cell_volume                     1253.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39117
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4929
_reflns_number_gt                2714
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (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)+(0.0480P)²+0.0425P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0178(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4929
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O2 O 0.26064(16) 0.31396(13) 0.65041(10) 0.0439(4) Uani 1 1 d . . . . .
O3 O 0.11432(17) 0.35423(13) 0.92539(10) 0.0434(4) Uani 1 1 d . . . . .
O1 O 0.45961(18) 0.34216(14) 0.98289(11) 0.0503(4) Uani 1 1 d . . . . .
N1 N 0.4364(2) 0.53464(18) 0.88122(14) 0.0404(5) Uani 1 1 d . . . . .
N2 N 0.6270(2) 0.28559(17) 0.80129(16) 0.0440(5) Uani 1 1 d . . . . .
C10 C 0.2291(2) 0.33477(18) 0.73049(15) 0.0346(5) Uani 1 1 d . . . . .
C9 C 0.3260(2) 0.27238(17) 0.80840(13) 0.0316(5) Uani 1 1 d . . . . .
C1 C 0.4617(2) 0.5829(2) 0.78133(15) 0.0355(5) Uani 1 1 d . . . . .
C6 C 0.4884(2) 0.48503(19) 0.73516(14) 0.0348(5) Uani 1 1 d . . . . .
C11 C 0.0952(2) 0.42252(19) 0.75795(15) 0.0366(5) Uani 1 1 d . . . . .
C18 C 0.4215(2) 0.15233(17) 0.78823(14) 0.0345(5) Uani 1 1 d . . . . .
H18 H 0.456907 0.166730 0.718492 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3193(2) 0.03412(18) 0.82031(15) 0.0364(5) Uani 1 1 d . . . . .
C8 C 0.4530(2) 0.4081(2) 0.90312(16) 0.0371(5) Uani 1 1 d . . . . .
C25 C 0.5796(2) 0.15364(19) 0.82888(15) 0.0390(5) Uani 1 1 d . . . . .
H25 H 0.549414 0.129132 0.898972 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4743(2) 0.36233(18) 0.80927(14) 0.0342(5) Uani 1 1 d . . . . .
C16 C 0.0462(2) 0.42948(19) 0.85336(16) 0.0386(5) Uani 1 1 d . . . . .
C17 C 0.1980(2) 0.24373(18) 0.90224(14) 0.0397(5) Uani 1 1 d . . . . .
H17A H 0.115769 0.186866 0.897258 0.048 Uiso 1 1 calc R U . . .
H17B H 0.253844 0.201936 0.953917 0.048 Uiso 1 1 calc R U . . .
C20 C 0.2217(3) 0.0057(2) 0.76120(16) 0.0443(6) Uani 1 1 d . . . . .
H20 H 0.223989 0.057298 0.700554 0.053 Uiso 1 1 calc R U . . .
C27 C 0.7794(3) 0.0929(2) 0.68919(17) 0.0437(6) Uani 1 1 d . . . . .
C2 C 0.4669(3) 0.7064(2) 0.73219(17) 0.0471(6) Uani 1 1 d . . . . .
H2A H 0.447153 0.771090 0.764095 0.057 Uiso 1 1 calc R U . . .
C12 C 0.0203(3) 0.5044(2) 0.68935(17) 0.0487(6) Uani 1 1 d . . . . .
H12 H 0.050636 0.500491 0.625371 0.058 Uiso 1 1 calc R U . . .
C26 C 0.7225(3) 0.0681(2) 0.79597(16) 0.0492(6) Uani 1 1 d . . . . .
H26A H 0.816433 0.078073 0.824605 0.059 Uiso 1 1 calc R U . . .
H26B H 0.686895 -0.018165 0.819643 0.059 Uiso 1 1 calc R U . . .
C24 C 0.3161(3) -0.0481(2) 0.90880(16) 0.0507(6) Uani 1 1 d . . . . .
H24 H 0.382581 -0.032447 0.949242 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5279(3) 0.5109(2) 0.63662(16) 0.0482(6) Uani 1 1 d . . . . .
H5 H 0.549704 0.446308 0.604713 0.058 Uiso 1 1 calc R U . . .
C15 C -0.0743(3) 0.5159(2) 0.87965(18) 0.0496(6) Uani 1 1 d . . . . .
H15 H -0.107412 0.519471 0.943586 0.060 Uiso 1 1 calc R U . . .
C21 C 0.1210(3) -0.0986(2) 0.79135(19) 0.0546(7) Uani 1 1 d . . . . .
H21 H 0.054441 -0.115315 0.751333 0.066 Uiso 1 1 calc R U . . .
C3 C 0.5027(3) 0.7299(2) 0.63315(19) 0.0593(7) Uani 1 1 d . . . . .
H3 H 0.505364 0.812375 0.597835 0.071 Uiso 1 1 calc R U . . .
C22 C 0.1183(3) -0.1774(2) 0.8796(2) 0.0587(7) Uani 1 1 d . . . . .
H22 H 0.050278 -0.247300 0.899455 0.070 Uiso 1 1 calc R U . . .
C32 C 0.8958(3) 0.1838(2) 0.6413(2) 0.0602(7) Uani 1 1 d . . . . .
H32 H 0.944249 0.226740 0.676416 0.072 Uiso 1 1 calc R U . . .
C23 C 0.2161(3) -0.1528(2) 0.93814(18) 0.0583(7) Uani 1 1 d . . . . .
H23 H 0.215532 -0.206474 0.997854 0.070 Uiso 1 1 calc R U . . .
C28 C 0.7134(3) 0.0293(2) 0.6345(2) 0.0642(7) Uani 1 1 d . . . . .
H28 H 0.636171 -0.033397 0.664518 0.077 Uiso 1 1 calc R U . . .
C14 C -0.1433(3) 0.5955(2) 0.8101(2) 0.0564(7) Uani 1 1 d . . . . .
H14 H -0.222731 0.654308 0.827179 0.068 Uiso 1 1 calc R U . . .
C13 C -0.0973(3) 0.5904(2) 0.7147(2) 0.0585(7) Uani 1 1 d . . . . .
H13 H -0.145791 0.644954 0.668269 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5346(3) 0.6350(2) 0.58541(17) 0.0584(7) Uani 1 1 d . . . . .
H4 H 0.560787 0.653798 0.518773 0.070 Uiso 1 1 calc R U . . .
C31 C 0.9418(4) 0.2123(3) 0.5434(2) 0.0802(8) Uani 1 1 d . . . . .
H31 H 1.019251 0.274735 0.512963 0.096 Uiso 1 1 calc R U . . .
C29 C 0.7604(4) 0.0573(3) 0.5360(2) 0.0867(9) Uani 1 1 d . . . . .
H29 H 0.714641 0.013796 0.500207 0.104 Uiso 1 1 calc R U . . .
C30 C 0.8748(4) 0.1496(3) 0.4908(2) 0.0921(10) Uani 1 1 d . . . . .
H30 H 0.906033 0.168935 0.424319 0.110 Uiso 1 1 calc R U . . .
H1 H 0.444(3) 0.580(2) 0.9193(18) 0.073(9) Uiso 1 1 d . . . . .
H2 H 0.673(3) 0.304(2) 0.7445(18) 0.072(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C10 1.221(2) . ?
O3 C16 1.368(2) . ?
O3 C17 1.437(2) . ?
O1 C8 1.229(2) . ?
N1 C8 1.357(3) . ?
N1 C1 1.408(3) . ?
N1 H1 0.84(2) . ?
N2 C25 1.465(3) . ?
N2 C7 1.467(3) . ?
N2 H2 0.82(2) . ?
C10 C11 1.476(3) . ?
C10 C9 1.525(3) . ?
C9 C17 1.529(3) . ?
C9 C18 1.553(3) . ?
C9 C7 1.615(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.387(3) . ?
C6 C5 1.376(3) . ?
C6 C7 1.510(3) . ?
C11 C16 1.392(3) . ?
C11 C12 1.395(3) . ?
C18 C19 1.514(3) . ?
C18 C25 1.531(3) . ?
C18 H18 0.9800 . ?
C19 C20 1.386(3) . ?
C19 C24 1.388(3) . ?
C8 C7 1.547(3) . ?
C25 C26 1.531(3) . ?
C25 H25 0.9800 . ?
C16 C15 1.391(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C27 C28 1.382(3) . ?
C27 C32 1.382(3) . ?
C27 C26 1.501(3) . ?
C2 C3 1.383(3) . ?
C2 H2A 0.9300 . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C24 C23 1.385(3) . ?
C24 H24 0.9300 . ?
C5 C4 1.390(3) . ?
C5 H5 0.9300 . ?
C15 C14 1.368(3) . ?
C15 H15 0.9300 . ?
C21 C22 1.370(3) . ?
C21 H21 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C22 C23 1.364(3) . ?
C22 H22 0.9300 . ?
C32 C31 1.369(3) . ?
C32 H32 0.9300 . ?
C23 H23 0.9300 . ?
C28 C29 1.377(4) . ?
C28 H28 0.9300 . ?
C14 C13 1.385(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C31 C30 1.356(4) . ?
C31 H31 0.9300 . ?
C29 C30 1.374(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

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
C16 O3 C17 114.81(15) . . ?
C8 N1 C1 111.28(19) . . ?
C8 N1 H1 123.5(17) . . ?
C1 N1 H1 122.0(17) . . ?
C25 N2 C7 108.28(16) . . ?
C25 N2 H2 110.2(18) . . ?
C7 N2 H2 106.2(17) . . ?
O2 C10 C11 122.08(19) . . ?
O2 C10 C9 122.27(18) . . ?
C11 C10 C9 115.65(18) . . ?
C10 C9 C17 106.13(16) . . ?
C10 C9 C18 112.78(16) . . ?
C17 C9 C18 111.57(16) . . ?
C10 C9 C7 109.99(15) . . ?
C17 C9 C7 113.77(15) . . ?
C18 C9 C7 102.77(14) . . ?
C2 C1 C6 122.5(2) . . ?
C2 C1 N1 128.0(2) . . ?
C6 C1 N1 109.51(19) . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 131.32(19) . . ?
C1 C6 C7 109.15(17) . . ?
C16 C11 C12 118.32(19) . . ?
C16 C11 C10 120.24(19) . . ?
C12 C11 C10 121.4(2) . . ?
C19 C18 C25 117.89(17) . . ?
C19 C18 C9 115.06(16) . . ?
C25 C18 C9 103.24(15) . . ?
C19 C18 H18 106.6 . . ?
C25 C18 H18 106.6 . . ?
C9 C18 H18 106.6 . . ?
C20 C19 C24 117.5(2) . . ?
C20 C19 C18 120.02(19) . . ?
C24 C19 C18 122.50(19) . . ?
O1 C8 N1 125.74(19) . . ?
O1 C8 C7 125.90(19) . . ?
N1 C8 C7 108.24(19) . . ?
N2 C25 C26 112.18(17) . . ?
N2 C25 C18 103.96(16) . . ?
C26 C25 C18 115.83(17) . . ?
N2 C25 H25 108.2 . . ?
C26 C25 H25 108.2 . . ?
C18 C25 H25 108.2 . . ?
N2 C7 C6 113.07(16) . . ?
N2 C7 C8 107.91(16) . . ?
C6 C7 C8 101.33(16) . . ?
N2 C7 C9 105.63(15) . . ?
C6 C7 C9 115.50(15) . . ?
C8 C7 C9 113.37(15) . . ?
O3 C16 C15 116.7(2) . . ?
O3 C16 C11 122.47(18) . . ?
C15 C16 C11 120.9(2) . . ?
O3 C17 C9 112.73(16) . . ?
O3 C17 H17A 109.0 . . ?
C9 C17 H17A 109.0 . . ?
O3 C17 H17B 109.0 . . ?
C9 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C28 C27 C32 117.3(2) . . ?
C28 C27 C26 121.5(2) . . ?
C32 C27 C26 121.1(2) . . ?
C1 C2 C3 116.9(2) . . ?
C1 C2 H2A 121.5 . . ?
C3 C2 H2A 121.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C27 C26 C25 114.14(18) . . ?
C27 C26 H26A 108.7 . . ?
C25 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C23 C24 C19 121.4(2) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C31 C32 C27 121.7(2) . . ?
C31 C32 H32 119.1 . . ?
C27 C32 H32 119.1 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C29 C28 C27 121.0(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C31 C30 C29 119.7(3) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?

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
O2 C10 C9 C17 -141.67(18) . . . . ?
C11 C10 C9 C17 38.6(2) . . . . ?
O2 C10 C9 C18 -19.2(2) . . . . ?
C11 C10 C9 C18 161.05(16) . . . . ?
O2 C10 C9 C7 94.8(2) . . . . ?
C11 C10 C9 C7 -84.89(19) . . . . ?
C8 N1 C1 C2 -174.91(19) . . . . ?
C8 N1 C1 C6 2.9(2) . . . . ?
C2 C1 C6 C5 2.5(3) . . . . ?
N1 C1 C6 C5 -175.36(17) . . . . ?
C2 C1 C6 C7 179.94(17) . . . . ?
N1 C1 C6 C7 2.0(2) . . . . ?
O2 C10 C11 C16 170.19(18) . . . . ?
C9 C10 C11 C16 -10.1(3) . . . . ?
O2 C10 C11 C12 -13.0(3) . . . . ?
C9 C10 C11 C12 166.77(17) . . . . ?
C10 C9 C18 C19 -84.4(2) . . . . ?
C17 C9 C18 C19 35.0(2) . . . . ?
C7 C9 C18 C19 157.25(16) . . . . ?
C10 C9 C18 C25 145.79(16) . . . . ?
C17 C9 C18 C25 -94.86(18) . . . . ?
C7 C9 C18 C25 27.42(18) . . . . ?
C25 C18 C19 C20 -153.13(19) . . . . ?
C9 C18 C19 C20 84.6(2) . . . . ?
C25 C18 C19 C24 28.0(3) . . . . ?
C9 C18 C19 C24 -94.2(2) . . . . ?
C1 N1 C8 O1 169.85(19) . . . . ?
C1 N1 C8 C7 -6.3(2) . . . . ?
C7 N2 C25 C26 163.43(17) . . . . ?
C7 N2 C25 C18 37.5(2) . . . . ?
C19 C18 C25 N2 -168.18(17) . . . . ?
C9 C18 C25 N2 -40.1(2) . . . . ?
C19 C18 C25 C26 68.3(2) . . . . ?
C9 C18 C25 C26 -163.63(17) . . . . ?
C25 N2 C7 C6 -146.51(17) . . . . ?
C25 N2 C7 C8 102.27(19) . . . . ?
C25 N2 C7 C9 -19.3(2) . . . . ?
C5 C6 C7 N2 56.4(3) . . . . ?
C1 C6 C7 N2 -120.57(18) . . . . ?
C5 C6 C7 C8 171.6(2) . . . . ?
C1 C6 C7 C8 -5.34(19) . . . . ?
C5 C6 C7 C9 -65.4(3) . . . . ?
C1 C6 C7 C9 117.60(18) . . . . ?
O1 C8 C7 N2 -50.2(3) . . . . ?
N1 C8 C7 N2 126.00(18) . . . . ?
O1 C8 C7 C6 -169.19(19) . . . . ?
N1 C8 C7 C6 7.00(19) . . . . ?
O1 C8 C7 C9 66.4(2) . . . . ?
N1 C8 C7 C9 -117.39(18) . . . . ?
C10 C9 C7 N2 -126.28(18) . . . . ?
C17 C9 C7 N2 114.82(19) . . . . ?
C18 C9 C7 N2 -5.96(19) . . . . ?
C10 C9 C7 C6 -0.5(2) . . . . ?
C17 C9 C7 C6 -119.44(18) . . . . ?
C18 C9 C7 C6 119.78(17) . . . . ?
C10 C9 C7 C8 115.77(19) . . . . ?
C17 C9 C7 C8 -3.1(2) . . . . ?
C18 C9 C7 C8 -123.91(17) . . . . ?
C17 O3 C16 C15 162.09(17) . . . . ?
C17 O3 C16 C11 -18.8(3) . . . . ?
C12 C11 C16 O3 -179.09(17) . . . . ?
C10 C11 C16 O3 -2.2(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C10 C11 C16 C15 176.92(18) . . . . ?
C16 O3 C17 C9 51.7(2) . . . . ?
C10 C9 C17 O3 -60.1(2) . . . . ?
C18 C9 C17 O3 176.72(15) . . . . ?
C7 C9 C17 O3 61.0(2) . . . . ?
C24 C19 C20 C21 2.2(3) . . . . ?
C18 C19 C20 C21 -176.70(18) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
N1 C1 C2 C3 176.56(19) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
C10 C11 C12 C13 -176.26(19) . . . . ?
C28 C27 C26 C25 -92.3(3) . . . . ?
C32 C27 C26 C25 85.4(2) . . . . ?
N2 C25 C26 C27 -62.2(2) . . . . ?
C18 C25 C26 C27 57.0(2) . . . . ?
C20 C19 C24 C23 -1.7(3) . . . . ?
C18 C19 C24 C23 177.22(19) . . . . ?
C1 C6 C5 C4 -2.1(3) . . . . ?
C7 C6 C5 C4 -178.85(19) . . . . ?
O3 C16 C15 C14 178.37(18) . . . . ?
C11 C16 C15 C14 -0.7(3) . . . . ?
C19 C20 C21 C22 -1.4(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C28 C27 C32 C31 1.5(3) . . . . ?
C26 C27 C32 C31 -176.3(2) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C19 C24 C23 C22 0.3(4) . . . . ?
C32 C27 C28 C29 -1.1(4) . . . . ?
C26 C27 C28 C29 176.7(2) . . . . ?
C16 C15 C14 C13 0.9(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C15 C14 C13 C12 -0.3(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C27 C32 C31 C30 -1.0(4) . . . . ?
C27 C28 C29 C30 0.2(4) . . . . ?
C32 C31 C30 C29 0.0(5) . . . . ?
C28 C29 C30 C31 0.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C17 H17B O1 0.97 2.51 3.009(2) 111.8 . yes
C15 H15 O3 0.93 2.61 3.436(3) 147.7 2_567 yes
N1 H1 O1 0.84(2) 2.13(2) 2.936(3) 160(2) 2_667 yes

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc29csvb
_database_code_depnum_ccdc_archive 'CCDC 2126502'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.molstruc.2023.135539 2023
loop_
_audit_author_name
_audit_author_address
'Necmi Dege'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2024-04-02 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 O4'
_chemical_formula_weight         516.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   10.392(2)
_cell_length_b                   11.038(2)
_cell_length_c                   13.930(3)
_cell_angle_alpha                66.842(6)
_cell_angle_beta                 83.821(8)
_cell_angle_gamma                68.789(6)
_cell_volume                     1368.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54373
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6273
_reflns_number_gt                4521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (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)+(0.0491P)²+0.3855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6273
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.89640(11) 0.38131(11) 0.05419(7) 0.0383(3) Uani 1 1 d . . . . .
O2 O 0.66279(11) 0.58023(11) 0.15359(8) 0.0404(3) Uani 1 1 d . . . . .
O3 O 0.68592(14) 0.28069(13) 0.44671(9) 0.0520(3) Uani 1 1 d . . . . .
O4 O 0.22963(11) 0.16452(14) 0.15919(10) 0.0525(3) Uani 1 1 d . . . . .
N2 N 0.95595(13) 0.15111(12) 0.27285(9) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.99444(13) 0.47007(14) 0.13868(10) 0.0347(3) Uani 1 1 d . . . . .
C9 C 0.85734(14) 0.10950(14) 0.23770(11) 0.0280(3) Uani 1 1 d . . . . .
H9 H 0.849819 0.147781 0.161186 0.034 Uiso 1 1 calc R U . . .
C17 C 0.72442(14) 0.18373(15) 0.28178(11) 0.0281(3) Uani 1 1 d . . . . .
H17 H 0.731937 0.130643 0.357494 0.034 Uiso 1 1 calc R U . . .
C26 C 0.73561(14) 0.32823(14) 0.26452(10) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.96975(14) 0.34547(15) 0.31040(11) 0.0294(3) Uani 1 1 d . . . . .
C27 C 0.69040(15) 0.36724(16) 0.36028(12) 0.0338(3) Uani 1 1 d . . . . .
C18 C 0.59179(14) 0.18653(15) 0.24378(11) 0.0304(3) Uani 1 1 d . . . . .
C2 C 0.89648(14) 0.30252(14) 0.24786(10) 0.0264(3) Uani 1 1 d . . . . .
C25 C 0.64246(15) 0.45042(15) 0.17369(12) 0.0338(3) Uani 1 1 d . . . . .
H25A H 0.661559 0.428934 0.111339 0.041 Uiso 1 1 calc R U . . .
H25B H 0.546686 0.461387 0.189632 0.041 Uiso 1 1 calc R U . . .
C11 C 1.03037(15) -0.11923(15) 0.23646(12) 0.0334(3) Uani 1 1 d . . . . .
C8 C 1.02443(15) 0.44437(15) 0.24238(11) 0.0329(3) Uani 1 1 d . . . . .
C1 C 0.92573(14) 0.38966(15) 0.13419(11) 0.0299(3) Uani 1 1 d . . . . .
C33 C 0.64961(15) 0.61586(17) 0.23866(13) 0.0383(4) Uani 1 1 d . . . . .
C10 C 0.89858(15) -0.04998(15) 0.28087(13) 0.0365(4) Uani 1 1 d . . . . .
H10A H 0.910470 -0.086290 0.356301 0.044 Uiso 1 1 calc R U . . .
H10B H 0.824724 -0.074039 0.264802 0.044 Uiso 1 1 calc R U . . .
C28 C 0.65491(15) 0.51779(17) 0.34041(13) 0.0370(4) Uani 1 1 d . . . . .
C4 C 0.99519(17) 0.29663(18) 0.41648(12) 0.0405(4) Uani 1 1 d . . . . .
H4 H 0.962396 0.227705 0.462733 0.049 Uiso 1 1 calc R U . . .
C21 C 0.34914(15) 0.17568(17) 0.18173(13) 0.0382(4) Uani 1 1 d . . . . .
C23 C 0.48650(16) 0.16760(18) 0.31281(13) 0.0405(4) Uani 1 1 d . . . . .
H23 H 0.497173 0.157928 0.381178 0.049 Uiso 1 1 calc R U . . .
C29 C 0.63385(18) 0.5639(2) 0.42290(15) 0.0490(4) Uani 1 1 d . . . . .
H29 H 0.636007 0.500188 0.491091 0.059 Uiso 1 1 calc R U . . .
C12 C 1.02965(18) -0.12599(17) 0.13913(13) 0.0452(4) Uani 1 1 d . . . . .
H12 H 0.946101 -0.091008 0.102203 0.054 Uiso 1 1 calc R U . . .
C19 C 0.56940(16) 0.20237(19) 0.14308(13) 0.0435(4) Uani 1 1 d . . . . .
H19 H 0.636752 0.217062 0.094710 0.052 Uiso 1 1 calc R U . . .
C16 C 1.15667(17) -0.17333(18) 0.28942(14) 0.0452(4) Uani 1 1 d . . . . .
H16 H 1.160166 -0.170409 0.354874 0.054 Uiso 1 1 calc R U . . .
C22 C 0.36704(16) 0.1628(2) 0.28238(14) 0.0464(4) Uani 1 1 d . . . . .
H22 H 0.298244 0.150934 0.329941 0.056 Uiso 1 1 calc R U . . .
C32 C 0.62843(18) 0.75528(18) 0.22008(17) 0.0510(5) Uani 1 1 d . . . . .
H32 H 0.627721 0.819528 0.152328 0.061 Uiso 1 1 calc R U . . .
C20 C 0.45029(17) 0.19722(19) 0.11118(13) 0.0450(4) Uani 1 1 d . . . . .
H20 H 0.438661 0.208221 0.042604 0.054 Uiso 1 1 calc R U . . .
C30 C 0.6099(2) 0.7025(2) 0.40452(19) 0.0611(6) Uani 1 1 d . . . . .
H30 H 0.594828 0.732410 0.459867 0.073 Uiso 1 1 calc R U . . .
C7 C 1.0998(2) 0.49987(18) 0.27772(14) 0.0498(4) Uani 1 1 d . . . . .
H7 H 1.134991 0.566737 0.231436 0.060 Uiso 1 1 calc R U . . .
C5 C 1.0705(2) 0.3520(2) 0.45316(14) 0.0545(5) Uani 1 1 d . . . . .
H5 H 1.087140 0.321055 0.524647 0.065 Uiso 1 1 calc R U . . .
C31 C 0.60855(19) 0.7968(2) 0.3033(2) 0.0610(6) Uani 1 1 d . . . . .
H31 H 0.593919 0.889946 0.291241 0.073 Uiso 1 1 calc R U . . .
C15 C 1.27738(19) -0.2315(2) 0.24635(17) 0.0577(5) Uani 1 1 d . . . . .
H15 H 1.361158 -0.267921 0.283287 0.069 Uiso 1 1 calc R U . . .
C14 C 1.2751(2) -0.2362(2) 0.14990(17) 0.0595(5) Uani 1 1 d . . . . .
H14 H 1.357008 -0.274597 0.121025 0.071 Uiso 1 1 calc R U . . .
C24 C 0.21627(19) 0.1595(2) 0.06021(16) 0.0581(5) Uani 1 1 d . . . . .
H24A H 0.213839 0.247099 0.005694 0.087 Uiso 1 1 calc R U . . .
H24B H 0.132347 0.143616 0.056437 0.087 Uiso 1 1 calc R U . . .
H24C H 0.293628 0.084312 0.051831 0.087 Uiso 1 1 calc R U . . .
C13 C 1.1512(2) -0.18392(19) 0.09598(15) 0.0568(5) Uani 1 1 d . . . . .
H13 H 1.148831 -0.187374 0.030581 0.068 Uiso 1 1 calc R U . . .
C6 C 1.1210(2) 0.4526(2) 0.38422(15) 0.0589(5) Uani 1 1 d . . . . .
H6 H 1.170404 0.489350 0.410187 0.071 Uiso 1 1 calc R U . . .
H2 H 1.0394(18) 0.1279(17) 0.2483(12) 0.038(4) Uiso 1 1 d . . . . .
H1 H 1.0293(17) 0.5175(18) 0.0847(14) 0.042(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2318(17) . ?
O2 C33 1.3677(19) . ?
O2 C25 1.4377(18) . ?
O3 C27 1.2165(18) . ?
O4 C21 1.3716(18) . ?
O4 C24 1.425(2) . ?
N2 C9 1.4582(18) . ?
N2 C2 1.4621(18) . ?
N2 H2 0.883(17) . ?
N1 C1 1.3467(19) . ?
N1 C8 1.4052(19) . ?
N1 H1 0.860(18) . ?
C9 C10 1.524(2) . ?
C9 C17 1.5332(19) . ?
C9 H9 0.9800 . ?
C17 C18 1.5146(19) . ?
C17 C26 1.5627(19) . ?
C17 H17 0.9800 . ?
C26 C25 1.528(2) . ?
C26 C27 1.535(2) . ?
C26 C2 1.5982(19) . ?
C3 C4 1.378(2) . ?
C3 C8 1.390(2) . ?
C3 C2 1.5140(19) . ?
C27 C28 1.480(2) . ?
C18 C19 1.378(2) . ?
C18 C23 1.395(2) . ?
C2 C1 1.5603(19) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C11 C16 1.385(2) . ?
C11 C12 1.388(2) . ?
C11 C10 1.508(2) . ?
C8 C7 1.377(2) . ?
C33 C32 1.392(2) . ?
C33 C28 1.397(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C28 C29 1.397(2) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
C21 C22 1.379(2) . ?
C21 C20 1.379(2) . ?
C23 C22 1.379(2) . ?
C23 H23 0.9300 . ?
C29 C30 1.378(3) . ?
C29 H29 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C19 C20 1.386(2) . ?
C19 H19 0.9300 . ?
C16 C15 1.380(3) . ?
C16 H16 0.9300 . ?
C22 H22 0.9300 . ?
C32 C31 1.377(3) . ?
C32 H32 0.9300 . ?
C20 H20 0.9300 . ?
C30 C31 1.382(3) . ?
C30 H30 0.9300 . ?
C7 C6 1.378(3) . ?
C7 H7 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C31 H31 0.9300 . ?
C15 C14 1.368(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.373(3) . ?
C14 H14 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?

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
C33 O2 C25 114.56(12) . . ?
C21 O4 C24 117.62(13) . . ?
C9 N2 C2 108.28(11) . . ?
C9 N2 H2 115.3(10) . . ?
C2 N2 H2 111.0(10) . . ?
C1 N1 C8 111.65(12) . . ?
C1 N1 H1 122.5(11) . . ?
C8 N1 H1 124.7(11) . . ?
N2 C9 C10 111.05(12) . . ?
N2 C9 C17 100.32(11) . . ?
C10 C9 C17 114.01(11) . . ?
N2 C9 H9 110.4 . . ?
C10 C9 H9 110.4 . . ?
C17 C9 H9 110.4 . . ?
C18 C17 C9 115.64(12) . . ?
C18 C17 C26 117.25(11) . . ?
C9 C17 C26 104.18(10) . . ?
C18 C17 H17 106.3 . . ?
C9 C17 H17 106.3 . . ?
C26 C17 H17 106.3 . . ?
C25 C26 C27 105.18(12) . . ?
C25 C26 C17 112.90(11) . . ?
C27 C26 C17 111.61(11) . . ?
C25 C26 C2 113.60(11) . . ?
C27 C26 C2 110.15(11) . . ?
C17 C26 C2 103.56(10) . . ?
C4 C3 C8 119.60(13) . . ?
C4 C3 C2 130.93(13) . . ?
C8 C3 C2 109.31(12) . . ?
O3 C27 C28 122.21(14) . . ?
O3 C27 C26 122.63(14) . . ?
C28 C27 C26 115.15(13) . . ?
C19 C18 C23 116.56(14) . . ?
C19 C18 C17 123.31(13) . . ?
C23 C18 C17 120.09(13) . . ?
N2 C2 C3 111.02(11) . . ?
N2 C2 C1 112.18(11) . . ?
C3 C2 C1 100.78(11) . . ?
N2 C2 C26 102.68(10) . . ?
C3 C2 C26 118.16(11) . . ?
C1 C2 C26 112.39(11) . . ?
O2 C25 C26 112.00(12) . . ?
O2 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
O2 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C16 C11 C12 117.74(15) . . ?
C16 C11 C10 121.25(15) . . ?
C12 C11 C10 120.97(14) . . ?
C7 C8 C3 122.04(14) . . ?
C7 C8 N1 128.36(14) . . ?
C3 C8 N1 109.57(13) . . ?
O1 C1 N1 125.78(13) . . ?
O1 C1 C2 125.58(13) . . ?
N1 C1 C2 108.57(12) . . ?
O2 C33 C32 117.33(15) . . ?
O2 C33 C28 121.88(14) . . ?
C32 C33 C28 120.79(16) . . ?
C11 C10 C9 112.45(12) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C33 C28 C29 118.45(15) . . ?
C33 C28 C27 120.45(14) . . ?
C29 C28 C27 121.00(15) . . ?
C3 C4 C5 118.91(15) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
O4 C21 C22 116.45(14) . . ?
O4 C21 C20 124.29(15) . . ?
C22 C21 C20 119.25(14) . . ?
C22 C23 C18 121.76(15) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 119.1 . . ?
C30 C29 C28 120.84(19) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C13 C12 C11 121.18(16) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C18 C19 C20 122.49(14) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C15 C16 C11 120.87(17) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C23 C22 C21 120.28(14) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C31 C32 C33 119.12(19) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C21 C20 C19 119.62(15) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C29 C30 C31 119.60(18) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C8 C7 C6 117.54(16) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C6 C5 C4 120.41(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C32 C31 C30 121.16(18) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C14 C15 C16 120.70(18) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C14 C13 119.58(17) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C14 C13 C12 119.92(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C7 C6 C5 121.44(16) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C9 C10 -168.22(11) . . . . ?
C2 N2 C9 C17 -47.34(13) . . . . ?
N2 C9 C17 C18 169.21(11) . . . . ?
C10 C9 C17 C18 -72.05(16) . . . . ?
N2 C9 C17 C26 39.04(13) . . . . ?
C10 C9 C17 C26 157.78(12) . . . . ?
C18 C17 C26 C25 -24.72(17) . . . . ?
C9 C17 C26 C25 104.48(13) . . . . ?
C18 C17 C26 C27 93.51(14) . . . . ?
C9 C17 C26 C27 -137.28(12) . . . . ?
C18 C17 C26 C2 -148.02(12) . . . . ?
C9 C17 C26 C2 -18.81(13) . . . . ?
C25 C26 C27 O3 142.46(15) . . . . ?
C17 C26 C27 O3 19.69(19) . . . . ?
C2 C26 C27 O3 -94.76(16) . . . . ?
C25 C26 C27 C28 -38.61(16) . . . . ?
C17 C26 C27 C28 -161.37(12) . . . . ?
C2 C26 C27 C28 84.17(15) . . . . ?
C9 C17 C18 C19 -37.0(2) . . . . ?
C26 C17 C18 C19 86.57(18) . . . . ?
C9 C17 C18 C23 140.68(14) . . . . ?
C26 C17 C18 C23 -95.76(16) . . . . ?
C9 N2 C2 C3 162.22(11) . . . . ?
C9 N2 C2 C1 -85.87(13) . . . . ?
C9 N2 C2 C26 35.01(13) . . . . ?
C4 C3 C2 N2 -54.0(2) . . . . ?
C8 C3 C2 N2 121.35(13) . . . . ?
C4 C3 C2 C1 -173.01(16) . . . . ?
C8 C3 C2 C1 2.34(15) . . . . ?
C4 C3 C2 C26 64.2(2) . . . . ?
C8 C3 C2 C26 -120.46(13) . . . . ?
C25 C26 C2 N2 -131.15(12) . . . . ?
C27 C26 C2 N2 111.16(12) . . . . ?
C17 C26 C2 N2 -8.31(13) . . . . ?
C25 C26 C2 C3 106.34(14) . . . . ?
C27 C26 C2 C3 -11.35(16) . . . . ?
C17 C26 C2 C3 -130.82(12) . . . . ?
C25 C26 C2 C1 -10.40(16) . . . . ?
C27 C26 C2 C1 -128.09(12) . . . . ?
C17 C26 C2 C1 112.44(12) . . . . ?
C33 O2 C25 C26 -53.90(16) . . . . ?
C27 C26 C25 O2 62.93(14) . . . . ?
C17 C26 C25 O2 -175.14(11) . . . . ?
C2 C26 C25 O2 -57.60(16) . . . . ?
C4 C3 C8 C7 -2.5(2) . . . . ?
C2 C3 C8 C7 -178.42(15) . . . . ?
C4 C3 C8 N1 175.40(14) . . . . ?
C2 C3 C8 N1 -0.56(17) . . . . ?
C1 N1 C8 C7 175.82(16) . . . . ?
C1 N1 C8 C3 -1.87(17) . . . . ?
C8 N1 C1 O1 -173.53(14) . . . . ?
C8 N1 C1 C2 3.41(16) . . . . ?
N2 C2 C1 O1 55.34(18) . . . . ?
C3 C2 C1 O1 173.51(14) . . . . ?
C26 C2 C1 O1 -59.77(18) . . . . ?
N2 C2 C1 N1 -121.61(13) . . . . ?
C3 C2 C1 N1 -3.44(14) . . . . ?
C26 C2 C1 N1 123.28(12) . . . . ?
C25 O2 C33 C32 -162.03(13) . . . . ?
C25 O2 C33 C28 17.0(2) . . . . ?
C16 C11 C10 C9 96.13(17) . . . . ?
C12 C11 C10 C9 -81.36(18) . . . . ?
N2 C9 C10 C11 -67.04(16) . . . . ?
C17 C9 C10 C11 -179.47(12) . . . . ?
O2 C33 C28 C29 -176.92(14) . . . . ?
C32 C33 C28 C29 2.1(2) . . . . ?
O2 C33 C28 C27 6.7(2) . . . . ?
C32 C33 C28 C27 -174.26(14) . . . . ?
O3 C27 C28 C33 -174.37(15) . . . . ?
C26 C27 C28 C33 6.7(2) . . . . ?
O3 C27 C28 C29 9.4(2) . . . . ?
C26 C27 C28 C29 -169.58(14) . . . . ?
C8 C3 C4 C5 2.6(2) . . . . ?
C2 C3 C4 C5 177.54(16) . . . . ?
C24 O4 C21 C22 -172.22(16) . . . . ?
C24 O4 C21 C20 7.2(2) . . . . ?
C19 C18 C23 C22 0.9(2) . . . . ?
C17 C18 C23 C22 -176.88(15) . . . . ?
C33 C28 C29 C30 -0.7(2) . . . . ?
C27 C28 C29 C30 175.63(15) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C12 C13 177.11(15) . . . . ?
C23 C18 C19 C20 -1.3(3) . . . . ?
C17 C18 C19 C20 176.49(15) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C10 C11 C16 C15 -177.41(16) . . . . ?
C18 C23 C22 C21 0.6(3) . . . . ?
O4 C21 C22 C23 177.64(15) . . . . ?
C20 C21 C22 C23 -1.8(3) . . . . ?
O2 C33 C32 C31 177.15(15) . . . . ?
C28 C33 C32 C31 -1.9(2) . . . . ?
O4 C21 C20 C19 -177.90(16) . . . . ?
C22 C21 C20 C19 1.5(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C28 C29 C30 C31 -0.9(3) . . . . ?
C3 C8 C7 C6 0.7(3) . . . . ?
N1 C8 C7 C6 -176.74(17) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C33 C32 C31 C30 0.3(3) . . . . ?
C29 C30 C31 C32 1.1(3) . . . . ?
C11 C16 C15 C14 0.4(3) . . . . ?
C16 C15 C14 C13 -0.8(3) . . . . ?
C15 C14 C13 C12 0.5(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C8 C7 C6 C5 0.9(3) . . . . ?
C4 C5 C6 C7 -0.7(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
C9 H9 O1 0.98 2.61 3.2134(18) 119.7 . yes
C17 H17 O3 0.98 2.33 2.8303(18) 110.7 . yes
C25 H25A O1 0.97 2.42 2.9855(19) 116.9 . yes
N2 H2 O4 0.883(17) 2.295(17) 3.1254(17) 156.7(14) 1_655 yes
N1 H1 O1 0.860(18) 2.047(18) 2.9018(17) 172.5(15) 2_765 yes

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041



