# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

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

data_m_398_new
_database_code_depnum_ccdc_archive 'CCDC 2246679'
loop_
_audit_author_name
_audit_author_address
Tafeenko
;MSU
Russia
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N3 O3'
_chemical_formula_sum            'C25 H21 N3 O3'
_chemical_formula_weight         411.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4900(10)
_cell_length_b                   10.2300(10)
_cell_length_c                   12.327(2)
_cell_angle_alpha                97.010(10)
_cell_angle_beta                 105.660(10)
_cell_angle_gamma                112.190(10)
_cell_volume                     1032.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1325
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      62.43

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .17
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .04
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_T_max  0.740

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            11960
_diffrn_reflns_av_unetI/netI     0.3163
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.848
_diffrn_reflns_theta_max         66.963
_diffrn_reflns_theta_full        66.963
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             11960
_reflns_number_gt                3328
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,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)+(0.0865P)²] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0046(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11960
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2301
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2523
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_restrained_S_all      0.738
_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 0.1533(7) 0.7195(6) 0.3216(6) 0.0598(18) Uani 1 1 d . . . . .
O2 O 0.9578(7) 0.9407(5) 0.6264(5) 0.0577(17) Uani 1 1 d . . . . .
O3 O 0.7629(7) 1.0108(5) 0.5511(6) 0.0620(18) Uani 1 1 d . . . . .
N1 N 0.0872(9) 0.4260(6) 0.2044(6) 0.053(2) Uani 1 1 d . . . . .
N2 N 0.0984(10) 0.2947(6) 0.1737(7) 0.054(2) Uani 1 1 d . . . . .
N3 N 0.6429(8) 0.5383(6) 0.3898(7) 0.049(2) Uani 1 1 d . . . . .
C1 C 0.2538(11) 0.3229(7) 0.2246(7) 0.043(2) Uani 1 1 d . . . . .
C2 C 0.3461(10) 0.4712(7) 0.2897(7) 0.042(2) Uani 1 1 d . . . . .
C3 C 0.5058(11) 0.5618(7) 0.3585(8) 0.048(2) Uani 1 1 d . . . . .
C4 C 0.7736(10) 0.6617(8) 0.4660(8) 0.053(2) Uani 1 1 d . . . . .
C5 C 0.7218(11) 0.7699(8) 0.4816(8) 0.053(2) Uani 1 1 d . . . . .
C6 C 0.5527(10) 0.7095(7) 0.4142(8) 0.046(2) Uani 1 1 d . . . . .
C7 C 0.4348(11) 0.7634(8) 0.4029(8) 0.051(2) Uani 1 1 d . . . . .
H7 H 0.4642 0.8582 0.4426 0.061 Uiso 1 1 calc R U . . .
C8 C 0.2780(11) 0.6779(8) 0.3345(8) 0.049(2) Uani 1 1 d . . . . .
C9 C 0.2363(9) 0.5327(7) 0.2773(7) 0.045(2) Uani 1 1 d . . . . .
C10 C 0.9330(11) 0.6579(9) 0.5119(9) 0.063(3) Uani 1 1 d . . . . .
H10A H 1.0175 0.7493 0.5160 0.094 Uiso 1 1 calc R U . . .
H10B H 0.9360 0.5807 0.4612 0.094 Uiso 1 1 calc R U . . .
H10C H 0.9486 0.6410 0.5883 0.094 Uiso 1 1 calc R U . . .
C11 C 0.8166(11) 0.9181(8) 0.5551(8) 0.049(2) Uani 1 1 d . . . . .
C12 C 1.0521(11) 1.0833(8) 0.7106(9) 0.063(3) Uani 1 1 d . . . . .
H12A H 0.9962 1.0959 0.7636 0.076 Uiso 1 1 calc R U . . .
H12B H 1.0685 1.1611 0.6709 0.076 Uiso 1 1 calc R U . . .
C13 C 1.2113(13) 1.0853(10) 0.7759(10) 0.085(3) Uani 1 1 d . . . . .
H13A H 1.1935 1.0110 0.8180 0.128 Uiso 1 1 calc R U . . .
H13B H 1.2802 1.1789 0.8295 0.128 Uiso 1 1 calc R U . . .
H13C H 1.2622 1.0672 0.7219 0.128 Uiso 1 1 calc R U . . .
C14 C -0.0649(10) 0.4260(7) 0.1534(8) 0.049(2) Uani 1 1 d . . . . .
C15 C -0.0769(12) 0.5345(8) 0.0988(9) 0.061(3) Uani 1 1 d . . . . .
H15 H 0.0157 0.6119 0.0999 0.073 Uiso 1 1 calc R U . . .
C16 C -0.2279(14) 0.5250(10) 0.0435(10) 0.076(3) Uani 1 1 d . . . . .
H16 H -0.2374 0.5977 0.0077 0.091 Uiso 1 1 calc R U . . .
C17 C -0.3669(12) 0.4086(10) 0.0398(10) 0.082(3) Uani 1 1 d . . . . .
H17 H -0.4687 0.4017 -0.0003 0.098 Uiso 1 1 calc R U . . .
C18 C -0.3529(13) 0.3031(10) 0.0963(10) 0.076(3) Uani 1 1 d . . . . .
H18 H -0.4458 0.2264 0.0957 0.091 Uiso 1 1 calc R U . . .
C19 C -0.2053(12) 0.3101(8) 0.1526(9) 0.062(3) Uani 1 1 d . . . . .
H19 H -0.1968 0.2387 0.1905 0.075 Uiso 1 1 calc R U . . .
C20 C 0.3001(10) 0.2031(8) 0.2055(8) 0.048(2) Uani 1 1 d . . . . .
C21 C 0.2189(11) 0.0956(8) 0.1027(9) 0.059(3) Uani 1 1 d . . . . .
H21 H 0.1389 0.1036 0.0445 0.070 Uiso 1 1 calc R U . . .
C22 C 0.2529(13) -0.0259(8) 0.0827(10) 0.068(3) Uani 1 1 d . . . . .
H22 H 0.1935 -0.0989 0.0139 0.081 Uiso 1 1 calc R U . . .
C23 C 0.3751(13) -0.0346(9) 0.1666(10) 0.069(3) Uani 1 1 d . . . . .
H23 H 0.4019 -0.1121 0.1531 0.083 Uiso 1 1 calc R U . . .
C24 C 0.4588(12) 0.0702(9) 0.2710(9) 0.064(3) Uani 1 1 d . . . . .
H24 H 0.5399 0.0625 0.3285 0.076 Uiso 1 1 calc R U . . .
C25 C 0.4190(11) 0.1908(7) 0.2897(8) 0.052(2) Uani 1 1 d . . . . .
H25 H 0.4747 0.2617 0.3599 0.062 Uiso 1 1 calc R U . . .
H1 H 0.168(11) 0.813(10) 0.369(9) 0.09(3) Uiso 1 1 d . . . . .
H2 H 0.671(14) 0.472(13) 0.373(11) 0.12(4) 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 C8 1.379(9) . ?
O1 H1 0.99(9) . ?
O2 C11 1.304(9) . ?
O2 C12 1.467(9) . ?
O3 C11 1.234(8) . ?
N1 C9 1.382(10) . ?
N1 N2 1.401(7) . ?
N1 C14 1.411(10) . ?
N2 C1 1.336(10) . ?
N3 C3 1.373(10) . ?
N3 C4 1.384(10) . ?
N3 H2 0.84(11) . ?
C1 C2 1.426(10) . ?
C1 C20 1.463(10) . ?
C2 C3 1.389(11) . ?
C2 C9 1.392(10) . ?
C3 C6 1.424(9) . ?
C4 C5 1.383(10) . ?
C4 C10 1.482(11) . ?
C5 C6 1.433(11) . ?
C5 C11 1.457(11) . ?
C6 C7 1.405(11) . ?
C7 C8 1.360(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 C13 1.499(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.390(11) . ?
C14 C19 1.406(11) . ?
C15 C16 1.371(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.355(12) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.369(11) . ?
C20 C21 1.379(11) . ?
C21 C22 1.407(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(13) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(13) . ?
C23 H23 0.9300 . ?
C24 C25 1.431(10) . ?
C24 H24 0.9300 . ?
C25 H25 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
C8 O1 H1 122(5) . . ?
C11 O2 C12 116.7(6) . . ?
C9 N1 N2 110.1(6) . . ?
C9 N1 C14 133.3(6) . . ?
N2 N1 C14 116.5(6) . . ?
C1 N2 N1 106.0(6) . . ?
C3 N3 C4 110.8(6) . . ?
C3 N3 H2 138(8) . . ?
C4 N3 H2 111(8) . . ?
N2 C1 C2 110.9(6) . . ?
N2 C1 C20 117.5(6) . . ?
C2 C1 C20 131.6(8) . . ?
C3 C2 C9 116.7(6) . . ?
C3 C2 C1 137.6(7) . . ?
C9 C2 C1 105.7(7) . . ?
N3 C3 C2 132.3(6) . . ?
N3 C3 C6 106.7(7) . . ?
C2 C3 C6 121.0(7) . . ?
C5 C4 N3 107.9(7) . . ?
C5 C4 C10 132.9(8) . . ?
N3 C4 C10 119.2(7) . . ?
C4 C5 C6 107.7(7) . . ?
C4 C5 C11 127.6(8) . . ?
C6 C5 C11 124.7(7) . . ?
C7 C6 C3 119.6(8) . . ?
C7 C6 C5 133.2(7) . . ?
C3 C6 C5 107.0(6) . . ?
C8 C7 C6 120.6(7) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 O1 124.6(6) . . ?
C7 C8 C9 118.3(7) . . ?
O1 C8 C9 117.0(7) . . ?
N1 C9 C2 107.2(6) . . ?
N1 C9 C8 129.2(7) . . ?
C2 C9 C8 123.6(7) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O2 124.1(7) . . ?
O3 C11 C5 121.7(8) . . ?
O2 C11 C5 114.1(6) . . ?
O2 C12 C13 106.2(6) . . ?
O2 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.4(8) . . ?
C15 C14 N1 120.5(7) . . ?
C19 C14 N1 119.0(7) . . ?
C16 C15 C14 118.6(9) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 121.1(9) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.5(9) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C19 C18 C17 120.8(9) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 119.5(9) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C25 C20 C21 118.2(7) . . ?
C25 C20 C1 121.6(8) . . ?
C21 C20 C1 120.2(8) . . ?
C20 C21 C22 122.3(9) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C21 118.7(9) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 120.8(8) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C25 119.0(9) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C20 C25 C24 120.9(8) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 N2 C1 -1.9(9) . . . . ?
C14 N1 N2 C1 175.5(8) . . . . ?
N1 N2 C1 C2 0.5(10) . . . . ?
N1 N2 C1 C20 -179.4(7) . . . . ?
N2 C1 C2 C3 179.9(10) . . . . ?
C20 C1 C2 C3 -0.3(18) . . . . ?
N2 C1 C2 C9 1.0(10) . . . . ?
C20 C1 C2 C9 -179.1(9) . . . . ?
C4 N3 C3 C2 -176.6(9) . . . . ?
C4 N3 C3 C6 2.2(9) . . . . ?
C9 C2 C3 N3 179.4(10) . . . . ?
C1 C2 C3 N3 0.7(18) . . . . ?
C9 C2 C3 C6 0.7(12) . . . . ?
C1 C2 C3 C6 -178.0(10) . . . . ?
C3 N3 C4 C5 -2.1(10) . . . . ?
C3 N3 C4 C10 178.9(9) . . . . ?
N3 C4 C5 C6 1.2(10) . . . . ?
C10 C4 C5 C6 179.9(10) . . . . ?
N3 C4 C5 C11 179.3(8) . . . . ?
C10 C4 C5 C11 -1.9(18) . . . . ?
N3 C3 C6 C7 -176.7(8) . . . . ?
C2 C3 C6 C7 2.2(12) . . . . ?
N3 C3 C6 C5 -1.4(9) . . . . ?
C2 C3 C6 C5 177.6(9) . . . . ?
C4 C5 C6 C7 174.6(9) . . . . ?
C11 C5 C6 C7 -3.6(17) . . . . ?
C4 C5 C6 C3 0.1(10) . . . . ?
C11 C5 C6 C3 -178.1(8) . . . . ?
C3 C6 C7 C8 -3.4(13) . . . . ?
C5 C6 C7 C8 -177.3(10) . . . . ?
C6 C7 C8 O1 177.4(8) . . . . ?
C6 C7 C8 C9 1.5(13) . . . . ?
N2 N1 C9 C2 2.6(9) . . . . ?
C14 N1 C9 C2 -174.3(9) . . . . ?
N2 N1 C9 C8 -175.8(9) . . . . ?
C14 N1 C9 C8 7.3(16) . . . . ?
C3 C2 C9 N1 178.7(8) . . . . ?
C1 C2 C9 N1 -2.2(9) . . . . ?
C3 C2 C9 C8 -2.8(13) . . . . ?
C1 C2 C9 C8 176.4(8) . . . . ?
C7 C8 C9 N1 179.9(9) . . . . ?
O1 C8 C9 N1 3.6(14) . . . . ?
C7 C8 C9 C2 1.7(13) . . . . ?
O1 C8 C9 C2 -174.6(8) . . . . ?
C12 O2 C11 O3 3.6(13) . . . . ?
C12 O2 C11 C5 -174.1(7) . . . . ?
C4 C5 C11 O3 170.8(9) . . . . ?
C6 C5 C11 O3 -11.3(14) . . . . ?
C4 C5 C11 O2 -11.3(14) . . . . ?
C6 C5 C11 O2 166.5(9) . . . . ?
C11 O2 C12 C13 -176.3(9) . . . . ?
C9 N1 C14 C15 47.0(14) . . . . ?
N2 N1 C14 C15 -129.7(8) . . . . ?
C9 N1 C14 C19 -136.7(10) . . . . ?
N2 N1 C14 C19 46.6(11) . . . . ?
C19 C14 C15 C16 -0.7(13) . . . . ?
N1 C14 C15 C16 175.5(9) . . . . ?
C14 C15 C16 C17 -1.0(15) . . . . ?
C15 C16 C17 C18 2.2(16) . . . . ?
C16 C17 C18 C19 -1.7(16) . . . . ?
C17 C18 C19 C14 -0.1(15) . . . . ?
C15 C14 C19 C18 1.3(14) . . . . ?
N1 C14 C19 C18 -175.0(9) . . . . ?
N2 C1 C20 C25 -146.5(9) . . . . ?
C2 C1 C20 C25 33.7(14) . . . . ?
N2 C1 C20 C21 30.7(12) . . . . ?
C2 C1 C20 C21 -149.1(9) . . . . ?
C25 C20 C21 C22 0.9(13) . . . . ?
C1 C20 C21 C22 -176.5(9) . . . . ?
C20 C21 C22 C23 -2.6(14) . . . . ?
C21 C22 C23 C24 2.9(15) . . . . ?
C22 C23 C24 C25 -1.6(14) . . . . ?
C21 C20 C25 C24 0.5(12) . . . . ?
C1 C20 C25 C24 177.8(8) . . . . ?
C23 C24 C25 C20 -0.2(13) . . . . ?

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
C7 H7 O3 0.93 2.52 3.048(10) 116.0 .
O1 H1 O3 0.99(9) 1.73(10) 2.706(7) 167(8) 2_676

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_SV-60
_database_code_depnum_ccdc_archive 'CCDC 2249815'
loop_
_audit_author_name
_audit_author_address
'Vladimir Chernyshev'
;Lomonosov Moscow State University
Russia
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_SV-60               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01512 Ang.
RESPONSE: This crystal structure has been determined and refined versus powder diffraction data.
;
# Added during the CSD deposition process: Tuesday 21 March 2023 04:41 PM
# end Validation Reply Form


_audit_creation_method           'MRIA, SHELXL-97'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N4 O3'
_chemical_formula_sum            'C25 H22 N4 O3'
_chemical_formula_weight         426.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7488(12)
_cell_length_b                   10.0324(15)
_cell_length_c                   12.6387(18)
_cell_angle_alpha                96.046(17)
_cell_angle_beta                 105.086(19)
_cell_angle_gamma                112.80(2)
_cell_volume                     1070.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1107
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      37.51

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              15 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              1 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              1 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 
thin layer on the non-diffracting silicon plate
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet # options are 'cylinder',
# 'flat_sheet' or 'irregular'

_pd_char_particle_morphology     needles
_pd_char_colour                  colorless # use ICDD colour descriptions

# The following three fields describe the preparation of the specimen. 
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.



_pd_prep_cool_rate               ?
_pd_prep_pressure                101
_pd_prep_temperature             295(2)


_exptl_special_details           
; 
 ? 
;

# This following item is used to identify the equipment used to record the
# powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
;
A.N.Frumkin Institute of Physical Chemistry and Electrochemistry RAS,
Moscow
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Fine focus X-ray tube'
_diffrn_source_target            Cu

_diffrn_radiation_source         'line-focus sealed tube'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       Empyrean
_diffrn_detector_type            ?



_diffrn_reflns_number            ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?


_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;
# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        4119
_pd_meas_2theta_range_min        5.000
_pd_meas_2theta_range_max        75.006
_pd_meas_2theta_range_inc        0.017

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

# The following fields are used to identify the programs used.

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'simulated annealing (Zhukov et al., 2001)'
_computing_structure_refinement  MRIA
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'MRIA, SHELXL97 (Sheldrick, 2008)'

#==============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text
_pd_proc_ls_profile_function     'split-type pseudo-Voigt (Toraya, 1986)'
_pd_proc_ls_pref_orient_corr     
;
Spherical harmonics expansion up to the 4th order
with 14 variables.
;
_pd_proc_ls_background_function  'Chebyshev polynomial up to the 5th order'

_pd_proc_ls_prof_R_factor        0.0407
_pd_proc_ls_prof_wR_factor       0.0577
_pd_proc_ls_prof_wR_expected     0.0234

_refine_special_details          
; 
?
;

_refine_ls_R_I_factor            0.0619
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      sigma
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     179
_refine_ls_number_restraints     122
_refine_ls_number_constraints    0

# The following item is the same as CHI, the square root of 'CHI squared = 6.106'
_refine_ls_goodness_of_fit_all   2.471

_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/su_max          .003
_refine_ls_shift/su_mean         .001


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.
_pd_proc_2theta_range_min        5.000
_pd_proc_2theta_range_max        75.006
_pd_proc_2theta_range_inc        0.017

_pd_proc_wavelength              1.5418

_pd_block_diffractogram_id       SV-60_pattern # The id used for the block
# containing the powder 
# pattern profile (section 11).

# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   none
_pd_proc_info_data_reduction     ?

#==============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8372(7) 0.2727(6) 0.6779(5) 0.081(4) Uiso 1 1 d . . .
H1 H 0.8005 0.1849 0.6460 0.122 Uiso 1 1 calc . . .
O2 O 0.0732(7) 0.0699(7) 0.3623(5) 0.079(4) Uiso 1 1 d . . .
O3 O 0.2311(7) -0.0147(7) 0.4618(5) 0.083(4) Uiso 1 1 d . . .
N1 N 0.9074(8) 0.5685(8) 0.7913(6) 0.076(4) Uiso 1 1 d . . .
N2 N 0.9006(9) 0.7012(8) 0.8298(6) 0.075(4) Uiso 1 1 d . . .
N3 N 0.3720(8) 0.4759(9) 0.6113(6) 0.081(4) Uiso 1 1 d . . .
H3 H 0.3716 0.5595 0.6343 0.097 Uiso 1 1 calc . . .
N4 N 0.6270(9) 1.1803(8) 0.8704(6) 0.088(5) Uiso 1 1 d . . .
H4A H 0.5579 1.1943 0.8208 0.106 Uiso 1 1 calc . . .
H4B H 0.6778 1.2421 0.9349 0.106 Uiso 1 1 calc . . .
C1 C 0.7534(11) 0.6804(11) 0.7793(8) 0.086(6) Uiso 1 1 d . . .
C2 C 0.6591(10) 0.5330(10) 0.7088(8) 0.090(6) Uiso 1 1 d . . .
C3 C 0.5033(11) 0.4468(10) 0.6400(8) 0.084(6) Uiso 1 1 d . . .
C4 C 0.2421(11) 0.3518(11) 0.5406(9) 0.089(6) Uiso 1 1 d . . .
C5 C 0.2887(10) 0.2408(10) 0.5196(8) 0.079(6) Uiso 1 1 d . . .
C6 C 0.4540(11) 0.2979(10) 0.5821(8) 0.083(6) Uiso 1 1 d . . .
C7 C 0.5618(11) 0.2322(11) 0.5955(8) 0.092(6) Uiso 1 1 d . . .
H7 H 0.5278 0.1327 0.5625 0.110 Uiso 1 1 calc . . .
C8 C 0.7177(11) 0.3198(11) 0.6586(9) 0.084(5) Uiso 1 1 d . . .
C9 C 0.7643(11) 0.4678(11) 0.7176(8) 0.083(6) Uiso 1 1 d . . .
C10 C 0.0898(11) 0.3667(12) 0.5037(9) 0.093(5) Uiso 1 1 d . . .
H10A H 0.1067 0.4643 0.5379 0.140 Uiso 1 1 calc . . .
H10B H 0.0121 0.2936 0.5265 0.140 Uiso 1 1 calc . . .
H10C H 0.0536 0.3516 0.4232 0.140 Uiso 1 1 calc . . .
C11 C 0.1940(10) 0.0881(10) 0.4510(8) 0.088(6) Uiso 1 1 d . . .
C12 C -0.0379(11) -0.0827(10) 0.3059(8) 0.090(6) Uiso 1 1 d . . .
H12A H -0.0679 -0.1391 0.3605 0.108 Uiso 1 1 calc . . .
H12B H 0.0089 -0.1296 0.2646 0.108 Uiso 1 1 calc . . .
C13 C -0.1813(10) -0.0774(10) 0.2255(8) 0.094(6) Uiso 1 1 d . . .
H13A H -0.2579 -0.1767 0.1864 0.141 Uiso 1 1 calc . . .
H13B H -0.1500 -0.0213 0.1720 0.141 Uiso 1 1 calc . . .
H13C H -0.2264 -0.0308 0.2674 0.141 Uiso 1 1 calc . . .
C14 C 1.0565(11) 0.5664(11) 0.8323(8) 0.091(6) Uiso 1 1 d . . .
C15 C 1.0652(11) 0.4570(10) 0.8915(9) 0.095(6) Uiso 1 1 d . . .
H15 H 0.9772 0.3908 0.9050 0.114 Uiso 1 1 calc . . .
C16 C 1.2107(11) 0.4513(11) 0.9293(8) 0.089(6) Uiso 1 1 d . . .
H16 H 1.2175 0.3739 0.9614 0.107 Uiso 1 1 calc . . .
C17 C 1.3454(10) 0.5605(11) 0.9193(8) 0.096(6) Uiso 1 1 d . . .
H17 H 1.4421 0.5581 0.9488 0.115 Uiso 1 1 calc . . .
C18 C 1.3377(11) 0.6730(11) 0.8659(9) 0.101(6) Uiso 1 1 d . . .
H18 H 1.4281 0.7443 0.8586 0.121 Uiso 1 1 calc . . .
C19 C 1.1928(11) 0.6777(11) 0.8234(8) 0.093(6) Uiso 1 1 d . . .
H19 H 1.1864 0.7539 0.7894 0.112 Uiso 1 1 calc . . .
C20 C 0.7165(11) 0.8071(11) 0.8037(8) 0.089(6) Uiso 1 1 d . . .
C21 C 0.7963(11) 0.9094(10) 0.9064(8) 0.097(6) Uiso 1 1 d . . .
H21 H 0.8727 0.8968 0.9606 0.116 Uiso 1 1 calc . . .
C22 C 0.7637(12) 1.0322(11) 0.9302(8) 0.106(6) Uiso 1 1 d . . .
H22 H 0.8129 1.0962 1.0013 0.127 Uiso 1 1 calc . . .
C23 C 0.6568(10) 1.0574(10) 0.8463(9) 0.095(6) Uiso 1 1 d . . .
C24 C 0.5751(12) 0.9562(11) 0.7418(9) 0.102(6) Uiso 1 1 d . . .
H24 H 0.5021 0.9705 0.6859 0.122 Uiso 1 1 calc . . .
C25 C 0.6071(11) 0.8317(10) 0.7239(9) 0.107(6) Uiso 1 1 d . . .
H25 H 0.5519 0.7628 0.6551 0.128 Uiso 1 1 calc . . .

_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 C8 1.394(14) . ?
O1 H1 0.8200 . ?
O2 C11 1.334(11) . ?
O2 C12 1.452(9) . ?
O3 C11 1.227(14) . ?
N1 C9 1.367(10) . ?
N1 N2 1.401(13) . ?
N1 C14 1.420(14) . ?
N2 C1 1.331(13) . ?
N3 C4 1.381(10) . ?
N3 C3 1.388(15) . ?
N3 H3 0.8601 . ?
N4 C23 1.394(15) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8601 . ?
C1 C2 1.438(12) . ?
C1 C20 1.473(18) . ?
C2 C3 1.395(11) . ?
C2 C9 1.403(17) . ?
C3 C6 1.424(14) . ?
C4 C5 1.382(17) . ?
C4 C10 1.507(17) . ?
C5 C6 1.441(13) . ?
C5 C11 1.469(12) . ?
C6 C7 1.427(17) . ?
C7 C8 1.380(12) . ?
C7 H7 0.9299 . ?
C8 C9 1.426(15) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9599 . ?
C12 C13 1.523(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9699 . ?
C13 H13A 0.9601 . ?
C13 H13B 0.9599 . ?
C13 H13C 0.9599 . ?
C14 C19 1.407(14) . ?
C14 C15 1.408(16) . ?
C15 C16 1.400(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(17) . ?
C17 H17 0.9300 . ?
C18 C19 1.396(16) . ?
C18 H18 0.9300 . ?
C19 H19 0.9301 . ?
C20 C25 1.383(16) . ?
C20 C21 1.385(12) . ?
C21 C22 1.408(18) . ?
C21 H21 0.9301 . ?
C22 C23 1.400(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(13) . ?
C24 C25 1.410(17) . ?
C24 H24 0.9300 . ?
C25 H25 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
C8 O1 H1 109.5 . . ?
C11 O2 C12 116.0(8) . . ?
C9 N1 N2 110.5(9) . . ?
C9 N1 C14 133.6(9) . . ?
N2 N1 C14 115.9(6) . . ?
C1 N2 N1 105.9(7) . . ?
C4 N3 C3 110.5(9) . . ?
C4 N3 H3 124.8 . . ?
C3 N3 H3 124.8 . . ?
C23 N4 H4A 120.0 . . ?
C23 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N2 C1 C2 111.3(10) . . ?
N2 C1 C20 116.6(7) . . ?
C2 C1 C20 132.1(9) . . ?
C3 C2 C9 117.5(9) . . ?
C3 C2 C1 138.1(11) . . ?
C9 C2 C1 104.4(8) . . ?
N3 C3 C2 132.6(10) . . ?
N3 C3 C6 106.6(7) . . ?
C2 C3 C6 120.8(11) . . ?
N3 C4 C5 108.3(9) . . ?
N3 C4 C10 116.3(10) . . ?
C5 C4 C10 135.4(8) . . ?
C4 C5 C6 107.7(7) . . ?
C4 C5 C11 129.2(9) . . ?
C6 C5 C11 123.1(10) . . ?
C3 C6 C7 120.7(8) . . ?
C3 C6 C5 106.8(10) . . ?
C7 C6 C5 132.4(8) . . ?
C8 C7 C6 118.4(9) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 O1 125.2(9) . . ?
C7 C8 C9 119.8(11) . . ?
O1 C8 C9 114.8(7) . . ?
N1 C9 C2 107.9(9) . . ?
N1 C9 C8 129.6(11) . . ?
C2 C9 C8 122.5(8) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O2 119.5(8) . . ?
O3 C11 C5 124.3(8) . . ?
O2 C11 C5 115.4(10) . . ?
O2 C12 C13 106.9(8) . . ?
O2 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 121.2(10) . . ?
C19 C14 N1 121.2(10) . . ?
C15 C14 N1 117.4(9) . . ?
C16 C15 C14 117.8(9) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C17 C16 C15 120.6(10) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 121.1(10) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.3(9) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C14 119.6(11) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C25 C20 C21 117.9(11) . . ?
C25 C20 C1 121.5(8) . . ?
C21 C20 C1 120.6(10) . . ?
C20 C21 C22 121.1(10) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 119.7(9) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N4 C23 C24 120.5(10) . . ?
N4 C23 C22 119.1(8) . . ?
C24 C23 C22 120.3(11) . . ?
C23 C24 C25 117.8(10) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
C20 C25 C24 123.2(9) . . ?
C20 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?

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

O1 H1 O3 0.82 1.94 2.711(9) 157 2_656

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.274
