# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_Pr37
_database_code_depnum_ccdc_archive 'CCDC 2350931'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 Cl N2 O'
_chemical_formula_weight         310.77

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'
Cl Cl 0.1484 0.1585 '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                   18.3294(19)
_cell_length_b                   14.7101(15)
_cell_length_c                   5.7414(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.577(6)
_cell_angle_gamma                90
_cell_volume                     1545.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1351
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      22.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14964
_diffrn_reflns_av_unetI/netI     0.1098
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.303
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3539
_reflns_number_gt                1398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3539
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1804
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_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
Cl1 Cl 0.93785(5) 0.37416(8) -0.1245(2) 0.0829(4) Uani 1 1 d . . . . .
O1 O 0.32713(12) 0.38861(16) 0.8107(3) 0.0567(7) Uani 1 1 d . . . . .
N1 N 0.63144(16) 0.3852(2) 0.1419(5) 0.0522(8) Uani 1 1 d . . . . .
H1 H 0.6110(19) 0.436(2) 0.125(6) 0.063 Uiso 1 1 d . U . . .
N2 N 0.40430(16) 0.3881(2) 0.8310(5) 0.0624(8) Uani 1 1 d . . . . .
C3 C 0.42490(18) 0.3717(2) 0.6208(5) 0.0479(8) Uani 1 1 d . . . . .
C4 C 0.36405(17) 0.3612(2) 0.4591(6) 0.0502(9) Uani 1 1 d . . . . .
H4A H 0.364807 0.348748 0.300453 0.060 Uiso 1 1 calc R U . . .
C5 C 0.30483(18) 0.3729(2) 0.5831(5) 0.0422(8) Uani 1 1 d . . . . .
C11 C 0.60987(18) 0.3405(2) 0.3522(6) 0.0540(9) Uani 1 1 d . . . . .
H11A H 0.637046 0.366459 0.486596 0.065 Uiso 1 1 calc R U . . .
H11B H 0.621959 0.276409 0.345214 0.065 Uiso 1 1 calc R U . . .
C12 C 0.53039(18) 0.3506(2) 0.3811(6) 0.0530(9) Uani 1 1 d . . . . .
H12A H 0.498601 0.344854 0.249239 0.064 Uiso 1 1 calc R U . . .
C13 C 0.50220(18) 0.3673(2) 0.5814(6) 0.0552(9) Uani 1 1 d . . . . .
H13A H 0.534760 0.377071 0.709754 0.066 Uiso 1 1 calc R U . . .
C14 C 0.22619(18) 0.3742(2) 0.5289(5) 0.0428(8) Uani 1 1 d . . . . .
C15 C 0.1791(2) 0.4140(2) 0.6794(6) 0.0503(9) Uani 1 1 d . . . . .
H15A H 0.197631 0.438062 0.820692 0.060 Uiso 1 1 calc R U . . .
C16 C 0.1055(2) 0.4181(3) 0.6217(6) 0.0587(10) Uani 1 1 d . . . . .
H16A H 0.074498 0.445449 0.723182 0.070 Uiso 1 1 calc R U . . .
C17 C 0.0771(2) 0.3818(3) 0.4126(7) 0.0643(10) Uani 1 1 d . . . . .
H17A H 0.027110 0.384328 0.373497 0.077 Uiso 1 1 calc R U . . .
C18 C 0.1231(2) 0.3421(3) 0.2645(6) 0.0628(10) Uani 1 1 d . . . . .
H18A H 0.103916 0.317059 0.125080 0.075 Uiso 1 1 calc R U . . .
C19 C 0.1974(2) 0.3386(2) 0.3180(6) 0.0550(9) Uani 1 1 d . . . . .
H19A H 0.228154 0.312489 0.213791 0.066 Uiso 1 1 calc R U . . .
C21 C 0.70494(17) 0.3835(2) 0.0880(5) 0.0426(8) Uani 1 1 d . . . . .
C22 C 0.72581(19) 0.4288(2) -0.1111(5) 0.0496(9) Uani 1 1 d . . . . .
H22A H 0.691118 0.461446 -0.201664 0.060 Uiso 1 1 calc R U . . .
C23 C 0.7967(2) 0.4258(2) -0.1754(6) 0.0513(9) Uani 1 1 d . . . . .
H23A H 0.809548 0.456120 -0.308844 0.062 Uiso 1 1 calc R U . . .
C24 C 0.84810(18) 0.3784(2) -0.0438(6) 0.0504(8) Uani 1 1 d . . . . .
C25 C 0.82962(19) 0.3338(2) 0.1553(6) 0.0539(9) Uani 1 1 d . . . . .
H25A H 0.865134 0.302706 0.246452 0.065 Uiso 1 1 calc R U . . .
C26 C 0.75796(18) 0.3355(2) 0.2191(5) 0.0496(9) Uani 1 1 d . . . . .
H26A H 0.745332 0.303999 0.351183 0.060 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
Cl1 C24 1.738(3) . ?
O1 C5 1.364(3) . ?
O1 N2 1.412(3) . ?
N1 C21 1.401(4) . ?
N1 C11 1.451(4) . ?
N1 H1 0.84(3) . ?
N2 C3 1.310(4) . ?
C3 C4 1.414(4) . ?
C3 C13 1.450(4) . ?
C4 C5 1.346(4) . ?
C4 H4A 0.9300 . ?
C5 C14 1.456(4) . ?
C11 C12 1.484(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.313(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.388(4) . ?
C14 C19 1.393(4) . ?
C15 C16 1.370(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.365(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.379(5) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C21 C26 1.386(4) . ?
C21 C22 1.396(4) . ?
C22 C23 1.373(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.362(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.379(4) . ?
C25 C26 1.386(4) . ?
C25 H25A 0.9300 . ?
C26 H26A 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
C5 O1 N2 108.5(2) . . ?
C21 N1 C11 119.5(3) . . ?
C21 N1 H1 115(2) . . ?
C11 N1 H1 111(2) . . ?
C3 N2 O1 105.6(2) . . ?
N2 C3 C4 111.4(3) . . ?
N2 C3 C13 119.5(3) . . ?
C4 C3 C13 129.1(3) . . ?
C5 C4 C3 105.5(3) . . ?
C5 C4 H4A 127.2 . . ?
C3 C4 H4A 127.2 . . ?
C4 C5 O1 109.0(3) . . ?
C4 C5 C14 135.2(3) . . ?
O1 C5 C14 115.8(2) . . ?
N1 C11 C12 111.6(3) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 124.0(3) . . ?
C13 C12 H12A 118.0 . . ?
C11 C12 H12A 118.0 . . ?
C12 C13 C3 125.9(3) . . ?
C12 C13 H13A 117.0 . . ?
C3 C13 H13A 117.0 . . ?
C15 C14 C19 118.9(3) . . ?
C15 C14 C5 121.3(3) . . ?
C19 C14 C5 119.8(3) . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C18 C19 C14 119.6(3) . . ?
C18 C19 H19A 120.2 . . ?
C14 C19 H19A 120.2 . . ?
C26 C21 C22 118.0(3) . . ?
C26 C21 N1 122.7(3) . . ?
C22 C21 N1 119.3(3) . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22A 119.4 . . ?
C21 C22 H22A 119.4 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 Cl1 120.3(3) . . ?
C25 C24 Cl1 119.3(3) . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25A 120.1 . . ?
C26 C25 H25A 120.1 . . ?
C25 C26 C21 120.6(3) . . ?
C25 C26 H26A 119.7 . . ?
C21 C26 H26A 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 N2 C3 -0.6(3) . . . . ?
O1 N2 C3 C4 0.0(4) . . . . ?
O1 N2 C3 C13 179.7(3) . . . . ?
N2 C3 C4 C5 0.5(4) . . . . ?
C13 C3 C4 C5 -179.1(3) . . . . ?
C3 C4 C5 O1 -0.9(4) . . . . ?
C3 C4 C5 C14 177.7(3) . . . . ?
N2 O1 C5 C4 0.9(3) . . . . ?
N2 O1 C5 C14 -177.9(3) . . . . ?
C21 N1 C11 C12 179.2(3) . . . . ?
N1 C11 C12 C13 -139.0(4) . . . . ?
C11 C12 C13 C3 -175.7(3) . . . . ?
N2 C3 C13 C12 179.3(3) . . . . ?
C4 C3 C13 C12 -1.1(6) . . . . ?
C4 C5 C14 C15 -160.7(4) . . . . ?
O1 C5 C14 C15 17.8(4) . . . . ?
C4 C5 C14 C19 16.5(6) . . . . ?
O1 C5 C14 C19 -165.0(3) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C5 C14 C15 C16 177.3(3) . . . . ?
C14 C15 C16 C17 0.6(5) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C17 C18 C19 C14 1.4(5) . . . . ?
C15 C14 C19 C18 -1.0(5) . . . . ?
C5 C14 C19 C18 -178.3(3) . . . . ?
C11 N1 C21 C26 4.6(5) . . . . ?
C11 N1 C21 C22 -178.2(3) . . . . ?
C26 C21 C22 C23 0.0(5) . . . . ?
N1 C21 C22 C23 -177.3(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C22 C23 C24 C25 -0.5(5) . . . . ?
C22 C23 C24 Cl1 179.9(2) . . . . ?
C23 C24 C25 C26 1.4(5) . . . . ?
Cl1 C24 C25 C26 -178.9(3) . . . . ?
C24 C25 C26 C21 -1.7(5) . . . . ?
C22 C21 C26 C25 1.0(5) . . . . ?
N1 C21 C26 C25 178.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2 0.84(3) 2.62(4) 3.404(4) 157(3) 3_666 yes

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.048


# start Validation Reply Form
_vrf_PLAT910_Pr37                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 12 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_A64
_database_code_depnum_ccdc_archive 'CCDC 2350933'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Cl N2 O2'
_chemical_formula_weight         378.84

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   40.8182(17)
_cell_length_b                   6.3454(3)
_cell_length_c                   14.8844(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.250(2)
_cell_angle_gamma                90
_cell_volume                     3661.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1333
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      22.40

_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14340
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.038
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4194
_reflns_number_gt                1765
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0769P)²+1.2830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4194
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1620
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1902
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.011
_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
Cl1 Cl 0.48374(3) 0.8574(2) 0.61364(11) 0.1324(6) Uani 1 1 d . . . . .
O1 O 0.79152(6) 0.3956(4) 0.58485(16) 0.0737(7) Uani 1 1 d . . . . .
O2 O 0.62141(6) 0.3255(4) 0.56611(18) 0.0834(7) Uani 1 1 d . . . . .
N6 N 0.62670(6) 0.6619(4) 0.62910(17) 0.0596(7) Uani 1 1 d . . . . .
N9 N 0.72943(7) 0.4617(4) 0.59579(17) 0.0624(7) Uani 1 1 d . . . . .
H9A H 0.743411 0.373757 0.583185 0.075 Uiso 1 1 calc R U . . .
C2 C 0.79916(8) 0.5812(5) 0.6142(2) 0.0569(8) Uani 1 1 d . . . . .
C3A C 0.74149(8) 0.6560(5) 0.6272(2) 0.0554(8) Uani 1 1 d . . . . .
C3 C 0.77452(7) 0.7140(5) 0.63726(19) 0.0597(8) Uani 1 1 d . . . . .
H3A H 0.781564 0.848122 0.660558 0.072 Uiso 1 1 calc R U . . .
C4 C 0.71555(8) 0.8082(5) 0.6426(2) 0.0681(9) Uani 1 1 d . . . . .
H4A H 0.727396 0.906932 0.691761 0.082 Uiso 1 1 calc R U . . .
H4B H 0.705582 0.888025 0.584848 0.082 Uiso 1 1 calc R U . . .
C4A C 0.68749(9) 0.7076(5) 0.6695(3) 0.0748(10) Uani 1 1 d . . . . .
H4AA H 0.696854 0.667800 0.736263 0.090 Uiso 1 1 calc R U . . .
C5 C 0.65366(7) 0.8259(5) 0.6571(2) 0.0611(8) Uani 1 1 d . . . . .
H5A H 0.653799 0.892527 0.715908 0.073 Uiso 1 1 calc R U . . .
H5B H 0.649993 0.932978 0.608491 0.073 Uiso 1 1 calc R U . . .
C7A C 0.67516(8) 0.5111(5) 0.6146(2) 0.0582(8) Uani 1 1 d . . . . .
C7 C 0.63847(9) 0.4796(5) 0.5997(2) 0.0628(8) Uani 1 1 d . . . . .
C8 C 0.69609(8) 0.3972(5) 0.5829(2) 0.0631(9) Uani 1 1 d . . . . .
H8A H 0.688273 0.271518 0.551295 0.076 Uiso 1 1 calc R U . . .
C11 C 0.59245(8) 0.7065(5) 0.6245(2) 0.0586(8) Uani 1 1 d . . . . .
C12 C 0.56768(9) 0.5495(6) 0.6108(3) 0.0788(10) Uani 1 1 d . . . . .
H12A H 0.573607 0.410318 0.603775 0.095 Uiso 1 1 calc R U . . .
C13 C 0.53448(9) 0.5975(6) 0.6076(3) 0.0816(11) Uani 1 1 d . . . . .
H13A H 0.518085 0.490943 0.597423 0.098 Uiso 1 1 calc R U . . .
C14 C 0.52551(9) 0.7978(7) 0.6190(3) 0.0808(10) Uani 1 1 d . . . . .
C15 C 0.54973(10) 0.9536(6) 0.6337(3) 0.1072(15) Uani 1 1 d . . . . .
H15A H 0.543708 1.091937 0.642028 0.129 Uiso 1 1 calc R U . . .
C16 C 0.58281(9) 0.9075(6) 0.6364(3) 0.0870(12) Uani 1 1 d . . . . .
H16A H 0.598983 1.015400 0.646586 0.104 Uiso 1 1 calc R U . . .
C21 C 0.83407(8) 0.6611(5) 0.62269(19) 0.0556(8) Uani 1 1 d . . . . .
C22 C 0.84466(9) 0.8666(5) 0.6469(2) 0.0663(9) Uani 1 1 d . . . . .
H22A H 0.829401 0.962820 0.659160 0.080 Uiso 1 1 calc R U . . .
C23 C 0.87768(9) 0.9299(6) 0.6531(2) 0.0745(10) Uani 1 1 d . . . . .
H23A H 0.884265 1.068413 0.669846 0.089 Uiso 1 1 calc R U . . .
C24 C 0.90122(9) 0.7926(6) 0.6350(2) 0.0703(9) Uani 1 1 d . . . . .
C25 C 0.89041(9) 0.5917(6) 0.6095(3) 0.0808(11) Uani 1 1 d . . . . .
H25A H 0.905493 0.496967 0.595466 0.097 Uiso 1 1 calc R U . . .
C26 C 0.85785(9) 0.5258(6) 0.6041(2) 0.0712(9) Uani 1 1 d . . . . .
H26A H 0.851556 0.386787 0.587607 0.085 Uiso 1 1 calc R U . . .
C27 C 0.93704(9) 0.8650(7) 0.6416(3) 0.0931(12) Uani 1 1 d . . . . .
H27A H 0.944225 0.797412 0.593152 0.140 Uiso 1 1 calc R U . . .
H27B H 0.952688 0.828565 0.702551 0.140 Uiso 1 1 calc R U . . .
H27C H 0.937054 1.014977 0.633271 0.140 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
Cl1 C14 1.724(4) . ?
O1 C2 1.261(4) . ?
O2 C7 1.214(4) . ?
N6 C7 1.375(4) . ?
N6 C11 1.406(4) . ?
N6 C5 1.477(4) . ?
N9 C3A 1.355(4) . ?
N9 C8 1.375(4) . ?
N9 H9A 0.8600 . ?
C2 C3 1.434(4) . ?
C2 C21 1.480(4) . ?
C3A C3 1.360(4) . ?
C3A C4 1.503(4) . ?
C3 H3A 0.9300 . ?
C4 C4A 1.472(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4A C7A 1.489(4) . ?
C4A C5 1.531(4) . ?
C4A H4AA 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7A C8 1.315(4) . ?
C7A C7 1.457(4) . ?
C8 H8A 0.9300 . ?
C11 C16 1.363(4) . ?
C11 C12 1.388(4) . ?
C12 C13 1.375(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.348(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.366(5) . ?
C15 C16 1.370(5) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C21 C22 1.385(4) . ?
C21 C26 1.387(4) . ?
C22 C23 1.382(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.385(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.363(5) . ?
C24 C27 1.506(4) . ?
C25 C26 1.371(4) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N6 C11 126.5(3) . . ?
C7 N6 C5 112.3(2) . . ?
C11 N6 C5 120.9(2) . . ?
C3A N9 C8 123.7(3) . . ?
C3A N9 H9A 118.1 . . ?
C8 N9 H9A 118.1 . . ?
O1 C2 C3 121.1(3) . . ?
O1 C2 C21 118.5(3) . . ?
C3 C2 C21 120.5(3) . . ?
N9 C3A C3 121.6(3) . . ?
N9 C3A C4 116.1(3) . . ?
C3 C3A C4 122.1(3) . . ?
C3A C3 C2 124.1(3) . . ?
C3A C3 H3A 118.0 . . ?
C2 C3 H3A 118.0 . . ?
C4A C4 C3A 114.1(3) . . ?
C4A C4 H4A 108.7 . . ?
C3A C4 H4A 108.7 . . ?
C4A C4 H4B 108.7 . . ?
C3A C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C4A C7A 111.9(3) . . ?
C4 C4A C5 120.3(3) . . ?
C7A C4A C5 102.0(3) . . ?
C4 C4A H4AA 107.4 . . ?
C7A C4A H4AA 107.4 . . ?
C5 C4A H4AA 107.4 . . ?
N6 C5 C4A 104.6(2) . . ?
N6 C5 H5A 110.8 . . ?
C4A C5 H5A 110.8 . . ?
N6 C5 H5B 110.8 . . ?
C4A C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C8 C7A C7 128.5(3) . . ?
C8 C7A C4A 120.7(3) . . ?
C7 C7A C4A 110.7(3) . . ?
O2 C7 N6 126.6(3) . . ?
O2 C7 C7A 127.0(3) . . ?
N6 C7 C7A 106.3(3) . . ?
C7A C8 N9 120.8(3) . . ?
C7A C8 H8A 119.6 . . ?
N9 C8 H8A 119.6 . . ?
C16 C11 C12 117.6(3) . . ?
C16 C11 N6 120.3(3) . . ?
C12 C11 N6 122.0(3) . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 Cl1 120.3(3) . . ?
C15 C14 Cl1 120.2(3) . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C11 C16 C15 121.2(4) . . ?
C11 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C22 C21 C26 117.0(3) . . ?
C22 C21 C2 123.9(3) . . ?
C26 C21 C2 119.1(3) . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22A 119.7 . . ?
C21 C22 H22A 119.7 . . ?
C22 C23 C24 121.8(3) . . ?
C22 C23 H23A 119.1 . . ?
C24 C23 H23A 119.1 . . ?
C25 C24 C23 117.3(3) . . ?
C25 C24 C27 121.8(3) . . ?
C23 C24 C27 121.0(3) . . ?
C24 C25 C26 121.7(3) . . ?
C24 C25 H25A 119.2 . . ?
C26 C25 H25A 119.2 . . ?
C25 C26 C21 121.7(3) . . ?
C25 C26 H26A 119.2 . . ?
C21 C26 H26A 119.2 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N9 C3A C3 -178.8(3) . . . . ?
C8 N9 C3A C4 -3.6(4) . . . . ?
N9 C3A C3 C2 1.5(5) . . . . ?
C4 C3A C3 C2 -173.4(3) . . . . ?
O1 C2 C3 C3A -2.0(5) . . . . ?
C21 C2 C3 C3A 176.9(3) . . . . ?
N9 C3A C4 C4A 30.1(4) . . . . ?
C3 C3A C4 C4A -154.8(3) . . . . ?
C3A C4 C4A C7A -41.0(4) . . . . ?
C3A C4 C4A C5 -160.5(3) . . . . ?
C7 N6 C5 C4A -15.8(3) . . . . ?
C11 N6 C5 C4A 170.8(3) . . . . ?
C4 C4A C5 N6 144.0(3) . . . . ?
C7A C4A C5 N6 19.6(3) . . . . ?
C4 C4A C7A C8 28.9(5) . . . . ?
C5 C4A C7A C8 158.7(3) . . . . ?
C4 C4A C7A C7 -148.0(3) . . . . ?
C5 C4A C7A C7 -18.2(3) . . . . ?
C11 N6 C7 O2 -1.1(5) . . . . ?
C5 N6 C7 O2 -174.0(3) . . . . ?
C11 N6 C7 C7A 177.4(3) . . . . ?
C5 N6 C7 C7A 4.4(3) . . . . ?
C8 C7A C7 O2 11.2(6) . . . . ?
C4A C7A C7 O2 -172.2(3) . . . . ?
C8 C7A C7 N6 -167.3(3) . . . . ?
C4A C7A C7 N6 9.4(4) . . . . ?
C7 C7A C8 N9 173.4(3) . . . . ?
C4A C7A C8 N9 -3.0(5) . . . . ?
C3A N9 C8 C7A -10.8(5) . . . . ?
C7 N6 C11 C16 -165.6(3) . . . . ?
C5 N6 C11 C16 6.7(5) . . . . ?
C7 N6 C11 C12 16.5(5) . . . . ?
C5 N6 C11 C12 -171.2(3) . . . . ?
C16 C11 C12 C13 1.3(5) . . . . ?
N6 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C12 C13 C14 Cl1 179.3(3) . . . . ?
C13 C14 C15 C16 0.4(7) . . . . ?
Cl1 C14 C15 C16 -178.9(3) . . . . ?
C12 C11 C16 C15 -0.9(6) . . . . ?
N6 C11 C16 C15 -178.9(4) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
O1 C2 C21 C22 174.8(3) . . . . ?
C3 C2 C21 C22 -4.1(4) . . . . ?
O1 C2 C21 C26 -4.1(4) . . . . ?
C3 C2 C21 C26 177.0(3) . . . . ?
C26 C21 C22 C23 -0.8(5) . . . . ?
C2 C21 C22 C23 -179.7(3) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C25 0.8(5) . . . . ?
C22 C23 C24 C27 179.7(3) . . . . ?
C23 C24 C25 C26 -1.5(5) . . . . ?
C27 C24 C25 C26 179.6(3) . . . . ?
C24 C25 C26 C21 1.1(6) . . . . ?
C22 C21 C26 C25 0.1(5) . . . . ?
C2 C21 C26 C25 179.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9A O1 0.86 1.96 2.624(3) 133.0 . yes
C12 H12A O2 0.93 2.26 2.861(4) 122.0 . yes

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.038


# start Validation Reply Form
_vrf_PLAT910_A64                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         13 Note  
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_ZV2112
_database_code_depnum_ccdc_archive 'CCDC 2350932'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40

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      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                   13.6337(12)
_cell_length_b                   12.0340(9)
_cell_length_c                   11.0008(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.466(5)
_cell_angle_gamma                90
_cell_volume                     1721.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1591
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      22.30

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15890
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.093
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3937
_reflns_number_gt                2003
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3937
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.19660(12) 0.20860(13) 0.65681(13) 0.0430(4) Uani 1 1 d . . . . .
O2 O 0.54447(14) 0.05595(12) 0.33500(14) 0.0505(5) Uani 1 1 d . . . . .
N2 N 0.56813(15) 0.24425(13) 0.30900(16) 0.0358(5) Uani 1 1 d . . . . .
N5 N 0.33402(15) 0.20065(15) 0.52804(17) 0.0367(5) Uani 1 1 d D . . . .
H5 H 0.2915(16) 0.1702(17) 0.5660(19) 0.044 Uiso 1 1 d D U . . .
C1A C 0.52872(17) 0.34933(16) 0.3437(2) 0.0351(5) Uani 0.509(7) 1 d . . P A 1
H1A H 0.512935 0.402269 0.271538 0.042 Uiso 0.509(7) 1 calc R U P A 1
H1B H 0.579646 0.383729 0.417969 0.042 Uiso 0.509(7) 1 calc R U P A 1
C1B C 0.52872(17) 0.34933(16) 0.3437(2) 0.0351(5) Uani 0.491(7) 1 d . . P A 2
H1C H 0.478486 0.383297 0.268541 0.042 Uiso 0.491(7) 1 calc R U P A 2
H1D H 0.585562 0.402566 0.378732 0.042 Uiso 0.491(7) 1 calc R U P A 2
C3 C 0.52551(19) 0.15336(18) 0.35018(19) 0.0385(6) Uani 1 1 d . . . . .
C3A C 0.45324(19) 0.19576(17) 0.4134(2) 0.0413(6) Uani 1 1 d . . . . .
C4 C 0.39622(18) 0.14248(17) 0.47213(19) 0.0378(6) Uani 1 1 d . . . . .
H4A H 0.397967 0.063615 0.476005 0.045 Uiso 1 1 calc R U . . .
C6 C 0.32677(18) 0.31343(17) 0.5278(2) 0.0391(6) Uani 1 1 d . . . . .
C71 C 0.4104(4) 0.3744(3) 0.4925(6) 0.0306(13) Uiso 0.509(7) 1 d . . P A 1
H71A H 0.474528 0.373600 0.564850 0.037 Uiso 0.509(7) 1 calc R U P A 1
H71B H 0.389994 0.452711 0.471492 0.037 Uiso 0.509(7) 1 calc R U P A 1
C7A C 0.4279(4) 0.3169(3) 0.3776(5) 0.0317(14) Uiso 0.509(7) 1 d . . P A 1
H7A H 0.365952 0.323226 0.301188 0.038 Uiso 0.509(7) 1 calc R U P A 1
C72 C 0.3776(5) 0.3717(4) 0.4337(6) 0.0356(14) Uiso 0.491(7) 1 d . . P A 2
H72A H 0.331301 0.365505 0.345328 0.043 Uiso 0.491(7) 1 calc R U P A 2
H72B H 0.388044 0.451561 0.455194 0.043 Uiso 0.491(7) 1 calc R U P A 2
C7B C 0.4781(5) 0.3189(4) 0.4426(6) 0.0371(15) Uiso 0.491(7) 1 d . . P A 2
H7B H 0.527090 0.328126 0.530097 0.045 Uiso 0.491(7) 1 calc R U P A 2
C11 C 0.64242(16) 0.24311(16) 0.24206(18) 0.0323(5) Uani 1 1 d . . . . .
C12 C 0.69391(19) 0.14627(18) 0.2274(2) 0.0412(6) Uani 1 1 d . . . . .
H12A H 0.680796 0.078403 0.263818 0.049 Uiso 1 1 calc R U . . .
C13 C 0.76418(18) 0.14994(19) 0.1594(2) 0.0430(6) Uani 1 1 d . . . . .
H13A H 0.798558 0.083307 0.149956 0.052 Uiso 1 1 calc R U . . .
C14 C 0.78674(17) 0.24607(19) 0.1045(2) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.73588(17) 0.34212(18) 0.1217(2) 0.0397(6) Uani 1 1 d . . . . .
H15A H 0.750431 0.410148 0.086765 0.048 Uiso 1 1 calc R U . . .
C16 C 0.66431(17) 0.34095(17) 0.1887(2) 0.0368(5) Uani 1 1 d . . . . .
H16A H 0.630033 0.407673 0.198020 0.044 Uiso 1 1 calc R U . . .
C17 C 0.86398(19) 0.2486(2) 0.0305(2) 0.0512(7) Uani 1 1 d . . . . .
H17A H 0.880214 0.325867 0.016119 0.077 Uiso 1 1 calc R U . . .
H17B H 0.834917 0.211331 -0.051686 0.077 Uiso 1 1 calc R U . . .
H17C H 0.926883 0.210124 0.079169 0.077 Uiso 1 1 calc R U . . .
C21 C 0.26219(17) 0.36708(18) 0.58121(19) 0.0369(6) Uani 1 1 d . . . . .
H21A H 0.259396 0.445875 0.575992 0.044 Uiso 1 1 calc R U . . .
C22 C 0.19793(17) 0.31244(19) 0.64503(19) 0.0369(5) Uani 1 1 d . . . . .
C23 C 0.13073(17) 0.38123(18) 0.69971(19) 0.0365(5) Uani 1 1 d . . . . .
C24 C 0.09262(18) 0.48389(18) 0.6497(2) 0.0405(6) Uani 1 1 d . . . . .
H24A H 0.111909 0.513611 0.580140 0.049 Uiso 1 1 calc R U . . .
C25 C 0.0271(2) 0.5434(2) 0.6995(2) 0.0495(7) Uani 1 1 d . . . . .
H25A H 0.000436 0.612686 0.662892 0.059 Uiso 1 1 calc R U . . .
C26 C 0.00001(19) 0.5023(2) 0.8030(2) 0.0534(7) Uani 1 1 d . . . . .
H26A H -0.044867 0.543247 0.837604 0.064 Uiso 1 1 calc R U . . .
C27 C 0.0390(2) 0.4014(2) 0.8548(2) 0.0532(7) Uani 1 1 d . . . . .
H27A H 0.021838 0.373837 0.926697 0.064 Uiso 1 1 calc R U . . .
C28 C 0.10225(18) 0.3401(2) 0.8041(2) 0.0455(6) Uani 1 1 d . . . . .
H28A H 0.126835 0.269790 0.839629 0.055 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 C22 1.257(3) . ?
O2 C3 1.223(2) . ?
N2 C3 1.377(3) . ?
N2 C11 1.420(3) . ?
N2 C1B 1.469(2) . ?
N2 C1A 1.469(2) . ?
N5 C6 1.361(3) . ?
N5 C4 1.379(3) . ?
N5 H5 0.889(15) . ?
C1A C7A 1.577(5) . ?
C1A H1A 0.9900 . ?
C1A H1B 0.9900 . ?
C1B C7B 1.498(5) . ?
C1B H1C 0.9900 . ?
C1B H1D 0.9900 . ?
C3 C3A 1.458(3) . ?
C3A C4 1.317(3) . ?
C3A C7A 1.522(5) . ?
C3A C7B 1.532(5) . ?
C4 H4A 0.9500 . ?
C6 C21 1.360(3) . ?
C6 C71 1.502(5) . ?
C6 C72 1.573(5) . ?
C71 C7A 1.522(7) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?
C7A H7A 1.0000 . ?
C72 C7B 1.487(8) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C7B H7B 1.0000 . ?
C11 C16 1.388(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.382(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.390(3) . ?
C14 C17 1.512(3) . ?
C15 C16 1.388(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C22 1.436(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.489(3) . ?
C23 C24 1.388(3) . ?
C23 C28 1.408(3) . ?
C24 C25 1.380(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25A 0.9500 . ?
C26 C27 1.378(4) . ?
C26 H26A 0.9500 . ?
C27 C28 1.374(3) . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?

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
C3 N2 C11 126.86(17) . . ?
C3 N2 C1B 112.01(18) . . ?
C11 N2 C1B 121.12(16) . . ?
C3 N2 C1A 112.01(18) . . ?
C11 N2 C1A 121.12(16) . . ?
C6 N5 C4 124.02(18) . . ?
C6 N5 H5 110.8(14) . . ?
C4 N5 H5 125.1(14) . . ?
N2 C1A C7A 105.1(2) . . ?
N2 C1A H1A 110.7 . . ?
C7A C1A H1A 110.7 . . ?
N2 C1A H1B 110.7 . . ?
C7A C1A H1B 110.7 . . ?
H1A C1A H1B 108.8 . . ?
N2 C1B C7B 105.2(2) . . ?
N2 C1B H1C 110.7 . . ?
C7B C1B H1C 110.7 . . ?
N2 C1B H1D 110.7 . . ?
C7B C1B H1D 110.7 . . ?
H1C C1B H1D 108.8 . . ?
O2 C3 N2 126.1(2) . . ?
O2 C3 C3A 127.0(2) . . ?
N2 C3 C3A 106.92(18) . . ?
C4 C3A C3 130.3(2) . . ?
C4 C3A C7A 118.2(2) . . ?
C3 C3A C7A 110.2(2) . . ?
C4 C3A C7B 119.6(2) . . ?
C3 C3A C7B 107.4(2) . . ?
C3A C4 N5 120.29(19) . . ?
C3A C4 H4A 119.9 . . ?
N5 C4 H4A 119.9 . . ?
C21 C6 N5 121.91(19) . . ?
C21 C6 C71 121.4(2) . . ?
N5 C6 C71 115.3(2) . . ?
C21 C6 C72 122.9(2) . . ?
N5 C6 C72 113.6(2) . . ?
C6 C71 C7A 108.2(4) . . ?
C6 C71 H71A 110.0 . . ?
C7A C71 H71A 110.0 . . ?
C6 C71 H71B 110.0 . . ?
C7A C71 H71B 110.0 . . ?
H71A C71 H71B 108.4 . . ?
C71 C7A C3A 107.5(4) . . ?
C71 C7A C1A 116.7(4) . . ?
C3A C7A C1A 98.8(3) . . ?
C71 C7A H7A 111.1 . . ?
C3A C7A H7A 111.1 . . ?
C1A C7A H7A 111.1 . . ?
C7B C72 C6 110.2(4) . . ?
C7B C72 H72A 109.6 . . ?
C6 C72 H72A 109.6 . . ?
C7B C72 H72B 109.6 . . ?
C6 C72 H72B 109.6 . . ?
H72A C72 H72B 108.1 . . ?
C72 C7B C1B 117.6(5) . . ?
C72 C7B C3A 105.0(4) . . ?
C1B C7B C3A 101.9(3) . . ?
C72 C7B H7B 110.6 . . ?
C1B C7B H7B 110.6 . . ?
C3A C7B H7B 110.6 . . ?
C16 C11 C12 118.7(2) . . ?
C16 C11 N2 119.26(18) . . ?
C12 C11 N2 122.02(18) . . ?
C13 C12 C11 119.4(2) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C14 C13 C12 123.0(2) . . ?
C14 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
C13 C14 C15 116.8(2) . . ?
C13 C14 C17 122.3(2) . . ?
C15 C14 C17 120.9(2) . . ?
C16 C15 C14 121.5(2) . . ?
C16 C15 H15A 119.2 . . ?
C14 C15 H15A 119.2 . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C21 C22 124.3(2) . . ?
C6 C21 H21A 117.9 . . ?
C22 C21 H21A 117.9 . . ?
O1 C22 C21 122.4(2) . . ?
O1 C22 C23 118.77(19) . . ?
C21 C22 C23 118.9(2) . . ?
C24 C23 C28 118.3(2) . . ?
C24 C23 C22 122.47(19) . . ?
C28 C23 C22 119.2(2) . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24A 119.6 . . ?
C23 C24 H24A 119.5 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25A 119.9 . . ?
C26 C25 H25A 119.9 . . ?
C27 C26 C25 119.2(2) . . ?
C27 C26 H26A 120.4 . . ?
C25 C26 H26A 120.4 . . ?
C28 C27 C26 121.1(2) . . ?
C28 C27 H27A 119.4 . . ?
C26 C27 H27A 119.4 . . ?
C27 C28 C23 120.2(2) . . ?
C27 C28 H28A 119.9 . . ?
C23 C28 H28A 119.9 . . ?

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
C3 N2 C1A C7A -17.0(3) . . . . ?
C11 N2 C1A C7A 163.7(3) . . . . ?
C3 N2 C1B C7B 15.2(4) . . . . ?
C11 N2 C1B C7B -164.1(3) . . . . ?
C11 N2 C3 O2 -0.5(4) . . . . ?
C1B N2 C3 O2 -179.7(2) . . . . ?
C1A N2 C3 O2 -179.7(2) . . . . ?
C11 N2 C3 C3A -179.79(18) . . . . ?
C1B N2 C3 C3A 1.0(2) . . . . ?
C1A N2 C3 C3A 1.0(2) . . . . ?
O2 C3 C3A C4 3.2(4) . . . . ?
N2 C3 C3A C4 -177.4(2) . . . . ?
O2 C3 C3A C7A -162.8(3) . . . . ?
N2 C3 C3A C7A 16.6(3) . . . . ?
O2 C3 C3A C7B 164.1(3) . . . . ?
N2 C3 C3A C7B -16.6(3) . . . . ?
C3 C3A C4 N5 178.7(2) . . . . ?
C7A C3A C4 N5 -16.3(4) . . . . ?
C7B C3A C4 N5 19.8(4) . . . . ?
C6 N5 C4 C3A -0.2(3) . . . . ?
C4 N5 C6 C21 178.2(2) . . . . ?
C4 N5 C6 C71 -15.2(4) . . . . ?
C4 N5 C6 C72 12.2(4) . . . . ?
C21 C6 C71 C7A -149.1(3) . . . . ?
N5 C6 C71 C7A 44.2(5) . . . . ?
C6 C71 C7A C3A -56.6(6) . . . . ?
C6 C71 C7A C1A -166.3(3) . . . . ?
C4 C3A C7A C71 45.3(5) . . . . ?
C3 C3A C7A C71 -146.7(4) . . . . ?
C4 C3A C7A C1A 167.0(2) . . . . ?
C3 C3A C7A C1A -25.1(4) . . . . ?
N2 C1A C7A C71 139.1(4) . . . . ?
N2 C1A C7A C3A 24.4(3) . . . . ?
C21 C6 C72 C7B 151.2(4) . . . . ?
N5 C6 C72 C7B -42.9(6) . . . . ?
C6 C72 C7B C1B 169.2(3) . . . . ?
C6 C72 C7B C3A 56.9(6) . . . . ?
N2 C1B C7B C72 -137.6(5) . . . . ?
N2 C1B C7B C3A -23.5(4) . . . . ?
C4 C3A C7B C72 -48.6(6) . . . . ?
C3 C3A C7B C72 148.1(4) . . . . ?
C4 C3A C7B C1B -171.8(3) . . . . ?
C3 C3A C7B C1B 24.9(4) . . . . ?
C3 N2 C11 C16 169.1(2) . . . . ?
C1B N2 C11 C16 -11.8(3) . . . . ?
C1A N2 C11 C16 -11.8(3) . . . . ?
C3 N2 C11 C12 -10.5(3) . . . . ?
C1B N2 C11 C12 168.68(19) . . . . ?
C1A N2 C11 C12 168.68(19) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
N2 C11 C12 C13 178.91(19) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C12 C13 C14 C17 179.9(2) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C17 C14 C15 C16 179.6(2) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
N2 C11 C16 C15 -179.40(19) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
N5 C6 C21 C22 1.6(3) . . . . ?
C71 C6 C21 C22 -164.2(3) . . . . ?
C72 C6 C21 C22 166.3(4) . . . . ?
C6 C21 C22 O1 0.1(3) . . . . ?
C6 C21 C22 C23 179.9(2) . . . . ?
O1 C22 C23 C24 -151.8(2) . . . . ?
C21 C22 C23 C24 28.4(3) . . . . ?
O1 C22 C23 C28 26.6(3) . . . . ?
C21 C22 C23 C28 -153.2(2) . . . . ?
C28 C23 C24 C25 -1.1(3) . . . . ?
C22 C23 C24 C25 177.3(2) . . . . ?
C23 C24 C25 C26 1.5(4) . . . . ?
C24 C25 C26 C27 -0.2(4) . . . . ?
C25 C26 C27 C28 -1.4(4) . . . . ?
C26 C27 C28 C23 1.8(4) . . . . ?
C24 C23 C28 C27 -0.5(3) . . . . ?
C22 C23 C28 C27 -179.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O1 0.889(15) 1.913(18) 2.668(2) 141.7(19) . yes

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.042


# start Validation Reply Form
_vrf_PLAT201_ZV2112              
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 2 Report
RESPONSE: Disordered atoms.
;
_vrf_PLAT230_ZV2112              
;
PROBLEM: Hirshfeld Test Diff for C6 --C21 . 7.3 s.u.
RESPONSE: C6 is in contact with disordered atoms C71-C72.
;
_vrf_PLAT910_ZV2112              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 14 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_P67
_database_code_depnum_ccdc_archive 'CCDC 2350934'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 F3 N2 O2'
_chemical_formula_weight         412.40

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'
F F 0.0171 0.0103 '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                   5.4100(14)
_cell_length_b                   27.059(7)
_cell_length_c                   13.460(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.408(18)
_cell_angle_gamma                90
_cell_volume                     1958.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    347
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      12.81

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14588
_diffrn_reflns_av_unetI/netI     0.3764
_diffrn_reflns_av_R_equivalents  0.3564
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.079
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3447
_reflns_number_gt                881
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0990P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3447
_refine_ls_number_parameters     275
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.3628
_refine_ls_R_factor_gt           0.1167
_refine_ls_wR_factor_ref         0.3037
_refine_ls_wR_factor_gt          0.2072
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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
F1 F 0.1945(16) 0.6218(3) 0.2951(4) 0.135(3) Uani 1 1 d . . . . .
F2 F 0.5590(16) 0.6482(3) 0.2787(5) 0.113(3) Uani 1 1 d . . . . .
F3 F 0.2553(13) 0.6970(3) 0.2500(4) 0.100(2) Uani 1 1 d . . . . .
O1 O -0.1032(15) 0.5805(3) 0.4974(5) 0.095(3) Uani 1 1 d . . . . .
O2 O 0.7235(13) 0.7493(3) 0.3253(4) 0.072(2) Uani 1 1 d . . . . .
N2 N 0.7783(14) 0.7781(3) 0.4862(5) 0.052(2) Uani 1 1 d . . . . .
N5 N 0.2253(16) 0.6486(3) 0.4774(6) 0.064(3) Uani 1 1 d D . . . .
H5 H 0.100(12) 0.632(3) 0.450(7) 0.077 Uiso 1 1 d D U . . .
C1 C 0.6649(17) 0.7693(4) 0.5831(6) 0.051(3) Uani 1 1 d . . . . .
H1A H 0.793169 0.767502 0.639447 0.062 Uiso 1 1 calc R U . . .
H1B H 0.549645 0.795548 0.595119 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6832(18) 0.7468(4) 0.4133(7) 0.059(3) Uani 1 1 d . . . . .
C3A C 0.524(2) 0.7112(4) 0.4566(7) 0.056(3) Uani 1 1 d . . . . .
C4 C 0.3699(18) 0.6755(4) 0.4183(7) 0.052(3) Uani 1 1 d . . . . .
C6 C 0.2008(19) 0.6594(4) 0.5758(7) 0.056(3) Uani 1 1 d . . . . .
C7A C 0.535(3) 0.7221(5) 0.5676(7) 0.109(5) Uani 1 1 d . . . . .
H7AA H 0.667614 0.699264 0.593819 0.130 Uiso 1 1 calc R U . . .
C7 C 0.343(2) 0.7044(5) 0.6140(7) 0.092(4) Uani 1 1 d . . . . .
H7A H 0.223206 0.731095 0.615233 0.111 Uiso 1 1 calc R U . . .
H7B H 0.406760 0.697833 0.682943 0.111 Uiso 1 1 calc R U . . .
C8 C 0.342(3) 0.6609(5) 0.3111(8) 0.079(4) Uani 1 1 d . . . . .
C9 C 0.0585(18) 0.6315(4) 0.6295(7) 0.056(3) Uani 1 1 d . . . . .
H9A H 0.060371 0.638420 0.697298 0.068 Uiso 1 1 calc R U . . .
C10 C -0.094(2) 0.5922(4) 0.5890(8) 0.070(3) Uani 1 1 d . . . . .
C11 C 0.9462(18) 0.8166(4) 0.4773(6) 0.046(3) Uani 1 1 d . . . . .
C12 C 0.9540(19) 0.8561(4) 0.5422(7) 0.063(3) Uani 1 1 d . . . . .
H12A H 0.841060 0.857392 0.589415 0.075 Uiso 1 1 calc R U . . .
C13 C 1.124(2) 0.8936(4) 0.5391(7) 0.070(3) Uani 1 1 d . . . . .
H13A H 1.127827 0.919963 0.583457 0.084 Uiso 1 1 calc R U . . .
C14 C 1.2914(19) 0.8909(4) 0.4674(8) 0.069(3) Uani 1 1 d . . . . .
H14A H 1.409833 0.915583 0.463633 0.083 Uiso 1 1 calc R U . . .
C15 C 1.280(2) 0.8520(5) 0.4031(7) 0.067(3) Uani 1 1 d . . . . .
H15A H 1.393024 0.850572 0.356081 0.080 Uiso 1 1 calc R U . . .
C16 C 1.1101(19) 0.8153(4) 0.4048(7) 0.057(3) Uani 1 1 d . . . . .
H16A H 1.103407 0.789744 0.358346 0.069 Uiso 1 1 calc R U . . .
C21 C -0.2442(19) 0.5631(4) 0.6530(8) 0.059(3) Uani 1 1 d . . . . .
C22 C -0.447(2) 0.5378(4) 0.6099(8) 0.078(4) Uani 1 1 d . . . . .
H22A H -0.493006 0.541365 0.541636 0.094 Uiso 1 1 calc R U . . .
C23 C -0.590(2) 0.5064(5) 0.6647(11) 0.095(4) Uani 1 1 d . . . . .
H23A H -0.718390 0.487421 0.632842 0.114 Uiso 1 1 calc R U . . .
C24 C -0.533(2) 0.5048(5) 0.7676(9) 0.070(3) Uani 1 1 d . . . . .
C25 C -0.341(2) 0.5315(4) 0.8106(8) 0.070(3) Uani 1 1 d . . . . .
H25A H -0.303051 0.529630 0.879579 0.084 Uiso 1 1 calc R U . . .
C26 C -0.1962(18) 0.5619(4) 0.7562(7) 0.061(3) Uani 1 1 d . . . . .
H26A H -0.069447 0.581037 0.788904 0.074 Uiso 1 1 calc R U . . .
C27 C -0.6931(19) 0.4723(4) 0.8267(9) 0.094(4) Uani 1 1 d . . . . .
H27A H -0.848854 0.465848 0.787339 0.141 Uiso 1 1 calc R U . . .
H27B H -0.722874 0.488862 0.887291 0.141 Uiso 1 1 calc R U . . .
H27C H -0.608742 0.441615 0.842761 0.141 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
F1 C8 1.328(13) . ?
F2 C8 1.343(13) . ?
F3 C8 1.327(13) . ?
O1 C10 1.268(10) . ?
O2 C3 1.230(10) . ?
N2 C3 1.353(11) . ?
N2 C11 1.396(10) . ?
N2 C1 1.521(10) . ?
N5 C6 1.377(11) . ?
N5 C4 1.384(11) . ?
N5 H5 0.86(2) . ?
C1 C7A 1.462(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C3A 1.458(13) . ?
C3A C4 1.341(12) . ?
C3A C7A 1.517(12) . ?
C4 C8 1.488(13) . ?
C6 C9 1.346(12) . ?
C6 C7 1.500(13) . ?
C7A C7 1.360(13) . ?
C7A H7AA 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.418(12) . ?
C9 H9A 0.9300 . ?
C10 C21 1.475(13) . ?
C11 C12 1.378(12) . ?
C11 C16 1.390(11) . ?
C12 C13 1.373(12) . ?
C12 H12A 0.9300 . ?
C13 C14 1.397(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.359(13) . ?
C14 H14A 0.9300 . ?
C15 C16 1.355(13) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C21 C22 1.368(13) . ?
C21 C26 1.385(12) . ?
C22 C23 1.409(14) . ?
C22 H22A 0.9300 . ?
C23 C24 1.385(15) . ?
C23 H23A 0.9300 . ?
C24 C25 1.338(13) . ?
C24 C27 1.522(13) . ?
C25 C26 1.399(12) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C11 127.1(8) . . ?
C3 N2 C1 111.5(8) . . ?
C11 N2 C1 121.2(7) . . ?
C6 N5 C4 124.2(9) . . ?
C6 N5 H5 112(7) . . ?
C4 N5 H5 119(7) . . ?
C7A C1 N2 104.3(7) . . ?
C7A C1 H1A 110.9 . . ?
N2 C1 H1A 110.9 . . ?
C7A C1 H1B 110.9 . . ?
N2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
O2 C3 N2 124.8(10) . . ?
O2 C3 C3A 126.7(10) . . ?
N2 C3 C3A 108.5(8) . . ?
C4 C3A C3 133.8(9) . . ?
C4 C3A C7A 118.3(9) . . ?
C3 C3A C7A 107.7(9) . . ?
C3A C4 N5 121.6(9) . . ?
C3A C4 C8 123.8(10) . . ?
N5 C4 C8 114.6(9) . . ?
C9 C6 N5 121.3(9) . . ?
C9 C6 C7 124.9(9) . . ?
N5 C6 C7 113.7(9) . . ?
C7 C7A C1 128.4(10) . . ?
C7 C7A C3A 115.8(10) . . ?
C1 C7A C3A 106.0(8) . . ?
C7 C7A H7AA 100.4 . . ?
C1 C7A H7AA 100.4 . . ?
C3A C7A H7AA 100.4 . . ?
C7A C7 C6 121.1(10) . . ?
C7A C7 H7A 107.1 . . ?
C6 C7 H7A 107.1 . . ?
C7A C7 H7B 107.1 . . ?
C6 C7 H7B 107.1 . . ?
H7A C7 H7B 106.8 . . ?
F3 C8 F1 108.8(11) . . ?
F3 C8 F2 104.4(10) . . ?
F1 C8 F2 105.9(11) . . ?
F3 C8 C4 113.4(11) . . ?
F1 C8 C4 111.3(10) . . ?
F2 C8 C4 112.6(11) . . ?
C6 C9 C10 123.9(9) . . ?
C6 C9 H9A 118.1 . . ?
C10 C9 H9A 118.1 . . ?
O1 C10 C9 121.3(10) . . ?
O1 C10 C21 118.1(9) . . ?
C9 C10 C21 120.6(9) . . ?
C12 C11 C16 119.2(9) . . ?
C12 C11 N2 119.9(9) . . ?
C16 C11 N2 120.9(9) . . ?
C13 C12 C11 121.7(10) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C12 C13 C14 118.2(10) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
C15 C14 C13 119.4(10) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C16 C15 C14 122.8(10) . . ?
C16 C15 H15A 118.6 . . ?
C14 C15 H15A 118.6 . . ?
C15 C16 C11 118.6(10) . . ?
C15 C16 H16A 120.7 . . ?
C11 C16 H16A 120.7 . . ?
C22 C21 C26 117.7(10) . . ?
C22 C21 C10 119.2(10) . . ?
C26 C21 C10 123.0(10) . . ?
C21 C22 C23 122.8(11) . . ?
C21 C22 H22A 118.6 . . ?
C23 C22 H22A 118.6 . . ?
C24 C23 C22 117.8(11) . . ?
C24 C23 H23A 121.1 . . ?
C22 C23 H23A 121.1 . . ?
C25 C24 C23 119.5(11) . . ?
C25 C24 C27 123.0(11) . . ?
C23 C24 C27 117.6(12) . . ?
C24 C25 C26 122.8(10) . . ?
C24 C25 H25A 118.6 . . ?
C26 C25 H25A 118.6 . . ?
C21 C26 C25 119.1(10) . . ?
C21 C26 H26A 120.5 . . ?
C25 C26 H26A 120.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 C7A 12.9(12) . . . . ?
C11 N2 C1 C7A -171.1(9) . . . . ?
C11 N2 C3 O2 -3.5(16) . . . . ?
C1 N2 C3 O2 172.3(10) . . . . ?
C11 N2 C3 C3A 177.7(8) . . . . ?
C1 N2 C3 C3A -6.6(11) . . . . ?
O2 C3 C3A C4 -5(2) . . . . ?
N2 C3 C3A C4 173.4(11) . . . . ?
O2 C3 C3A C7A 179.0(11) . . . . ?
N2 C3 C3A C7A -2.2(12) . . . . ?
C3 C3A C4 N5 -175.6(10) . . . . ?
C7A C3A C4 N5 -0.5(17) . . . . ?
C3 C3A C4 C8 5(2) . . . . ?
C7A C3A C4 C8 -179.6(12) . . . . ?
C6 N5 C4 C3A 8.5(16) . . . . ?
C6 N5 C4 C8 -172.3(11) . . . . ?
C4 N5 C6 C9 -179.5(10) . . . . ?
C4 N5 C6 C7 1.2(15) . . . . ?
N2 C1 C7A C7 -156.9(13) . . . . ?
N2 C1 C7A C3A -13.2(13) . . . . ?
C4 C3A C7A C7 -17.3(19) . . . . ?
C3 C3A C7A C7 159.1(12) . . . . ?
C4 C3A C7A C1 -166.2(10) . . . . ?
C3 C3A C7A C1 10.1(14) . . . . ?
C1 C7A C7 C6 168.4(11) . . . . ?
C3A C7A C7 C6 27.7(19) . . . . ?
C9 C6 C7 C7A 160.5(12) . . . . ?
N5 C6 C7 C7A -20.2(17) . . . . ?
C3A C4 C8 F3 -62.5(17) . . . . ?
N5 C4 C8 F3 118.2(11) . . . . ?
C3A C4 C8 F1 174.4(11) . . . . ?
N5 C4 C8 F1 -4.8(16) . . . . ?
C3A C4 C8 F2 55.7(17) . . . . ?
N5 C4 C8 F2 -123.5(11) . . . . ?
N5 C6 C9 C10 -6.0(16) . . . . ?
C7 C6 C9 C10 173.2(11) . . . . ?
C6 C9 C10 O1 0.7(17) . . . . ?
C6 C9 C10 C21 179.8(10) . . . . ?
C3 N2 C11 C12 155.0(9) . . . . ?
C1 N2 C11 C12 -20.4(13) . . . . ?
C3 N2 C11 C16 -26.4(14) . . . . ?
C1 N2 C11 C16 158.3(8) . . . . ?
C16 C11 C12 C13 -1.8(14) . . . . ?
N2 C11 C12 C13 176.9(9) . . . . ?
C11 C12 C13 C14 0.2(15) . . . . ?
C12 C13 C14 C15 0.5(15) . . . . ?
C13 C14 C15 C16 0.5(16) . . . . ?
C14 C15 C16 C11 -2.1(16) . . . . ?
C12 C11 C16 C15 2.8(14) . . . . ?
N2 C11 C16 C15 -175.9(9) . . . . ?
O1 C10 C21 C22 -22.9(16) . . . . ?
C9 C10 C21 C22 158.0(11) . . . . ?
O1 C10 C21 C26 160.0(11) . . . . ?
C9 C10 C21 C26 -19.1(16) . . . . ?
C26 C21 C22 C23 -7.4(17) . . . . ?
C10 C21 C22 C23 175.4(11) . . . . ?
C21 C22 C23 C24 5.5(19) . . . . ?
C22 C23 C24 C25 -2.2(18) . . . . ?
C22 C23 C24 C27 177.9(11) . . . . ?
C23 C24 C25 C26 1.0(18) . . . . ?
C27 C24 C25 C26 -179.0(10) . . . . ?
C22 C21 C26 C25 5.9(16) . . . . ?
C10 C21 C26 C25 -177.0(10) . . . . ?
C24 C25 C26 C21 -2.9(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O1 0.86(2) 1.93(7) 2.594(11) 133(9) . yes
C1 H1A O2 0.97 2.61 3.278(10) 126.2 4_576 yes
C16 H16A O2 0.93 2.33 2.866(13) 116.5 . yes

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.066


# start Validation Reply Form
_vrf_RINTA01_P67                 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Small crystal.
;
_vrf_PLAT020_P67                 
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.356 Report
RESPONSE: Small crystal.
;
_vrf_PLAT026_P67                 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 26% Check
RESPONSE: Small crystal.
;
_vrf_PLAT340_P67                 
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01539 Ang.
RESPONSE: Small crystal.
;
_vrf_PLAT910_P67                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 14 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_13a_LT
_database_code_depnum_ccdc_archive 'CCDC 2350935'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   23.2034(17)
_cell_length_b                   6.2396(5)
_cell_length_c                   22.4373(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3248.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2596
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      20.20

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22620
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.129
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5945
_reflns_number_gt                3967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.991

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1198P)²+7.4342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5945
_refine_ls_number_parameters     451
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.1018
_refine_ls_wR_factor_ref         0.2764
_refine_ls_wR_factor_gt          0.2458
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.4572(4) 1.1529(15) 0.4426(4) 0.089(3) Uani 1 1 d D . . . .
O2 O 0.6976(3) 1.1382(13) 0.6133(4) 0.068(2) Uani 1 1 d D . . . .
N2 N 0.6732(5) 0.8287(18) 0.6450(4) 0.071(3) Uani 1 1 d . . . . .
N5 N 0.5363(6) 1.0592(15) 0.5092(4) 0.079(4) Uani 1 1 d . . . . .
H5A H 0.520320 1.156363 0.486009 0.094 Uiso 1 1 calc R U . . .
C1 C 0.6282(6) 0.667(2) 0.6298(6) 0.077(4) Uani 1 1 d . U . . .
H1A H 0.611226 0.602683 0.666196 0.092 Uiso 1 1 calc R U . . .
H1B H 0.644060 0.551450 0.604405 0.092 Uiso 1 1 calc R U . . .
C3 C 0.6636(6) 0.992(2) 0.6144(7) 0.078(4) Uani 1 1 d D . . . .
C3A C 0.6079(5) 0.989(3) 0.5770(6) 0.067(3) Uani 1 1 d . . . . .
C4 C 0.5915(5) 1.0968(19) 0.5403(6) 0.054(3) Uani 1 1 d . U . . .
H4A H 0.614261 1.216640 0.528892 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5105(5) 0.8543(17) 0.5193(6) 0.059(3) Uani 1 1 d . . . . .
C7 C 0.5465(4) 0.7029(16) 0.5521(4) 0.045(2) Uani 1 1 d . . . . .
H7A H 0.521310 0.597923 0.572446 0.054 Uiso 1 1 calc R U . . .
H7B H 0.570740 0.623020 0.523312 0.054 Uiso 1 1 calc R U . . .
C7A C 0.5835(7) 0.802(2) 0.5958(7) 0.093(5) Uani 1 1 d . . . . .
H7AA H 0.556099 0.849440 0.627588 0.112 Uiso 1 1 calc R U . . .
C11 C 0.4613(4) 0.791(3) 0.4871(5) 0.071(4) Uani 1 1 d . . . . .
H11A H 0.445173 0.651390 0.489602 0.086 Uiso 1 1 calc R U . . .
C12 C 0.4367(4) 0.9641(15) 0.4487(4) 0.044(2) Uani 1 1 d D . . . .
C13 C 0.3845(4) 0.9093(15) 0.4146(4) 0.038(2) Uani 1 1 d . . . . .
C14 C 0.3560(4) 0.7085(18) 0.4191(5) 0.053(3) Uani 1 1 d . . . . .
H14A H 0.369981 0.600747 0.445329 0.063 Uiso 1 1 calc R U . . .
C15 C 0.3067(4) 0.672(2) 0.3841(5) 0.058(3) Uani 1 1 d . . . . .
H15A H 0.287307 0.538225 0.386085 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2862(5) 0.834(2) 0.3464(5) 0.068(3) Uani 1 1 d . . . . .
H16A H 0.252416 0.809524 0.323493 0.081 Uiso 1 1 calc R U . . .
C17 C 0.3132(6) 1.021(2) 0.3420(6) 0.070(3) Uani 1 1 d . . . . .
H17A H 0.299136 1.127772 0.315703 0.084 Uiso 1 1 calc R U . . .
C18 C 0.3630(5) 1.0596(17) 0.3769(5) 0.054(3) Uani 1 1 d . . . . .
H18A H 0.381939 1.194215 0.373720 0.064 Uiso 1 1 calc R U . . .
C21 C 0.7230(4) 0.7832(16) 0.6816(3) 0.041(2) Uani 1 1 d . . . . .
C22 C 0.7611(6) 0.9320(18) 0.7000(5) 0.064(3) Uani 1 1 d . . . . .
H22A H 0.755324 1.077847 0.689344 0.077 Uiso 1 1 calc R U . . .
C23 C 0.8088(5) 0.8758(18) 0.7344(5) 0.058(3) Uani 1 1 d . . . . .
H23A H 0.835765 0.982429 0.746132 0.070 Uiso 1 1 calc R U . . .
C24 C 0.8171(5) 0.663(2) 0.7515(5) 0.055(3) Uani 1 1 d . . . . .
H24A H 0.849070 0.622540 0.775382 0.067 Uiso 1 1 calc R U . . .
C25 C 0.7780(5) 0.5156(18) 0.7329(5) 0.060(3) Uani 1 1 d . . . . .
H25A H 0.783896 0.369241 0.742785 0.072 Uiso 1 1 calc R U . . .
C26 C 0.7297(5) 0.5711(17) 0.7000(5) 0.051(3) Uani 1 1 d . . . . .
H26A H 0.701577 0.466335 0.690082 0.061 Uiso 1 1 calc R U . . .
O1B O 0.1708(3) 0.5170(12) 0.4804(3) 0.0561(18) Uani 1 1 d D . . . .
O2B O 0.4003(4) 0.7579(13) 0.6647(4) 0.068(2) Uani 1 1 d D . . . .
N2B N 0.4341(3) 0.4308(13) 0.6465(4) 0.046(2) Uani 1 1 d . . . . .
N5B N 0.2669(4) 0.5172(14) 0.5428(4) 0.060(3) Uani 1 1 d . . . . .
H5BA H 0.235806 0.588950 0.532417 0.072 Uiso 1 1 calc R U . . .
C1B C 0.4173(5) 0.251(2) 0.6094(5) 0.065(3) Uani 1 1 d . . . . .
H1BA H 0.404114 0.129503 0.634357 0.078 Uiso 1 1 calc R U . . .
H1BB H 0.450188 0.202254 0.584769 0.078 Uiso 1 1 calc R U . . .
C3B C 0.3976(5) 0.5898(15) 0.6381(5) 0.056(3) Uani 1 1 d D . . . .
C3BA C 0.3515(6) 0.5279(17) 0.5925(5) 0.057(3) Uani 1 1 d . . . . .
C4B C 0.3077(6) 0.6087(18) 0.5818(5) 0.057(3) Uani 1 1 d . . . . .
H4BA H 0.299011 0.742128 0.600110 0.068 Uiso 1 1 calc R U . . .
C6B C 0.2764(6) 0.315(2) 0.5214(5) 0.077(4) Uani 1 1 d . . . . .
C7B C 0.3256(4) 0.1859(15) 0.5492(5) 0.046(2) Uani 1 1 d . . . . .
H7BA H 0.310668 0.098286 0.582593 0.055 Uiso 1 1 calc R U . . .
H7BB H 0.342226 0.087918 0.519061 0.055 Uiso 1 1 calc R U . . .
C7BA C 0.3694(6) 0.329(2) 0.5707(8) 0.086(5) Uani 1 1 d . . . . .
H7BC H 0.390087 0.369096 0.533205 0.104 Uiso 1 1 calc R U . . .
C11B C 0.2362(5) 0.207(2) 0.4826(5) 0.065(3) Uani 1 1 d . . . . .
H11B H 0.242358 0.063463 0.469613 0.077 Uiso 1 1 calc R U . . .
C12B C 0.1853(5) 0.3308(16) 0.4644(4) 0.062(3) Uani 1 1 d D . . . .
C13B C 0.1470(4) 0.2043(15) 0.4217(4) 0.040(2) Uani 1 1 d . . . . .
C14B C 0.1514(4) -0.0054(16) 0.4026(4) 0.042(2) Uani 1 1 d . . . . .
H14B H 0.182327 -0.091034 0.416776 0.050 Uiso 1 1 calc R U . . .
C15B C 0.1123(5) -0.0943(16) 0.3636(5) 0.051(3) Uani 1 1 d . . . . .
H15B H 0.116832 -0.237944 0.350381 0.061 Uiso 1 1 calc R U . . .
C16B C 0.0658(5) 0.030(2) 0.3436(5) 0.054(3) Uani 1 1 d . . . . .
H16B H 0.038212 -0.030295 0.317172 0.065 Uiso 1 1 calc R U . . .
C17B C 0.0603(5) 0.232(2) 0.3616(5) 0.067(3) Uani 1 1 d . . . . .
H17B H 0.028592 0.314789 0.347838 0.080 Uiso 1 1 calc R U . . .
C18B C 0.0998(5) 0.3235(18) 0.4000(4) 0.054(3) Uani 1 1 d . . . . .
H18B H 0.095129 0.468537 0.412016 0.065 Uiso 1 1 calc R U . . .
C21B C 0.4810(4) 0.4161(14) 0.6889(4) 0.035(2) Uani 1 1 d . . . . .
C22B C 0.4968(5) 0.5816(17) 0.7270(5) 0.058(3) Uani 1 1 d . . . . .
H22B H 0.475675 0.712098 0.727363 0.069 Uiso 1 1 calc R U . . .
C23B C 0.5432(6) 0.5539(19) 0.7641(6) 0.072(4) Uani 1 1 d . . . . .
H23B H 0.554013 0.669054 0.789436 0.086 Uiso 1 1 calc R U . . .
C24B C 0.5745(4) 0.3686(18) 0.7664(5) 0.055(3) Uani 1 1 d . . . . .
H24B H 0.606982 0.356292 0.792016 0.066 Uiso 1 1 calc R U . . .
C25B C 0.5576(5) 0.1981(19) 0.7302(5) 0.056(3) Uani 1 1 d . . . . .
H25B H 0.576730 0.063796 0.732381 0.067 Uiso 1 1 calc R U . . .
C26B C 0.5118(5) 0.2289(18) 0.6907(5) 0.056(3) Uani 1 1 d . . . . .
H26B H 0.501728 0.116313 0.664125 0.067 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 C12 1.278(7) . ?
O2 C3 1.208(7) . ?
N2 C3 1.247(16) . ?
N2 C21 1.446(14) . ?
N2 C1 1.492(18) . ?
N5 C6 1.429(15) . ?
N5 C4 1.479(17) . ?
N5 H5A 0.8800 . ?
C1 C7A 1.541(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C3A 1.542(19) . ?
C3A C4 1.129(17) . ?
C3A C7A 1.36(2) . ?
C4 H4A 0.9500 . ?
C6 C11 1.408(15) . ?
C6 C7 1.460(15) . ?
C7 C7A 1.443(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7A H7AA 1.0000 . ?
C11 C12 1.494(18) . ?
C11 H11A 0.9500 . ?
C12 C13 1.472(13) . ?
C13 C18 1.359(14) . ?
C13 C14 1.420(14) . ?
C14 C15 1.406(14) . ?
C14 H14A 0.9500 . ?
C15 C16 1.401(16) . ?
C15 H15A 0.9500 . ?
C16 C17 1.325(18) . ?
C16 H16A 0.9500 . ?
C17 C18 1.417(17) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C21 C22 1.346(15) . ?
C21 C26 1.394(14) . ?
C22 C23 1.395(17) . ?
C22 H22A 0.9500 . ?
C23 C24 1.395(16) . ?
C23 H23A 0.9500 . ?
C24 C25 1.358(16) . ?
C24 H24A 0.9500 . ?
C25 C26 1.385(15) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
O1B C12B 1.261(7) . ?
O2B C3B 1.209(7) . ?
N2B C3B 1.318(12) . ?
N2B C21B 1.447(12) . ?
N2B C1B 1.452(14) . ?
N5B C6B 1.368(17) . ?
N5B C4B 1.411(16) . ?
N5B H5BA 0.8800 . ?
C1B C7BA 1.492(17) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C3B C3BA 1.529(17) . ?
C3BA C4B 1.160(16) . ?
C3BA C7BA 1.398(18) . ?
C4B H4BA 0.9500 . ?
C6B C11B 1.443(16) . ?
C6B C7B 1.529(18) . ?
C7B C7BA 1.435(16) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7BA H7BC 1.0000 . ?
C11B C12B 1.472(16) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.526(14) . ?
C13B C14B 1.381(14) . ?
C13B C18B 1.411(15) . ?
C14B C15B 1.376(14) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.403(16) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.330(17) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.383(16) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C21B C26B 1.370(14) . ?
C21B C22B 1.390(14) . ?
C22B C23B 1.372(18) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.367(16) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.396(15) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.397(15) . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?

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
C3 N2 C21 128.0(12) . . ?
C3 N2 C1 107.5(11) . . ?
C21 N2 C1 123.8(10) . . ?
C6 N5 C4 115.4(9) . . ?
C6 N5 H5A 122.3 . . ?
C4 N5 H5A 122.3 . . ?
N2 C1 C7A 102.3(11) . . ?
N2 C1 H1A 111.3 . . ?
C7A C1 H1A 111.3 . . ?
N2 C1 H1B 111.3 . . ?
C7A C1 H1B 111.3 . . ?
H1A C1 H1B 109.2 . . ?
O2 C3 N2 120.8(14) . . ?
O2 C3 C3A 123.0(13) . . ?
N2 C3 C3A 116.2(11) . . ?
C4 C3A C7A 126.6(13) . . ?
C4 C3A C3 132.3(14) . . ?
C7A C3A C3 100.9(13) . . ?
C3A C4 N5 122.8(11) . . ?
C3A C4 H4A 118.6 . . ?
N5 C4 H4A 118.6 . . ?
C11 C6 N5 120.5(12) . . ?
C11 C6 C7 122.8(11) . . ?
N5 C6 C7 114.8(9) . . ?
C7A C7 C6 113.8(9) . . ?
C7A C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C7A C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C3A C7A C7 113.9(13) . . ?
C3A C7A C1 110.1(13) . . ?
C7 C7A C1 120.1(10) . . ?
C3A C7A H7AA 103.5 . . ?
C7 C7A H7AA 103.5 . . ?
C1 C7A H7AA 103.5 . . ?
C6 C11 C12 113.8(12) . . ?
C6 C11 H11A 123.1 . . ?
C12 C11 H11A 123.1 . . ?
O1 C12 C13 117.7(10) . . ?
O1 C12 C11 125.9(10) . . ?
C13 C12 C11 116.5(9) . . ?
C18 C13 C14 118.8(9) . . ?
C18 C13 C12 117.7(9) . . ?
C14 C13 C12 123.4(9) . . ?
C15 C14 C13 118.8(10) . . ?
C15 C14 H14A 120.6 . . ?
C13 C14 H14A 120.6 . . ?
C16 C15 C14 119.8(11) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C17 C16 C15 121.2(11) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C16 C17 C18 119.7(11) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C13 C18 C17 121.6(10) . . ?
C13 C18 H18A 119.2 . . ?
C17 C18 H18A 119.2 . . ?
C22 C21 C26 119.4(9) . . ?
C22 C21 N2 124.2(10) . . ?
C26 C21 N2 116.3(9) . . ?
C21 C22 C23 121.1(10) . . ?
C21 C22 H22A 119.4 . . ?
C23 C22 H22A 119.4 . . ?
C24 C23 C22 120.0(10) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C25 C24 C23 117.9(11) . . ?
C25 C24 H24A 121.0 . . ?
C23 C24 H24A 121.0 . . ?
C24 C25 C26 122.3(11) . . ?
C24 C25 H25A 118.8 . . ?
C26 C25 H25A 118.8 . . ?
C25 C26 C21 119.0(10) . . ?
C25 C26 H26A 120.5 . . ?
C21 C26 H26A 120.5 . . ?
C3B N2B C21B 128.7(9) . . ?
C3B N2B C1B 109.0(9) . . ?
C21B N2B C1B 122.0(8) . . ?
C6B N5B C4B 118.8(10) . . ?
C6B N5B H5BA 120.6 . . ?
C4B N5B H5BA 120.6 . . ?
N2B C1B C7BA 106.4(11) . . ?
N2B C1B H1BA 110.5 . . ?
C7BA C1B H1BA 110.5 . . ?
N2B C1B H1BB 110.5 . . ?
C7BA C1B H1BB 110.5 . . ?
H1BA C1B H1BB 108.6 . . ?
O2B C3B N2B 123.3(11) . . ?
O2B C3B C3BA 125.8(10) . . ?
N2B C3B C3BA 110.8(8) . . ?
C4B C3BA C7BA 125.0(13) . . ?
C4B C3BA C3B 129.9(11) . . ?
C7BA C3BA C3B 104.6(10) . . ?
C3BA C4B N5B 122.8(11) . . ?
C3BA C4B H4BA 118.6 . . ?
N5B C4B H4BA 118.6 . . ?
N5B C6B C11B 122.6(14) . . ?
N5B C6B C7B 117.6(10) . . ?
C11B C6B C7B 118.8(12) . . ?
C7BA C7B C6B 109.8(9) . . ?
C7BA C7B H7BA 109.7 . . ?
C6B C7B H7BA 109.7 . . ?
C7BA C7B H7BB 109.7 . . ?
C6B C7B H7BB 109.7 . . ?
H7BA C7B H7BB 108.2 . . ?
C3BA C7BA C7B 117.4(12) . . ?
C3BA C7BA C1B 107.9(12) . . ?
C7B C7BA C1B 121.3(11) . . ?
C3BA C7BA H7BC 102.4 . . ?
C7B C7BA H7BC 102.4 . . ?
C1B C7BA H7BC 102.3 . . ?
C6B C11B C12B 116.1(12) . . ?
C6B C11B H11B 122.0 . . ?
C12B C11B H11B 122.0 . . ?
O1B C12B C11B 128.3(11) . . ?
O1B C12B C13B 120.1(10) . . ?
C11B C12B C13B 111.6(9) . . ?
C14B C13B C18B 116.7(9) . . ?
C14B C13B C12B 130.0(9) . . ?
C18B C13B C12B 113.3(9) . . ?
C15B C14B C13B 122.1(9) . . ?
C15B C14B H14B 119.0 . . ?
C13B C14B H14B 119.0 . . ?
C14B C15B C16B 119.2(10) . . ?
C14B C15B H15B 120.4 . . ?
C16B C15B H15B 120.4 . . ?
C17B C16B C15B 120.1(11) . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C16B C17B C18B 121.1(12) . . ?
C16B C17B H17B 119.4 . . ?
C18B C17B H17B 119.4 . . ?
C17B C18B C13B 120.8(11) . . ?
C17B C18B H18B 119.6 . . ?
C13B C18B H18B 119.6 . . ?
C26B C21B C22B 118.6(9) . . ?
C26B C21B N2B 117.7(8) . . ?
C22B C21B N2B 123.7(8) . . ?
C23B C22B C21B 119.1(10) . . ?
C23B C22B H22B 120.4 . . ?
C21B C22B H22B 120.4 . . ?
C22B C23B C24B 123.2(11) . . ?
C22B C23B H23B 118.4 . . ?
C24B C23B H23B 118.4 . . ?
C23B C24B C25B 118.2(10) . . ?
C23B C24B H24B 120.9 . . ?
C25B C24B H24B 120.9 . . ?
C24B C25B C26B 118.7(10) . . ?
C24B C25B H25B 120.7 . . ?
C26B C25B H25B 120.7 . . ?
C21B C26B C25B 122.2(10) . . ?
C21B C26B H26B 118.9 . . ?
C25B C26B H26B 118.9 . . ?

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
C3 N2 C1 C7A -13.8(14) . . . . ?
C21 N2 C1 C7A 175.1(10) . . . . ?
C21 N2 C3 O2 -1(2) . . . . ?
C1 N2 C3 O2 -171.8(12) . . . . ?
C21 N2 C3 C3A 176.6(9) . . . . ?
C1 N2 C3 C3A 6.0(15) . . . . ?
O2 C3 C3A C4 9(2) . . . . ?
N2 C3 C3A C4 -168.6(15) . . . . ?
O2 C3 C3A C7A -176.7(13) . . . . ?
N2 C3 C3A C7A 5.7(15) . . . . ?
C7A C3A C4 N5 5(2) . . . . ?
C3 C3A C4 N5 178.4(11) . . . . ?
C6 N5 C4 C3A -12.7(16) . . . . ?
C4 N5 C6 C11 -173.0(10) . . . . ?
C4 N5 C6 C7 -8.1(14) . . . . ?
C11 C6 C7 C7A -162.3(13) . . . . ?
N5 C6 C7 C7A 33.2(16) . . . . ?
C4 C3A C7A C7 22(2) . . . . ?
C3 C3A C7A C7 -152.5(11) . . . . ?
C4 C3A C7A C1 160.4(13) . . . . ?
C3 C3A C7A C1 -14.4(14) . . . . ?
C6 C7 C7A C3A -40.6(17) . . . . ?
C6 C7 C7A C1 -174.2(13) . . . . ?
N2 C1 C7A C3A 18.2(14) . . . . ?
N2 C1 C7A C7 153.3(14) . . . . ?
N5 C6 C11 C12 -6.5(15) . . . . ?
C7 C6 C11 C12 -170.2(10) . . . . ?
C6 C11 C12 O1 1.7(14) . . . . ?
C6 C11 C12 C13 -179.0(9) . . . . ?
O1 C12 C13 C18 2.9(12) . . . . ?
C11 C12 C13 C18 -176.5(9) . . . . ?
O1 C12 C13 C14 -177.3(9) . . . . ?
C11 C12 C13 C14 3.3(12) . . . . ?
C18 C13 C14 C15 0.3(14) . . . . ?
C12 C13 C14 C15 -179.5(9) . . . . ?
C13 C14 C15 C16 -0.9(16) . . . . ?
C14 C15 C16 C17 1.3(18) . . . . ?
C15 C16 C17 C18 -1(2) . . . . ?
C14 C13 C18 C17 -0.1(15) . . . . ?
C12 C13 C18 C17 179.7(10) . . . . ?
C16 C17 C18 C13 0.5(18) . . . . ?
C3 N2 C21 C22 17.0(16) . . . . ?
C1 N2 C21 C22 -173.8(10) . . . . ?
C3 N2 C21 C26 -165.3(12) . . . . ?
C1 N2 C21 C26 3.9(13) . . . . ?
C26 C21 C22 C23 3.5(16) . . . . ?
N2 C21 C22 C23 -178.8(10) . . . . ?
C21 C22 C23 C24 -1.5(17) . . . . ?
C22 C23 C24 C25 1.0(16) . . . . ?
C23 C24 C25 C26 -2.6(17) . . . . ?
C24 C25 C26 C21 4.7(17) . . . . ?
C22 C21 C26 C25 -5.0(14) . . . . ?
N2 C21 C26 C25 177.1(9) . . . . ?
C3B N2B C1B C7BA 7.0(12) . . . . ?
C21B N2B C1B C7BA -178.1(10) . . . . ?
C21B N2B C3B O2B 3.2(17) . . . . ?
C1B N2B C3B O2B 177.7(10) . . . . ?
C21B N2B C3B C3BA -174.7(8) . . . . ?
C1B N2B C3B C3BA -0.3(11) . . . . ?
O2B C3B C3BA C4B -13(2) . . . . ?
N2B C3B C3BA C4B 164.8(13) . . . . ?
O2B C3B C3BA C7BA 175.2(12) . . . . ?
N2B C3B C3BA C7BA -6.9(13) . . . . ?
C7BA C3BA C4B N5B -2(2) . . . . ?
C3B C3BA C4B N5B -172.6(10) . . . . ?
C6B N5B C4B C3BA 7.0(17) . . . . ?
C4B N5B C6B C11B 178.3(10) . . . . ?
C4B N5B C6B C7B 10.0(15) . . . . ?
N5B C6B C7B C7BA -28.5(16) . . . . ?
C11B C6B C7B C7BA 162.7(12) . . . . ?
C4B C3BA C7BA C7B -20(2) . . . . ?
C3B C3BA C7BA C7B 152.3(12) . . . . ?
C4B C3BA C7BA C1B -161.4(13) . . . . ?
C3B C3BA C7BA C1B 10.9(15) . . . . ?
C6B C7B C7BA C3BA 32.9(18) . . . . ?
C6B C7B C7BA C1B 168.9(13) . . . . ?
N2B C1B C7BA C3BA -11.4(15) . . . . ?
N2B C1B C7BA C7B -151.0(13) . . . . ?
N5B C6B C11B C12B 3.1(15) . . . . ?
C7B C6B C11B C12B 171.3(10) . . . . ?
C6B C11B C12B O1B -3.3(15) . . . . ?
C6B C11B C12B C13B 177.8(9) . . . . ?
O1B C12B C13B C14B -173.6(9) . . . . ?
C11B C12B C13B C14B 5.4(13) . . . . ?
O1B C12B C13B C18B 5.1(12) . . . . ?
C11B C12B C13B C18B -175.9(8) . . . . ?
C18B C13B C14B C15B 1.0(13) . . . . ?
C12B C13B C14B C15B 179.7(9) . . . . ?
C13B C14B C15B C16B -1.5(14) . . . . ?
C14B C15B C16B C17B 1.0(15) . . . . ?
C15B C16B C17B C18B 0.0(17) . . . . ?
C16B C17B C18B C13B -0.5(16) . . . . ?
C14B C13B C18B C17B 0.0(13) . . . . ?
C12B C13B C18B C17B -178.9(9) . . . . ?
C3B N2B C21B C26B 177.6(10) . . . . ?
C1B N2B C21B C26B 3.7(12) . . . . ?
C3B N2B C21B C22B -3.3(15) . . . . ?
C1B N2B C21B C22B -177.1(9) . . . . ?
C26B C21B C22B C23B 1.4(16) . . . . ?
N2B C21B C22B C23B -177.8(10) . . . . ?
C21B C22B C23B C24B -1(2) . . . . ?
C22B C23B C24B C25B -2(2) . . . . ?
C23B C24B C25B C26B 4.0(18) . . . . ?
C22B C21B C26B C25B 1.3(16) . . . . ?
N2B C21B C26B C25B -179.5(10) . . . . ?
C24B C25B C26B C21B -4.0(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A O1 0.88 1.76 2.437(15) 132.0 . yes
C4 H4A O1B 0.95 2.38 3.317(13) 168.0 3_575 yes
C22 H22A O2 0.95 2.20 2.758(15) 116.4 . yes
N5B H5BA O1B 0.88 1.96 2.632(13) 132.2 . yes
C1B H1BA O2B 0.99 2.42 3.340(15) 154.7 1_545 yes
C4B H4BA O2 0.95 2.49 3.087(16) 121.1 3_475 yes
C22B H22B O2B 0.95 2.26 2.859(15) 120.1 . yes

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.071


# start Validation Reply Form
_vrf_PLAT230_13a_LT              
;
PROBLEM: Hirshfeld Test Diff for O1 --C12 . 9.4 s.u. 
RESPONSE: Small crystal.
;
_vrf_PLAT340_13a_LT              
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01643 Ang. 
RESPONSE: Small crystal.
;
_vrf_PLAT368_13a_LT              
;
PROBLEM: Short C(sp2)-C(sp2) Bond C3A - C4 . 1.13 Ang. 
RESPONSE: Small crystal.
;
_vrf_PLAT910_13a_LT              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 17 Note 
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
