# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2314963'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2023-12-17 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N2 O2'
_chemical_formula_sum            'C23 H22 N2 O2'
_chemical_formula_weight         358.42

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.9870(9)
_cell_length_b                   17.1569(16)
_cell_length_c                   24.1034(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3716.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      1.69
_cell_measurement_theta_max      27.97

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            15712
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.690
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3294
_reflns_number_gt                1591
_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       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3294
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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 0.5024(2) 0.62279(11) 0.55534(9) 0.0641(5) Uani 1 1 d . . . . .
O2 O 0.3982(2) 0.58527(12) 0.63406(9) 0.0763(6) Uani 1 1 d . . . . .
N1 N 0.5537(2) 0.40679(14) 0.67905(10) 0.0574(6) Uani 1 1 d . . . . .
N2 N 0.7114(2) 0.39183(13) 0.60852(10) 0.0545(6) Uani 1 1 d . . . . .
C1 C 0.4987(4) 0.5772(2) 0.84480(15) 0.0930(11) Uani 1 1 d . . . . .
H1A H 0.584989 0.552636 0.860479 0.140 Uiso 1 1 calc R U . . .
H1B H 0.429865 0.589956 0.873866 0.140 Uiso 1 1 calc R U . . .
H1C H 0.527842 0.623885 0.825779 0.140 Uiso 1 1 calc R U . . .
C2 C 0.4262(4) 0.5228(2) 0.80482(16) 0.0957(12) Uani 1 1 d . . . . .
H2A H 0.385526 0.479075 0.825368 0.115 Uiso 1 1 calc R U . . .
H2B H 0.343640 0.549631 0.787299 0.115 Uiso 1 1 calc R U . . .
C3 C 0.5229(3) 0.4930(2) 0.76211(14) 0.0821(10) Uani 1 1 d . . . . .
H3A H 0.601525 0.463089 0.779571 0.099 Uiso 1 1 calc R U . . .
H3B H 0.569046 0.536815 0.743344 0.099 Uiso 1 1 calc R U . . .
C4 C 0.4453(3) 0.44050(18) 0.71760(13) 0.0674(9) Uani 1 1 d . . . . .
H4A H 0.391624 0.398873 0.736066 0.081 Uiso 1 1 calc R U . . .
H4B H 0.373859 0.471423 0.696978 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6373(3) 0.33889(17) 0.68838(13) 0.0556(7) Uani 1 1 d . . . . .
C6 C 0.6347(3) 0.28634(19) 0.73215(13) 0.0672(9) Uani 1 1 d . . . . .
H6 H 0.570037 0.292885 0.761912 0.081 Uiso 1 1 calc R U . . .
C7 C 0.7315(4) 0.22404(19) 0.72986(15) 0.0750(9) Uani 1 1 d . . . . .
H7 H 0.732204 0.188116 0.758753 0.090 Uiso 1 1 calc R U . . .
C8 C 0.8282(4) 0.21365(19) 0.68533(16) 0.0746(9) Uani 1 1 d . . . . .
H8 H 0.891222 0.170668 0.685006 0.090 Uiso 1 1 calc R U . . .
C9 C 0.8327(3) 0.26572(18) 0.64158(14) 0.0659(8) Uani 1 1 d . . . . .
H9 H 0.897447 0.258841 0.611874 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7359(3) 0.32888(17) 0.64407(12) 0.0551(7) Uani 1 1 d . . . . .
C11 C 0.7661(3) 0.42367(17) 0.55941(12) 0.0589(8) Uani 1 1 d . . . . .
H11 H 0.840136 0.402832 0.536884 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6895(3) 0.49180(17) 0.55078(12) 0.0533(7) Uani 1 1 d . . . . .
C13 C 0.6982(3) 0.55028(17) 0.50733(12) 0.0539(7) Uani 1 1 d . . . . .
C14 C 0.7942(3) 0.54753(19) 0.46212(13) 0.0664(8) Uani 1 1 d . . . . .
H14 H 0.858668 0.505528 0.458059 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7946(3) 0.6067(2) 0.42316(13) 0.0724(9) Uani 1 1 d . . . . .
H15 H 0.860509 0.604032 0.393457 0.087 Uiso 1 1 calc R U . . .
C16 C 0.6982(3) 0.67036(19) 0.42743(13) 0.0659(9) Uani 1 1 d . . . . .
C17 C 0.7044(4) 0.7336(2) 0.38379(15) 0.0870(11) Uani 1 1 d . . . . .
H17A H 0.734781 0.781733 0.400646 0.131 Uiso 1 1 calc R U . . .
H17B H 0.607808 0.739931 0.367427 0.131 Uiso 1 1 calc R U . . .
H17C H 0.774726 0.719260 0.355580 0.131 Uiso 1 1 calc R U . . .
C18 C 0.5997(3) 0.67496(17) 0.47234(13) 0.0609(8) Uani 1 1 d . . . . .
C19 C 0.4937(4) 0.74265(19) 0.47877(14) 0.0815(10) Uani 1 1 d . . . . .
H19A H 0.426089 0.743621 0.447945 0.122 Uiso 1 1 calc R U . . .
H19B H 0.549084 0.790483 0.479796 0.122 Uiso 1 1 calc R U . . .
H19C H 0.438626 0.736888 0.512639 0.122 Uiso 1 1 calc R U . . .
C20 C 0.6031(3) 0.61446(17) 0.51129(12) 0.0555(7) Uani 1 1 d . . . . .
C21 C 0.4887(3) 0.56926(17) 0.59825(13) 0.0573(8) Uani 1 1 d . . . . .
C22 C 0.5847(3) 0.50308(17) 0.59486(11) 0.0513(7) Uani 1 1 d . . . . .
C23 C 0.6022(3) 0.43880(17) 0.63022(12) 0.0516(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.389(3) . ?
O1 C20 1.402(3) . ?
O2 C21 1.217(3) . ?
N1 C23 1.370(3) . ?
N1 C5 1.405(3) . ?
N1 C4 1.465(3) . ?
N2 C23 1.373(3) . ?
N2 C11 1.394(3) . ?
N2 C10 1.396(3) . ?
C1 C2 1.491(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.441(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.565(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.388(4) . ?
C5 C10 1.398(4) . ?
C6 C7 1.379(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9300 . ?
C12 C22 1.432(4) . ?
C12 C13 1.452(4) . ?
C13 C14 1.391(4) . ?
C13 C20 1.397(4) . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.399(4) . ?
C15 H15 0.9300 . ?
C16 C18 1.401(4) . ?
C16 C17 1.512(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C20 1.400(4) . ?
C18 C19 1.510(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.429(4) . ?
C22 C23 1.403(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O1 C20 123.6(2) . . ?
C23 N1 C5 107.4(2) . . ?
C23 N1 C4 126.7(2) . . ?
C5 N1 C4 125.6(3) . . ?
C23 N2 C11 110.2(2) . . ?
C23 N2 C10 109.5(2) . . ?
C11 N2 C10 140.2(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 114.8(3) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 115.2(3) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N1 C4 C3 111.5(2) . . ?
N1 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C10 120.8(3) . . ?
C6 C5 N1 130.6(3) . . ?
C10 C5 N1 108.6(3) . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C8 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 116.9(3) . . ?
C8 C9 H9 121.6 . . ?
C10 C9 H9 121.6 . . ?
C9 C10 N2 132.4(3) . . ?
C9 C10 C5 121.7(3) . . ?
N2 C10 C5 105.9(2) . . ?
C12 C11 N2 106.6(2) . . ?
C12 C11 H11 126.7 . . ?
N2 C11 H11 126.7 . . ?
C11 C12 C22 109.4(3) . . ?
C11 C12 C13 132.1(3) . . ?
C22 C12 C13 118.5(2) . . ?
C14 C13 C20 117.4(3) . . ?
C14 C13 C12 125.1(3) . . ?
C20 C13 C12 117.5(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C18 119.5(3) . . ?
C15 C16 C17 119.1(3) . . ?
C18 C16 C17 121.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C16 117.6(3) . . ?
C20 C18 C19 121.0(3) . . ?
C16 C18 C19 121.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 C18 123.5(3) . . ?
C13 C20 O1 121.8(3) . . ?
C18 C20 O1 114.7(3) . . ?
O2 C21 O1 116.0(3) . . ?
O2 C21 C22 128.6(3) . . ?
O1 C21 C22 115.4(3) . . ?
C23 C22 C21 131.1(3) . . ?
C23 C22 C12 105.7(2) . . ?
C21 C22 C12 123.2(3) . . ?
N1 C23 N2 108.6(2) . . ?
N1 C23 C22 143.3(3) . . ?
N2 C23 C22 108.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -176.0(3) . . . . ?
C23 N1 C4 C3 -89.8(3) . . . . ?
C5 N1 C4 C3 83.7(3) . . . . ?
C2 C3 C4 N1 -174.5(3) . . . . ?
C23 N1 C5 C6 178.4(3) . . . . ?
C4 N1 C5 C6 3.8(5) . . . . ?
C23 N1 C5 C10 -1.1(3) . . . . ?
C4 N1 C5 C10 -175.6(2) . . . . ?
C10 C5 C6 C7 -0.6(4) . . . . ?
N1 C5 C6 C7 -180.0(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 N2 179.3(3) . . . . ?
C8 C9 C10 C5 -0.7(4) . . . . ?
C23 N2 C10 C9 -179.9(3) . . . . ?
C11 N2 C10 C9 -3.3(5) . . . . ?
C23 N2 C10 C5 0.1(3) . . . . ?
C11 N2 C10 C5 176.7(3) . . . . ?
C6 C5 C10 C9 1.1(4) . . . . ?
N1 C5 C10 C9 -179.4(2) . . . . ?
C6 C5 C10 N2 -178.9(2) . . . . ?
N1 C5 C10 N2 0.6(3) . . . . ?
C23 N2 C11 C12 0.2(3) . . . . ?
C10 N2 C11 C12 -176.4(3) . . . . ?
N2 C11 C12 C22 -0.2(3) . . . . ?
N2 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C22 C12 C13 C14 179.8(3) . . . . ?
C11 C12 C13 C20 -179.4(3) . . . . ?
C22 C12 C13 C20 0.0(4) . . . . ?
C20 C13 C14 C15 0.3(4) . . . . ?
C12 C13 C14 C15 -179.5(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C18 0.6(4) . . . . ?
C14 C15 C16 C17 179.6(3) . . . . ?
C15 C16 C18 C20 0.0(4) . . . . ?
C17 C16 C18 C20 -178.9(3) . . . . ?
C15 C16 C18 C19 179.9(3) . . . . ?
C17 C16 C18 C19 0.9(4) . . . . ?
C14 C13 C20 C18 0.3(4) . . . . ?
C12 C13 C20 C18 -179.9(3) . . . . ?
C14 C13 C20 O1 -179.9(2) . . . . ?
C12 C13 C20 O1 -0.1(4) . . . . ?
C16 C18 C20 C13 -0.5(4) . . . . ?
C19 C18 C20 C13 179.7(3) . . . . ?
C16 C18 C20 O1 179.7(2) . . . . ?
C19 C18 C20 O1 -0.2(4) . . . . ?
C21 O1 C20 C13 0.3(4) . . . . ?
C21 O1 C20 C18 -179.9(2) . . . . ?
C20 O1 C21 O2 178.7(2) . . . . ?
C20 O1 C21 C22 -0.4(3) . . . . ?
O2 C21 C22 C23 0.5(5) . . . . ?
O1 C21 C22 C23 179.5(3) . . . . ?
O2 C21 C22 C12 -178.6(3) . . . . ?
O1 C21 C22 C12 0.4(4) . . . . ?
C11 C12 C22 C23 0.1(3) . . . . ?
C13 C12 C22 C23 -179.5(2) . . . . ?
C11 C12 C22 C21 179.3(2) . . . . ?
C13 C12 C22 C21 -0.2(4) . . . . ?
C5 N1 C23 N2 1.2(3) . . . . ?
C4 N1 C23 N2 175.6(2) . . . . ?
C5 N1 C23 C22 -176.2(3) . . . . ?
C4 N1 C23 C22 -1.7(5) . . . . ?
C11 N2 C23 N1 -178.5(2) . . . . ?
C10 N2 C23 N1 -0.9(3) . . . . ?
C11 N2 C23 C22 -0.2(3) . . . . ?
C10 N2 C23 C22 177.5(2) . . . . ?
C21 C22 C23 N1 -1.8(6) . . . . ?
C12 C22 C23 N1 177.5(3) . . . . ?
C21 C22 C23 N2 -179.1(3) . . . . ?
C12 C22 C23 N2 0.1(3) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 2314966'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2023-12-17 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O2'
_chemical_formula_sum            'C26 H22 N2 O2'
_chemical_formula_weight         394.45

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/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                   19.6400(16)
_cell_length_b                   14.6692(16)
_cell_length_c                   7.1693(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.833(7)
_cell_angle_gamma                90
_cell_volume                     2050.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10262
_cell_measurement_theta_min      1.39
_cell_measurement_theta_max      26.93

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.790
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9354
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            4280
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.737
_diffrn_reflns_theta_max         26.719
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4280
_reflns_number_gt                1909
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4280
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_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 0.75615(9) 0.13090(11) 0.9505(2) 0.0664(5) Uani 1 1 d . . . . .
O2 O 0.86633(10) 0.12205(13) 1.0519(3) 0.0827(6) Uani 1 1 d . . . . .
N1 N 0.83352(12) 0.56372(17) 0.7535(3) 0.0701(6) Uani 1 1 d . . . . .
H1N H 0.8304(14) 0.507(2) 0.703(4) 0.090(10) Uiso 1 1 d . . . . .
N2 N 0.84685(9) 0.41517(14) 1.0110(3) 0.0548(5) Uani 1 1 d . . . . .
C1 C 0.70112(17) 0.6354(2) 0.5431(4) 0.0892(9) Uani 1 1 d . . . . .
H1 H 0.698687 0.636185 0.671834 0.107 Uiso 1 1 calc R U . . .
C2 C 0.6418(2) 0.6386(3) 0.4193(6) 0.1096(11) Uani 1 1 d . . . . .
H2 H 0.599511 0.642210 0.465059 0.132 Uiso 1 1 calc R U . . .
C3 C 0.6447(3) 0.6366(2) 0.2327(7) 0.1166(13) Uani 1 1 d . . . . .
H3 H 0.604402 0.639168 0.150424 0.140 Uiso 1 1 calc R U . . .
C4 C 0.7068(3) 0.6309(3) 0.1625(5) 0.1224(14) Uani 1 1 d . . . . .
H4 H 0.708887 0.628686 0.033676 0.147 Uiso 1 1 calc R U . . .
C5 C 0.7665(2) 0.6284(2) 0.2882(5) 0.0953(10) Uani 1 1 d . . . . .
H5 H 0.808743 0.624959 0.242078 0.114 Uiso 1 1 calc R U . . .
C6 C 0.76442(16) 0.63098(18) 0.4760(4) 0.0717(7) Uani 1 1 d . . . . .
C7 C 0.83018(16) 0.6351(2) 0.6123(5) 0.0893(9) Uani 1 1 d . . . . .
H7A H 0.869297 0.629525 0.542242 0.107 Uiso 1 1 calc R U . . .
H7B H 0.833028 0.693984 0.674301 0.107 Uiso 1 1 calc R U . . .
C8 C 0.87993(12) 0.56913(18) 0.9154(4) 0.0615(7) Uani 1 1 d . . . . .
C9 C 0.91991(14) 0.64698(19) 0.9629(4) 0.0756(8) Uani 1 1 d . . . . .
H9 H 0.916419 0.696942 0.882455 0.091 Uiso 1 1 calc R U . . .
C10 C 0.96496(15) 0.6504(3) 1.1295(6) 0.0900(10) Uani 1 1 d . . . . .
H10 H 0.990396 0.703063 1.158890 0.108 Uiso 1 1 calc R U . . .
C11 C 0.97220(14) 0.5780(3) 1.2495(5) 0.0936(10) Uani 1 1 d . . . . .
H11 H 1.003390 0.580275 1.357723 0.112 Uiso 1 1 calc R U . . .
C12 C 0.93255(12) 0.5011(2) 1.2082(4) 0.0797(9) Uani 1 1 d . . . . .
H12 H 0.936412 0.451887 1.290505 0.096 Uiso 1 1 calc R U . . .
C13 C 0.88690(11) 0.49676(18) 1.0443(4) 0.0592(6) Uani 1 1 d . . . . .
C14 C 0.77647(11) 0.41171(17) 0.9555(3) 0.0531(6) Uani 1 1 d . . . . .
H14 H 0.747611 0.461612 0.930590 0.064 Uiso 1 1 calc R U . . .
C15 C 0.75729(11) 0.32232(16) 0.9439(3) 0.0480(6) Uani 1 1 d . . . . .
C16 C 0.69268(11) 0.27383(16) 0.8883(3) 0.0497(6) Uani 1 1 d . . . . .
C17 C 0.62854(11) 0.31491(17) 0.8274(3) 0.0550(6) Uani 1 1 d . . . . .
C18 C 0.62130(12) 0.41692(18) 0.8155(4) 0.0720(8) Uani 1 1 d . . . . .
H18A H 0.574365 0.432406 0.775150 0.108 Uiso 1 1 calc R U . . .
H18B H 0.649943 0.440274 0.727016 0.108 Uiso 1 1 calc R U . . .
H18C H 0.634965 0.443171 0.936888 0.108 Uiso 1 1 calc R U . . .
C19 C 0.57224(12) 0.2583(2) 0.7765(4) 0.0693(7) Uani 1 1 d . . . . .
H19 H 0.530077 0.285227 0.737329 0.083 Uiso 1 1 calc R U . . .
C20 C 0.57614(14) 0.1650(2) 0.7815(4) 0.0695(8) Uani 1 1 d . . . . .
C21 C 0.51334(15) 0.1061(2) 0.7250(5) 0.1074(12) Uani 1 1 d . . . . .
H21A H 0.472737 0.142829 0.721382 0.161 Uiso 1 1 calc R U . . .
H21B H 0.511497 0.057944 0.814847 0.161 Uiso 1 1 calc R U . . .
H21C H 0.516130 0.080416 0.602952 0.161 Uiso 1 1 calc R U . . .
C22 C 0.63900(14) 0.12477(19) 0.8401(3) 0.0677(7) Uani 1 1 d . . . . .
H22 H 0.643211 0.061630 0.843838 0.081 Uiso 1 1 calc R U . . .
C23 C 0.69537(12) 0.17962(16) 0.8928(3) 0.0550(6) Uani 1 1 d . . . . .
C24 C 0.81814(14) 0.17263(18) 1.0038(4) 0.0622(7) Uani 1 1 d . . . . .
C25 C 0.81764(11) 0.26982(16) 0.9974(3) 0.0523(6) Uani 1 1 d . . . . .
C26 C 0.87142(12) 0.32972(17) 1.0372(3) 0.0601(7) Uani 1 1 d . . . . .
H26 H 0.916790 0.313952 1.075595 0.072 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C24 1.376(3) . ?
O1 C23 1.411(3) . ?
O2 C24 1.220(3) . ?
N1 C8 1.390(3) . ?
N1 C7 1.453(3) . ?
N1 H1N 0.90(3) . ?
N2 C26 1.348(3) . ?
N2 C14 1.393(3) . ?
N2 C13 1.436(3) . ?
C1 C2 1.379(5) . ?
C1 C6 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.352(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.525(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.403(3) . ?
C8 C9 1.405(3) . ?
C9 C10 1.400(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.364(3) . ?
C14 H14 0.9300 . ?
C15 C25 1.427(3) . ?
C15 C16 1.468(3) . ?
C16 C23 1.383(3) . ?
C16 C17 1.418(3) . ?
C17 C19 1.396(3) . ?
C17 C18 1.505(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9300 . ?
C20 C22 1.387(4) . ?
C20 C21 1.521(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9300 . ?
C24 C25 1.426(3) . ?
C25 C26 1.377(3) . ?
C26 H26 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
C24 O1 C23 123.10(19) . . ?
C8 N1 C7 120.8(2) . . ?
C8 N1 H1N 113.3(18) . . ?
C7 N1 H1N 112.6(18) . . ?
C26 N2 C14 109.4(2) . . ?
C26 N2 C13 124.87(19) . . ?
C14 N2 C13 125.7(2) . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 121.0(3) . . ?
C1 C6 C7 120.1(3) . . ?
N1 C7 C6 112.5(2) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C13 120.6(2) . . ?
N1 C8 C9 122.7(3) . . ?
C13 C8 C9 116.6(2) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 121.6(2) . . ?
C12 C13 N2 117.6(3) . . ?
C8 C13 N2 120.8(2) . . ?
C15 C14 N2 108.0(2) . . ?
C15 C14 H14 126.0 . . ?
N2 C14 H14 126.0 . . ?
C14 C15 C25 106.74(19) . . ?
C14 C15 C16 134.9(2) . . ?
C25 C15 C16 118.3(2) . . ?
C23 C16 C17 117.5(2) . . ?
C23 C16 C15 116.6(2) . . ?
C17 C16 C15 125.8(2) . . ?
C19 C17 C16 118.4(2) . . ?
C19 C17 C18 120.7(2) . . ?
C16 C17 C18 121.0(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 123.1(2) . . ?
C20 C19 H19 118.4 . . ?
C17 C19 H19 118.4 . . ?
C19 C20 C22 118.5(2) . . ?
C19 C20 C21 121.3(3) . . ?
C22 C20 C21 120.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 119.3(3) . . ?
C23 C22 H22 120.4 . . ?
C20 C22 H22 120.4 . . ?
C16 C23 C22 123.2(2) . . ?
C16 C23 O1 122.8(2) . . ?
C22 C23 O1 114.0(2) . . ?
O2 C24 O1 116.0(2) . . ?
O2 C24 C25 128.3(3) . . ?
O1 C24 C25 115.7(2) . . ?
C26 C25 C24 129.0(2) . . ?
C26 C25 C15 107.7(2) . . ?
C24 C25 C15 123.4(2) . . ?
N2 C26 C25 108.1(2) . . ?
N2 C26 H26 125.9 . . ?
C25 C26 H26 125.9 . . ?

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
C6 C1 C2 C3 0.6(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C4 C5 C6 C7 -175.6(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C2 C1 C6 C7 175.1(3) . . . . ?
C8 N1 C7 C6 -163.9(2) . . . . ?
C5 C6 C7 N1 -126.6(3) . . . . ?
C1 C6 C7 N1 57.3(4) . . . . ?
C7 N1 C8 C13 -174.8(2) . . . . ?
C7 N1 C8 C9 7.7(4) . . . . ?
N1 C8 C9 C10 178.5(3) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -2.2(5) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C11 C12 C13 N2 -179.4(2) . . . . ?
N1 C8 C13 C12 -179.4(2) . . . . ?
C9 C8 C13 C12 -1.7(3) . . . . ?
N1 C8 C13 N2 0.7(4) . . . . ?
C9 C8 C13 N2 178.3(2) . . . . ?
C26 N2 C13 C12 -43.9(3) . . . . ?
C14 N2 C13 C12 132.9(2) . . . . ?
C26 N2 C13 C8 136.1(2) . . . . ?
C14 N2 C13 C8 -47.1(3) . . . . ?
C26 N2 C14 C15 -1.1(3) . . . . ?
C13 N2 C14 C15 -178.3(2) . . . . ?
N2 C14 C15 C25 1.1(3) . . . . ?
N2 C14 C15 C16 -177.5(2) . . . . ?
C14 C15 C16 C23 178.6(3) . . . . ?
C25 C15 C16 C23 0.2(3) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C25 C15 C16 C17 -178.5(2) . . . . ?
C23 C16 C17 C19 0.2(3) . . . . ?
C15 C16 C17 C19 178.9(2) . . . . ?
C23 C16 C17 C18 -179.1(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C19 C20 -0.4(4) . . . . ?
C18 C17 C19 C20 178.9(3) . . . . ?
C17 C19 C20 C22 0.1(4) . . . . ?
C17 C19 C20 C21 179.9(3) . . . . ?
C19 C20 C22 C23 0.5(4) . . . . ?
C21 C20 C22 C23 -179.3(3) . . . . ?
C17 C16 C23 C22 0.4(4) . . . . ?
C15 C16 C23 C22 -178.4(2) . . . . ?
C17 C16 C23 O1 179.9(2) . . . . ?
C15 C16 C23 O1 1.1(3) . . . . ?
C20 C22 C23 C16 -0.8(4) . . . . ?
C20 C22 C23 O1 179.7(2) . . . . ?
C24 O1 C23 C16 -1.3(3) . . . . ?
C24 O1 C23 C22 178.3(2) . . . . ?
C23 O1 C24 O2 179.4(2) . . . . ?
C23 O1 C24 C25 0.0(3) . . . . ?
O2 C24 C25 C26 2.5(5) . . . . ?
O1 C24 C25 C26 -178.2(2) . . . . ?
O2 C24 C25 C15 -178.0(3) . . . . ?
O1 C24 C25 C15 1.4(4) . . . . ?
C14 C15 C25 C26 -0.7(3) . . . . ?
C16 C15 C25 C26 178.1(2) . . . . ?
C14 C15 C25 C24 179.7(2) . . . . ?
C16 C15 C25 C24 -1.5(4) . . . . ?
C14 N2 C26 C25 0.6(3) . . . . ?
C13 N2 C26 C25 177.9(2) . . . . ?
C24 C25 C26 N2 179.7(2) . . . . ?
C15 C25 C26 N2 0.1(3) . . . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_2j
_database_code_depnum_ccdc_archive 'CCDC 2314965'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2023-12-17 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40

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                   8.0850(16)
_cell_length_b                   9.5451(18)
_cell_length_c                   12.413(3)
_cell_angle_alpha                103.148(16)
_cell_angle_beta                 100.212(16)
_cell_angle_gamma                100.313(16)
_cell_volume                     893.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6596
_cell_measurement_theta_min      1.73
_cell_measurement_theta_max      27.37

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            9482
_diffrn_reflns_av_unetI/netI     0.1114
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.730
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3167
_reflns_number_gt                1346
_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       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0172P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1585
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_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 0.4374(3) 1.0950(2) 0.73487(18) 0.0799(7) Uani 1 1 d . . . . .
O2 O 0.0641(3) 0.6104(2) 0.27871(18) 0.0629(6) Uani 1 1 d . . . . .
O3 O 0.0413(3) 0.8087(2) 0.40190(18) 0.0718(7) Uani 1 1 d . . . . .
N1 N 0.2071(3) 0.8030(3) 0.6784(2) 0.0551(7) Uani 1 1 d . . . . .
N2 N 0.2711(3) 0.5841(3) 0.6371(2) 0.0545(7) Uani 1 1 d . . . . .
C1 C 0.5760(5) 1.1891(4) 0.7141(3) 0.0912(12) Uani 1 1 d . . . . .
H1A H 0.609411 1.138810 0.647991 0.137 Uiso 1 1 calc R U . . .
H1B H 0.672025 1.216620 0.778440 0.137 Uiso 1 1 calc R U . . .
H1C H 0.541316 1.276261 0.701515 0.137 Uiso 1 1 calc R U . . .
C2 C 0.2955(4) 1.0446(3) 0.6421(3) 0.0666(9) Uani 1 1 d . . . . .
H2A H 0.330917 0.995676 0.575415 0.080 Uiso 1 1 calc R U . . .
H2B H 0.251951 1.127861 0.626318 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1561(4) 0.9390(3) 0.6668(3) 0.0605(9) Uani 1 1 d . . . . .
H3A H 0.127037 0.986460 0.736525 0.073 Uiso 1 1 calc R U . . .
H3B H 0.053640 0.914776 0.605873 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2749(4) 0.7736(4) 0.7799(3) 0.0585(9) Uani 1 1 d . . . . .
C5 C 0.3058(4) 0.8558(4) 0.8912(3) 0.0733(11) Uani 1 1 d . . . . .
H5 H 0.282791 0.949317 0.908911 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3715(5) 0.7956(4) 0.9750(3) 0.0831(11) Uani 1 1 d . . . . .
H6 H 0.395249 0.849973 1.050514 0.100 Uiso 1 1 calc R U . . .
C7 C 0.4033(5) 0.6552(5) 0.9493(3) 0.0882(12) Uani 1 1 d . . . . .
H7 H 0.444193 0.616374 1.008329 0.106 Uiso 1 1 calc R U . . .
C8 C 0.3761(4) 0.5720(4) 0.8391(3) 0.0750(11) Uani 1 1 d . . . . .
H8 H 0.398573 0.478205 0.821764 0.090 Uiso 1 1 calc R U . . .
C9 C 0.3133(4) 0.6356(3) 0.7555(3) 0.0567(9) Uani 1 1 d . . . . .
C10 C 0.2805(4) 0.4663(3) 0.5510(3) 0.0554(9) Uani 1 1 d . . . . .
H10 H 0.321124 0.383658 0.560363 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2189(4) 0.4942(3) 0.4493(3) 0.0505(8) Uani 1 1 d . . . . .
C12 C 0.1957(4) 0.4162(3) 0.3313(3) 0.0493(8) Uani 1 1 d . . . . .
C13 C 0.2439(4) 0.2825(3) 0.2894(3) 0.0595(9) Uani 1 1 d . . . . .
C14 C 0.3314(4) 0.2059(3) 0.3691(3) 0.0725(10) Uani 1 1 d . . . . .
H14A H 0.252891 0.171992 0.412371 0.109 Uiso 1 1 calc R U . . .
H14B H 0.431895 0.273934 0.419786 0.109 Uiso 1 1 calc R U . . .
H14C H 0.364944 0.123066 0.325959 0.109 Uiso 1 1 calc R U . . .
C15 C 0.2118(4) 0.2215(4) 0.1730(3) 0.0694(10) Uani 1 1 d . . . . .
H15 H 0.244742 0.133775 0.146679 0.083 Uiso 1 1 calc R U . . .
C16 C 0.1331(4) 0.2850(4) 0.0941(3) 0.0692(10) Uani 1 1 d . . . . .
C17 C 0.0990(5) 0.2159(4) -0.0322(3) 0.1002(13) Uani 1 1 d . . . . .
H17A H 0.043929 0.276212 -0.072359 0.150 Uiso 1 1 calc R U . . .
H17B H 0.025048 0.118991 -0.051090 0.150 Uiso 1 1 calc R U . . .
H17C H 0.206281 0.208590 -0.053481 0.150 Uiso 1 1 calc R U . . .
C18 C 0.0873(4) 0.4152(4) 0.1353(3) 0.0667(9) Uani 1 1 d . . . . .
H18 H 0.034802 0.461300 0.084833 0.080 Uiso 1 1 calc R U . . .
C19 C 0.1183(4) 0.4785(3) 0.2507(3) 0.0586(9) Uani 1 1 d . . . . .
C20 C 0.0901(4) 0.6939(4) 0.3899(3) 0.0571(9) Uani 1 1 d . . . . .
C21 C 0.1694(4) 0.6342(3) 0.4741(3) 0.0491(8) Uani 1 1 d . . . . .
C22 C 0.2071(4) 0.6861(3) 0.5919(3) 0.0515(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.399(3) . ?
O1 C1 1.406(4) . ?
O2 C20 1.386(3) . ?
O2 C19 1.397(3) . ?
O3 C20 1.217(3) . ?
N1 C22 1.361(3) . ?
N1 C4 1.392(3) . ?
N1 C3 1.460(3) . ?
N2 C22 1.363(3) . ?
N2 C10 1.387(3) . ?
N2 C9 1.397(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.496(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.379(4) . ?
C4 C9 1.386(4) . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C21 1.446(4) . ?
C11 C12 1.446(4) . ?
C12 C19 1.389(4) . ?
C12 C13 1.414(4) . ?
C13 C15 1.387(4) . ?
C13 C14 1.510(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.385(4) . ?
C15 H15 0.9300 . ?
C16 C18 1.373(4) . ?
C16 C17 1.511(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C20 C21 1.412(4) . ?
C21 C22 1.391(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 112.6(3) . . ?
C20 O2 C19 122.6(3) . . ?
C22 N1 C4 107.7(2) . . ?
C22 N1 C3 126.2(2) . . ?
C4 N1 C3 126.0(3) . . ?
C22 N2 C10 110.1(2) . . ?
C22 N2 C9 109.3(3) . . ?
C10 N2 C9 140.5(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 110.2(3) . . ?
O1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C2 112.3(2) . . ?
N1 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C9 119.9(3) . . ?
C5 C4 N1 131.3(3) . . ?
C9 C4 N1 108.8(3) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.8(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 116.2(3) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 H8 121.9 . . ?
C8 C9 C4 122.7(3) . . ?
C8 C9 N2 131.7(3) . . ?
C4 C9 N2 105.6(3) . . ?
C11 C10 N2 107.5(2) . . ?
C11 C10 H10 126.3 . . ?
N2 C10 H10 126.3 . . ?
C10 C11 C21 107.8(3) . . ?
C10 C11 C12 134.4(3) . . ?
C21 C11 C12 117.9(3) . . ?
C19 C12 C13 116.5(3) . . ?
C19 C12 C11 116.9(3) . . ?
C13 C12 C11 126.6(3) . . ?
C15 C13 C12 119.4(3) . . ?
C15 C13 C14 119.5(3) . . ?
C12 C13 C14 121.1(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 123.2(3) . . ?
C16 C15 H15 118.4 . . ?
C13 C15 H15 118.4 . . ?
C18 C16 C15 117.2(3) . . ?
C18 C16 C17 120.7(3) . . ?
C15 C16 C17 122.1(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 120.8(3) . . ?
C16 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C12 123.0(3) . . ?
C18 C19 O2 113.8(3) . . ?
C12 C19 O2 123.3(3) . . ?
O3 C20 O2 115.7(3) . . ?
O3 C20 C21 128.6(3) . . ?
O2 C20 C21 115.7(3) . . ?
C22 C21 C20 130.1(3) . . ?
C22 C21 C11 106.2(3) . . ?
C20 C21 C11 123.6(3) . . ?
N1 C22 N2 108.6(2) . . ?
N1 C22 C21 143.0(3) . . ?
N2 C22 C21 108.4(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
C1 O1 C2 C3 177.1(3) . . . . ?
C22 N1 C3 C2 -79.8(4) . . . . ?
C4 N1 C3 C2 95.9(3) . . . . ?
O1 C2 C3 N1 -65.9(3) . . . . ?
C22 N1 C4 C5 178.8(4) . . . . ?
C3 N1 C4 C5 2.5(5) . . . . ?
C22 N1 C4 C9 -1.3(3) . . . . ?
C3 N1 C4 C9 -177.7(3) . . . . ?
C9 C4 C5 C6 -1.2(5) . . . . ?
N1 C4 C5 C6 178.7(3) . . . . ?
C4 C5 C6 C7 -1.2(5) . . . . ?
C5 C6 C7 C8 2.2(6) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C4 -1.7(5) . . . . ?
C7 C8 C9 N2 -179.9(4) . . . . ?
C5 C4 C9 C8 2.7(5) . . . . ?
N1 C4 C9 C8 -177.2(3) . . . . ?
C5 C4 C9 N2 -178.7(3) . . . . ?
N1 C4 C9 N2 1.4(3) . . . . ?
C22 N2 C9 C8 177.4(3) . . . . ?
C10 N2 C9 C8 -6.5(7) . . . . ?
C22 N2 C9 C4 -1.0(3) . . . . ?
C10 N2 C9 C4 175.1(4) . . . . ?
C22 N2 C10 C11 -0.8(3) . . . . ?
C9 N2 C10 C11 -176.8(4) . . . . ?
N2 C10 C11 C21 -0.2(3) . . . . ?
N2 C10 C11 C12 179.9(3) . . . . ?
C10 C11 C12 C19 176.4(3) . . . . ?
C21 C11 C12 C19 -3.5(4) . . . . ?
C10 C11 C12 C13 -3.6(5) . . . . ?
C21 C11 C12 C13 176.5(3) . . . . ?
C19 C12 C13 C15 -0.2(4) . . . . ?
C11 C12 C13 C15 179.8(3) . . . . ?
C19 C12 C13 C14 179.1(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C15 C16 -0.3(5) . . . . ?
C14 C13 C15 C16 -179.7(3) . . . . ?
C13 C15 C16 C18 0.6(5) . . . . ?
C13 C15 C16 C17 -179.7(3) . . . . ?
C15 C16 C18 C19 -0.4(5) . . . . ?
C17 C16 C18 C19 179.9(3) . . . . ?
C16 C18 C19 C12 -0.1(5) . . . . ?
C16 C18 C19 O2 180.0(3) . . . . ?
C13 C12 C19 C18 0.5(5) . . . . ?
C11 C12 C19 C18 -179.6(3) . . . . ?
C13 C12 C19 O2 -179.7(3) . . . . ?
C11 C12 C19 O2 0.3(4) . . . . ?
C20 O2 C19 C18 -177.3(3) . . . . ?
C20 O2 C19 C12 2.8(4) . . . . ?
C19 O2 C20 O3 177.8(3) . . . . ?
C19 O2 C20 C21 -2.3(4) . . . . ?
O3 C20 C21 C22 2.7(6) . . . . ?
O2 C20 C21 C22 -177.2(3) . . . . ?
O3 C20 C21 C11 178.7(3) . . . . ?
O2 C20 C21 C11 -1.2(4) . . . . ?
C10 C11 C21 C22 1.0(3) . . . . ?
C12 C11 C21 C22 -179.1(3) . . . . ?
C10 C11 C21 C20 -175.8(3) . . . . ?
C12 C11 C21 C20 4.1(4) . . . . ?
C4 N1 C22 N2 0.7(3) . . . . ?
C3 N1 C22 N2 177.1(3) . . . . ?
C4 N1 C22 C21 -177.0(4) . . . . ?
C3 N1 C22 C21 -0.7(6) . . . . ?
C10 N2 C22 N1 -177.2(3) . . . . ?
C9 N2 C22 N1 0.1(3) . . . . ?
C10 N2 C22 C21 1.4(3) . . . . ?
C9 N2 C22 C21 178.7(3) . . . . ?
C20 C21 C22 N1 -7.2(7) . . . . ?
C11 C21 C22 N1 176.3(4) . . . . ?
C20 C21 C22 N2 175.1(3) . . . . ?
C11 C21 C22 N2 -1.5(3) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_2f
_database_code_depnum_ccdc_archive 'CCDC 2314964'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2023-12-17 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N2 O2'
_chemical_formula_sum            'C26 H20 N2 O2'
_chemical_formula_weight         392.44

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/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                   7.3332(6)
_cell_length_b                   14.6008(14)
_cell_length_c                   18.4846(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.359(3)
_cell_angle_gamma                90
_cell_volume                     1975.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7769
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44473
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.611
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_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             3496
_reflns_number_gt                2284
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'SAINT(Bruker, 2013)'
_computing_data_reduction        'SAINT(Bruker, 2013)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.5480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0085(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3496
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.1631(2) 0.37738(11) 0.40603(9) 0.0608(5) Uani 1 1 d . . . . .
O2 O 0.0678(2) 0.45595(13) 0.30931(9) 0.0780(6) Uani 1 1 d . . . . .
N1 N 0.1049(2) 0.69358(13) 0.34271(9) 0.0510(5) Uani 1 1 d . . . . .
N2 N 0.1984(2) 0.68109(12) 0.45832(9) 0.0431(4) Uani 1 1 d . . . . .
C1 C 0.3001(4) 0.5818(2) 0.20135(13) 0.0668(7) Uani 1 1 d . . . . .
H1 H 0.231516 0.529461 0.209063 0.080 Uiso 1 1 calc R U . . .
C2 C 0.4615(4) 0.5742(2) 0.16640(14) 0.0763(8) Uani 1 1 d . . . . .
H2 H 0.500114 0.517295 0.150745 0.092 Uiso 1 1 calc R U . . .
C3 C 0.5632(4) 0.6499(2) 0.15501(15) 0.0797(8) Uani 1 1 d . . . . .
H3 H 0.672485 0.644605 0.132257 0.096 Uiso 1 1 calc R U . . .
C4 C 0.5055(4) 0.7342(2) 0.17689(15) 0.0849(9) Uani 1 1 d . . . . .
H4 H 0.574695 0.786077 0.168537 0.102 Uiso 1 1 calc R U . . .
C5 C 0.3430(4) 0.7419(2) 0.21164(14) 0.0742(8) Uani 1 1 d . . . . .
H5 H 0.303537 0.799228 0.226118 0.089 Uiso 1 1 calc R U . . .
C6 C 0.2395(3) 0.66521(19) 0.22487(11) 0.0571(6) Uani 1 1 d . . . . .
C7 C 0.0678(3) 0.67187(19) 0.26591(12) 0.0641(7) Uani 1 1 d . . . . .
H7A H -0.010684 0.718884 0.243865 0.077 Uiso 1 1 calc R U . . .
H7B H 0.002692 0.614096 0.261842 0.077 Uiso 1 1 calc R U . . .
C8 C 0.1240(3) 0.78150(17) 0.37198(12) 0.0512(6) Uani 1 1 d . . . . .
C9 C 0.0943(3) 0.8672(2) 0.34089(15) 0.0674(7) Uani 1 1 d . . . . .
H9 H 0.056934 0.873583 0.292199 0.081 Uiso 1 1 calc R U . . .
C10 C 0.1224(3) 0.94229(19) 0.38526(18) 0.0770(8) Uani 1 1 d . . . . .
H10 H 0.103073 1.000394 0.365660 0.092 Uiso 1 1 calc R U . . .
C11 C 0.1782(3) 0.93471(18) 0.45787(18) 0.0743(8) Uani 1 1 d . . . . .
H11 H 0.195635 0.987302 0.485806 0.089 Uiso 1 1 calc R U . . .
C12 C 0.2084(3) 0.84941(17) 0.48930(14) 0.0601(7) Uani 1 1 d . . . . .
H12 H 0.245455 0.843293 0.538038 0.072 Uiso 1 1 calc R U . . .
C13 C 0.1810(3) 0.77408(15) 0.44504(12) 0.0461(5) Uani 1 1 d . . . . .
C14 C 0.2477(3) 0.62264(14) 0.51521(11) 0.0427(5) Uani 1 1 d . . . . .
H14 H 0.284142 0.639712 0.562330 0.051 Uiso 1 1 calc R U . . .
C15 C 0.2328(2) 0.53534(14) 0.48914(10) 0.0394(5) Uani 1 1 d . . . . .
C16 C 0.2661(2) 0.44615(14) 0.52195(11) 0.0430(5) Uani 1 1 d . . . . .
C17 C 0.3356(3) 0.42962(15) 0.59344(12) 0.0495(6) Uani 1 1 d . . . . .
C18 C 0.3808(3) 0.50655(17) 0.64458(12) 0.0631(7) Uani 1 1 d . . . . .
H18A H 0.428922 0.482282 0.690046 0.095 Uiso 1 1 calc R U . . .
H18B H 0.272335 0.541242 0.652085 0.095 Uiso 1 1 calc R U . . .
H18C H 0.470264 0.545590 0.624494 0.095 Uiso 1 1 calc R U . . .
C19 C 0.3625(3) 0.33999(17) 0.61649(14) 0.0613(7) Uani 1 1 d . . . . .
H19 H 0.409167 0.329964 0.663695 0.074 Uiso 1 1 calc R U . . .
C20 C 0.3237(3) 0.26507(17) 0.57299(17) 0.0656(7) Uani 1 1 d . . . . .
C21 C 0.3555(4) 0.16846(17) 0.60051(19) 0.0922(10) Uani 1 1 d . . . . .
H21A H 0.484110 0.155578 0.603459 0.138 Uiso 1 1 calc R U . . .
H21B H 0.293937 0.125978 0.567836 0.138 Uiso 1 1 calc R U . . .
H21C H 0.308680 0.162533 0.647708 0.138 Uiso 1 1 calc R U . . .
C22 C 0.2553(3) 0.28116(16) 0.50277(16) 0.0635(7) Uani 1 1 d . . . . .
H22 H 0.226771 0.232075 0.472096 0.076 Uiso 1 1 calc R U . . .
C23 C 0.2290(3) 0.36992(16) 0.47793(13) 0.0509(6) Uani 1 1 d . . . . .
C24 C 0.1294(3) 0.46063(17) 0.37177(13) 0.0543(6) Uani 1 1 d . . . . .
C25 C 0.1700(3) 0.53953(15) 0.41392(11) 0.0422(5) Uani 1 1 d . . . . .
C26 C 0.1521(3) 0.63202(15) 0.39710(11) 0.0437(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C24 1.386(3) . ?
O1 C23 1.392(3) . ?
O2 C24 1.217(3) . ?
N1 C26 1.377(3) . ?
N1 C8 1.397(3) . ?
N1 C7 1.464(3) . ?
N2 C26 1.365(2) . ?
N2 C13 1.384(3) . ?
N2 C14 1.386(2) . ?
C1 C6 1.376(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.389(3) . ?
C8 C13 1.394(3) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C15 C25 1.440(3) . ?
C15 C16 1.451(3) . ?
C16 C23 1.396(3) . ?
C16 C17 1.409(3) . ?
C17 C19 1.387(3) . ?
C17 C18 1.493(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.384(4) . ?
C20 C21 1.513(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9300 . ?
C24 C25 1.413(3) . ?
C25 C26 1.390(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O1 C23 123.21(18) . . ?
C26 N1 C8 107.56(17) . . ?
C26 N1 C7 126.2(2) . . ?
C8 N1 C7 125.67(19) . . ?
C26 N2 C13 110.59(17) . . ?
C26 N2 C14 110.31(17) . . ?
C13 N2 C14 139.10(18) . . ?
C6 C1 C2 121.2(3) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 120.6(2) . . ?
C5 C6 C7 121.3(3) . . ?
N1 C7 C6 112.81(17) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 120.1(2) . . ?
C9 C8 N1 131.1(2) . . ?
C13 C8 N1 108.75(19) . . ?
C10 C9 C8 117.2(2) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C11 122.6(2) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 117.0(2) . . ?
C13 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
C12 C13 N2 132.0(2) . . ?
C12 C13 C8 122.5(2) . . ?
N2 C13 C8 105.50(19) . . ?
C15 C14 N2 107.17(17) . . ?
C15 C14 H14 126.4 . . ?
N2 C14 H14 126.4 . . ?
C14 C15 C25 108.40(18) . . ?
C14 C15 C16 133.04(19) . . ?
C25 C15 C16 118.56(18) . . ?
C23 C16 C17 117.2(2) . . ?
C23 C16 C15 116.7(2) . . ?
C17 C16 C15 126.05(19) . . ?
C19 C17 C16 119.1(2) . . ?
C19 C17 C18 119.5(2) . . ?
C16 C17 C18 121.3(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 123.3(2) . . ?
C20 C19 H19 118.3 . . ?
C17 C19 H19 118.3 . . ?
C19 C20 C22 117.6(2) . . ?
C19 C20 C21 121.4(3) . . ?
C22 C20 C21 120.9(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 C23 120.4(2) . . ?
C20 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 O1 115.1(2) . . ?
C22 C23 C16 122.3(2) . . ?
O1 C23 C16 122.6(2) . . ?
O2 C24 O1 115.5(2) . . ?
O2 C24 C25 128.6(2) . . ?
O1 C24 C25 115.9(2) . . ?
C26 C25 C24 130.9(2) . . ?
C26 C25 C15 106.14(17) . . ?
C24 C25 C15 122.9(2) . . ?
N2 C26 N1 107.59(18) . . ?
N2 C26 C25 107.97(17) . . ?
N1 C26 C25 144.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -177.2(2) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 176.9(2) . . . . ?
C26 N1 C7 C6 -83.4(3) . . . . ?
C8 N1 C7 C6 86.9(3) . . . . ?
C1 C6 C7 N1 108.8(3) . . . . ?
C5 C6 C7 N1 -69.4(3) . . . . ?
C26 N1 C8 C9 -179.9(2) . . . . ?
C7 N1 C8 C9 8.3(3) . . . . ?
C26 N1 C8 C13 -0.8(2) . . . . ?
C7 N1 C8 C13 -172.58(18) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
N1 C8 C9 C10 178.7(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 N2 179.9(2) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C26 N2 C13 C12 178.7(2) . . . . ?
C14 N2 C13 C12 -0.8(4) . . . . ?
C26 N2 C13 C8 -0.9(2) . . . . ?
C14 N2 C13 C8 179.6(2) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
N1 C8 C13 C12 -178.63(19) . . . . ?
C9 C8 C13 N2 -179.73(18) . . . . ?
N1 C8 C13 N2 1.0(2) . . . . ?
C26 N2 C14 C15 0.2(2) . . . . ?
C13 N2 C14 C15 179.8(2) . . . . ?
N2 C14 C15 C25 -0.7(2) . . . . ?
N2 C14 C15 C16 179.57(19) . . . . ?
C14 C15 C16 C23 177.8(2) . . . . ?
C25 C15 C16 C23 -1.8(3) . . . . ?
C14 C15 C16 C17 -3.5(3) . . . . ?
C25 C15 C16 C17 176.80(17) . . . . ?
C23 C16 C17 C19 -0.3(3) . . . . ?
C15 C16 C17 C19 -178.99(19) . . . . ?
C23 C16 C17 C18 179.56(19) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C19 C20 -0.4(3) . . . . ?
C18 C17 C19 C20 179.7(2) . . . . ?
C17 C19 C20 C22 0.3(3) . . . . ?
C17 C19 C20 C21 180.0(2) . . . . ?
C19 C20 C22 C23 0.5(3) . . . . ?
C21 C20 C22 C23 -179.1(2) . . . . ?
C20 C22 C23 O1 178.76(19) . . . . ?
C20 C22 C23 C16 -1.3(3) . . . . ?
C24 O1 C23 C22 -179.67(18) . . . . ?
C24 O1 C23 C16 0.4(3) . . . . ?
C17 C16 C23 C22 1.2(3) . . . . ?
C15 C16 C23 C22 179.94(18) . . . . ?
C17 C16 C23 O1 -178.86(17) . . . . ?
C15 C16 C23 O1 -0.1(3) . . . . ?
C23 O1 C24 O2 -178.29(18) . . . . ?
C23 O1 C24 C25 1.4(3) . . . . ?
O2 C24 C25 C26 0.0(4) . . . . ?
O1 C24 C25 C26 -179.55(19) . . . . ?
O2 C24 C25 C15 176.2(2) . . . . ?
O1 C24 C25 C15 -3.4(3) . . . . ?
C14 C15 C25 C26 0.9(2) . . . . ?
C16 C15 C25 C26 -179.30(16) . . . . ?
C14 C15 C25 C24 -176.01(18) . . . . ?
C16 C15 C25 C24 3.7(3) . . . . ?
C13 N2 C26 N1 0.4(2) . . . . ?
C14 N2 C26 N1 -179.90(15) . . . . ?
C13 N2 C26 C25 -179.31(16) . . . . ?
C14 N2 C26 C25 0.4(2) . . . . ?
C8 N1 C26 N2 0.2(2) . . . . ?
C7 N1 C26 N2 171.96(18) . . . . ?
C8 N1 C26 C25 179.8(3) . . . . ?
C7 N1 C26 C25 -8.5(4) . . . . ?
C24 C25 C26 N2 175.83(19) . . . . ?
C15 C25 C26 N2 -0.8(2) . . . . ?
C24 C25 C26 N1 -3.7(4) . . . . ?
C15 C25 C26 N1 179.6(3) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.033

