# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_1n_CCPh
_database_code_depnum_ccdc_archive 'CCDC 2007763'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2021-11-19 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         'C27 H16 N3 O'
_chemical_formula_sum            'C27 H16 N3 O'
_chemical_formula_weight         398.43

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

_space_group_crystal_system      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                   18.3724(7)
_cell_length_b                   13.2094(5)
_cell_length_c                   8.0305(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.937(4)
_cell_angle_gamma                90
_cell_volume                     1930.24(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    5409
_cell_measurement_theta_min      4.1240
_cell_measurement_theta_max      76.2310

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.676
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.780
_oxdiff_exptl_absorpt_empirical_full_max 1.569
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17388
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.136
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_full        67.073
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3441
_reflns_number_gt                2334
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²+0.9664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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         3441
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1923
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_restrained_S_all      1.235
_refine_ls_shift/su_max          0.004
_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
O7 O 0.09765(11) 0.16396(13) -0.1411(3) 0.0438(5) Uani 1 1 d . . . . .
N12 N 0.16018(13) 0.33997(16) 0.0159(3) 0.0397(6) Uani 1 1 d . . . . .
C12 C 0.33534(18) 0.1272(2) 0.3809(5) 0.0501(6) Uani 1 1 d . . . . .
N3 N 0.10210(12) 0.52778(17) -0.0762(3) 0.0405(6) Uani 1 1 d . . . . .
N1 N 0.19240(13) 0.42386(16) 0.0916(3) 0.0403(6) Uani 1 1 d . . . . .
C2 C 0.16145(15) 0.5122(2) 0.0394(3) 0.0387(6) Uani 1 1 d . . . . .
C3A C 0.07020(16) 0.4417(2) -0.1521(4) 0.0397(7) Uani 1 1 d . . . . .
C008 C 0.09936(15) 0.34573(19) -0.1068(4) 0.0388(7) Uani 1 1 d . . . . .
C6A C 0.06832(16) 0.2585(2) -0.1834(4) 0.0407(7) Uani 1 1 d . . . . .
C21 C 0.19933(16) 0.6014(2) 0.1223(3) 0.0405(7) Uani 1 1 d . . . . .
C11A C 0.18950(16) 0.2451(2) 0.0650(4) 0.0403(7) Uani 1 1 d . . . . .
C22 C 0.16157(16) 0.6922(2) 0.1327(4) 0.0422(7) Uani 1 1 d . . . . .
H22 H 0.112478 0.696857 0.085883 0.051 Uiso 1 1 calc R U . . .
C11 C 0.24865(16) 0.2349(2) 0.1919(4) 0.0432(7) Uani 1 1 d . . . . .
H11 H 0.270407 0.292070 0.245084 0.052 Uiso 1 1 calc R U . . .
C7A C 0.15769(16) 0.1588(2) -0.0159(4) 0.0417(7) Uani 1 1 d . . . . .
C4 C 0.00912(16) 0.4475(2) -0.2772(4) 0.0423(7) Uani 1 1 d . . . . .
H4 H -0.011025 0.510129 -0.310328 0.051 Uiso 1 1 calc R U . . .
C7 C 0.00780(17) 0.2639(2) -0.3047(4) 0.0435(7) Uani 1 1 d . . . . .
H7 H -0.013462 0.205520 -0.354590 0.052 Uiso 1 1 calc R U . . .
C8 C 0.18561(17) 0.0637(2) 0.0267(4) 0.0482(8) Uani 1 1 d . . . . .
H8 H 0.165186 0.006579 -0.029286 0.058 Uiso 1 1 calc R U . . .
C10 C 0.27523(16) 0.1389(2) 0.2391(4) 0.0462(7) Uani 1 1 d . . . . .
C5 C -0.02111(16) 0.3599(2) -0.3513(4) 0.0442(7) Uani 1 1 d . . . . .
H5 H -0.061653 0.364607 -0.434218 0.053 Uiso 1 1 calc R U . . .
C23 C 0.19646(18) 0.7754(2) 0.2119(4) 0.0471(7) Uani 1 1 d . . . . .
H23 H 0.170444 0.835058 0.221591 0.056 Uiso 1 1 calc R U . . .
C9 C 0.24417(17) 0.0546(2) 0.1532(4) 0.0493(8) Uani 1 1 d . . . . .
H9 H 0.263284 -0.009272 0.181588 0.059 Uiso 1 1 calc R U . . .
C26 C 0.27315(17) 0.5962(2) 0.1892(4) 0.0490(8) Uani 1 1 d . . . . .
H26 H 0.298893 0.535972 0.183885 0.059 Uiso 1 1 calc R U . . .
C24 C 0.26997(19) 0.7699(2) 0.2767(4) 0.0530(8) Uani 1 1 d . . . . .
H24 H 0.293638 0.826039 0.329003 0.064 Uiso 1 1 calc R U . . .
C25 C 0.30843(19) 0.6808(2) 0.2638(4) 0.0560(8) Uani 1 1 d . . . . .
H25 H 0.358193 0.677694 0.305336 0.067 Uiso 1 1 calc R U . . .
C14 C 0.43936(19) 0.1050(3) 0.6314(4) 0.0573(9) Uani 1 1 d . . . . .
C13 C 0.37858(18) 0.1232(2) 0.4860(4) 0.0501(6) Uani 1 1 d . . . . .
C15 C 0.4672(2) 0.0091(3) 0.6754(5) 0.0630(9) Uani 1 1 d . . . . .
H15 H 0.445369 -0.047880 0.621875 0.076 Uiso 1 1 calc R U . . .
C19 C 0.4716(2) 0.1884(3) 0.7198(5) 0.0727(11) Uani 1 1 d . . . . .
H19 H 0.452773 0.252903 0.695642 0.087 Uiso 1 1 calc R U . . .
C16 C 0.5272(2) -0.0016(3) 0.7981(5) 0.0734(11) Uani 1 1 d . . . . .
H16 H 0.545839 -0.065811 0.825481 0.088 Uiso 1 1 calc R U . . .
C17 C 0.5596(2) 0.0808(4) 0.8796(5) 0.0800(12) Uani 1 1 d . . . . .
H17 H 0.600850 0.072951 0.959827 0.096 Uiso 1 1 calc R U . . .
C18 C 0.5310(2) 0.1755(4) 0.8424(6) 0.0829(12) Uani 1 1 d . . . . .
H18 H 0.551919 0.231493 0.900740 0.099 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
O7 C6A 1.384(3) . ?
O7 C7A 1.388(4) . ?
N12 N1 1.360(3) . ?
N12 C008 1.386(4) . ?
N12 C11A 1.399(3) . ?
C12 C13 1.077(4) . ?
C12 C10 1.481(5) . ?
N3 C2 1.346(4) . ?
N3 C3A 1.382(3) . ?
N1 C2 1.340(3) . ?
C2 C21 1.479(4) . ?
C3A C4 1.401(4) . ?
C3A C008 1.404(4) . ?
C008 C6A 1.391(4) . ?
C6A C7 1.375(4) . ?
C21 C26 1.390(4) . ?
C21 C22 1.394(4) . ?
C11A C11 1.390(4) . ?
C11A C7A 1.399(4) . ?
C22 C23 1.383(4) . ?
C22 H22 0.9300 . ?
C11 C10 1.393(4) . ?
C11 H11 0.9300 . ?
C7A C8 1.382(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C7 C5 1.406(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9300 . ?
C10 C9 1.391(4) . ?
C5 H5 0.9300 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9300 . ?
C9 H9 0.9300 . ?
C26 C25 1.385(4) . ?
C26 H26 0.9300 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C14 C15 1.393(5) . ?
C14 C19 1.397(5) . ?
C14 C13 1.519(5) . ?
C15 C16 1.381(5) . ?
C15 H15 0.9300 . ?
C19 C18 1.375(6) . ?
C19 H19 0.9300 . ?
C16 C17 1.363(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(6) . ?
C17 H17 0.9300 . ?
C18 H18 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
C6A O7 C7A 117.8(2) . . ?
N1 N12 C008 122.1(2) . . ?
N1 N12 C11A 118.5(2) . . ?
C008 N12 C11A 119.4(2) . . ?
C13 C12 C10 176.7(4) . . ?
C2 N3 C3A 115.6(2) . . ?
C2 N1 N12 115.5(2) . . ?
N1 C2 N3 128.1(3) . . ?
N1 C2 C21 113.6(2) . . ?
N3 C2 C21 118.3(2) . . ?
N3 C3A C4 121.3(2) . . ?
N3 C3A C008 120.3(3) . . ?
C4 C3A C008 118.3(3) . . ?
N12 C008 C6A 120.7(2) . . ?
N12 C008 C3A 118.4(2) . . ?
C6A C008 C3A 121.0(3) . . ?
C7 C6A O7 118.1(2) . . ?
C7 C6A C008 120.8(3) . . ?
O7 C6A C008 121.1(3) . . ?
C26 C21 C22 119.1(3) . . ?
C26 C21 C2 120.6(3) . . ?
C22 C21 C2 120.3(3) . . ?
C11 C11A C7A 119.7(3) . . ?
C11 C11A N12 121.6(3) . . ?
C7A C11A N12 118.6(3) . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C11A C11 C10 119.8(3) . . ?
C11A C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C8 C7A O7 117.0(3) . . ?
C8 C7A C11A 120.6(3) . . ?
O7 C7A C11A 122.4(2) . . ?
C5 C4 C3A 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3A C4 H4 120.1 . . ?
C6A C7 C5 118.3(3) . . ?
C6A C7 H7 120.8 . . ?
C5 C7 H7 120.8 . . ?
C9 C8 C7A 119.1(3) . . ?
C9 C8 H8 120.5 . . ?
C7A C8 H8 120.5 . . ?
C9 C10 C11 119.3(3) . . ?
C9 C10 C12 120.6(3) . . ?
C11 C10 C12 120.1(3) . . ?
C4 C5 C7 121.7(3) . . ?
C4 C5 H5 119.1 . . ?
C7 C5 H5 119.1 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C8 C9 C10 121.4(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C25 C26 C21 120.1(3) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C15 C14 C19 118.2(4) . . ?
C15 C14 C13 123.0(3) . . ?
C19 C14 C13 118.7(3) . . ?
C12 C13 C14 173.7(4) . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C18 C19 C14 120.3(4) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.6(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 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
C008 N12 N1 C2 -0.1(3) . . . . ?
C11A N12 N1 C2 -179.7(2) . . . . ?
N12 N1 C2 N3 1.1(4) . . . . ?
N12 N1 C2 C21 -178.7(2) . . . . ?
C3A N3 C2 N1 -1.3(4) . . . . ?
C3A N3 C2 C21 178.5(2) . . . . ?
C2 N3 C3A C4 -178.5(2) . . . . ?
C2 N3 C3A C008 0.5(4) . . . . ?
N1 N12 C008 C6A 179.1(2) . . . . ?
C11A N12 C008 C6A -1.2(4) . . . . ?
N1 N12 C008 C3A -0.6(4) . . . . ?
C11A N12 C008 C3A 179.0(2) . . . . ?
N3 C3A C008 N12 0.4(4) . . . . ?
C4 C3A C008 N12 179.4(2) . . . . ?
N3 C3A C008 C6A -179.3(2) . . . . ?
C4 C3A C008 C6A -0.3(4) . . . . ?
C7A O7 C6A C7 -178.6(2) . . . . ?
C7A O7 C6A C008 2.0(4) . . . . ?
N12 C008 C6A C7 179.7(2) . . . . ?
C3A C008 C6A C7 -0.5(4) . . . . ?
N12 C008 C6A O7 -0.8(4) . . . . ?
C3A C008 C6A O7 178.9(2) . . . . ?
N1 C2 C21 C26 24.8(4) . . . . ?
N3 C2 C21 C26 -155.0(3) . . . . ?
N1 C2 C21 C22 -155.9(2) . . . . ?
N3 C2 C21 C22 24.3(4) . . . . ?
N1 N12 C11A C11 2.2(4) . . . . ?
C008 N12 C11A C11 -177.5(2) . . . . ?
N1 N12 C11A C7A -178.3(2) . . . . ?
C008 N12 C11A C7A 2.0(4) . . . . ?
C26 C21 C22 C23 -1.5(4) . . . . ?
C2 C21 C22 C23 179.2(3) . . . . ?
C7A C11A C11 C10 -0.8(4) . . . . ?
N12 C11A C11 C10 178.7(2) . . . . ?
C6A O7 C7A C8 179.1(2) . . . . ?
C6A O7 C7A C11A -1.1(4) . . . . ?
C11 C11A C7A C8 -1.5(4) . . . . ?
N12 C11A C7A C8 178.9(2) . . . . ?
C11 C11A C7A O7 178.7(2) . . . . ?
N12 C11A C7A O7 -0.9(4) . . . . ?
N3 C3A C4 C5 179.6(2) . . . . ?
C008 C3A C4 C5 0.6(4) . . . . ?
O7 C6A C7 C5 -178.4(2) . . . . ?
C008 C6A C7 C5 1.1(4) . . . . ?
O7 C7A C8 C9 -178.5(2) . . . . ?
C11A C7A C8 C9 1.7(4) . . . . ?
C11A C11 C10 C9 2.9(4) . . . . ?
C11A C11 C10 C12 -176.4(3) . . . . ?
C3A C4 C5 C7 0.0(4) . . . . ?
C6A C7 C5 C4 -0.8(4) . . . . ?
C21 C22 C23 C24 2.1(4) . . . . ?
C7A C8 C9 C10 0.4(4) . . . . ?
C11 C10 C9 C8 -2.7(4) . . . . ?
C12 C10 C9 C8 176.6(3) . . . . ?
C22 C21 C26 C25 -0.5(5) . . . . ?
C2 C21 C26 C25 178.8(3) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C23 C24 C25 C26 -1.4(5) . . . . ?
C21 C26 C25 C24 2.0(5) . . . . ?
C19 C14 C15 C16 -2.9(5) . . . . ?
C13 C14 C15 C16 173.7(3) . . . . ?
C15 C14 C19 C18 2.4(6) . . . . ?
C13 C14 C19 C18 -174.3(3) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C18 1.8(6) . . . . ?
C16 C17 C18 C19 -2.3(7) . . . . ?
C14 C19 C18 C17 0.2(6) . . . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_1l_Ph
_database_code_depnum_ccdc_archive 'CCDC 2007764'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H16 N3 O'
_chemical_formula_sum            'C25 H16 N3 O'
_chemical_formula_weight         374.41

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

_space_group_crystal_system      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                   21.5515(6)
_cell_length_b                   5.02080(10)
_cell_length_c                   18.0754(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.476(3)
_cell_angle_gamma                90
_cell_volume                     1793.97(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    13186
_cell_measurement_theta_min      4.4670
_cell_measurement_theta_max      77.4080

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.687
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.788
_oxdiff_exptl_absorpt_empirical_full_max 1.286
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32411
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.474
_diffrn_reflns_theta_max         70.053
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3393
_reflns_number_gt                2842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0897P)²+1.4293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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         3393
_refine_ls_number_parameters     287
_refine_ls_number_restraints     151
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1753
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.047
_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
O7 O 0.11433(8) 0.4652(3) 0.24249(9) 0.0375(4) Uani 1 1 d . . . . .
N12 N 0.17895(9) 0.1300(3) 0.17044(10) 0.0319(4) Uani 1 1 d . . . . .
N1 N 0.21202(9) -0.0230(3) 0.13566(10) 0.0319(4) Uani 1 1 d . . . . .
N3 N 0.10902(9) -0.2697(3) 0.06724(10) 0.0335(4) Uani 1 1 d . . . . .
C3AA C 0.11148(11) 0.0977(4) 0.15429(12) 0.0315(5) Uani 1 1 d . . . . .
C2 C 0.17364(11) -0.2131(4) 0.08593(12) 0.0307(5) Uani 1 1 d . . . . .
C21 C 0.21107(11) -0.3753(4) 0.04817(12) 0.0314(5) Uani 1 1 d . . . . .
C11A C 0.21670(11) 0.3250(4) 0.22582(12) 0.0320(5) Uani 1 1 d . . . . .
C7A C 0.18205(11) 0.4897(4) 0.25963(12) 0.0341(5) Uani 1 1 d . . . . .
C3A C 0.07599(11) -0.1093(4) 0.10174(12) 0.0328(5) Uani 1 1 d . . . . .
C6A C 0.07906(12) 0.2621(4) 0.19055(13) 0.0345(5) Uani 1 1 d . . . . .
C11 C 0.28530(12) 0.3516(4) 0.24814(12) 0.0340(5) Uani 1 1 d . . . . .
H11 H 0.307468 0.239136 0.225743 0.041 Uiso 1 1 calc R U . . .
C10 C 0.32228(12) 0.5450(4) 0.30399(12) 0.0361(5) Uani 1 1 d . . . . .
C24 C 0.27864(12) -0.6917(4) -0.02239(13) 0.0377(5) Uani 1 1 d . . . . .
H24 H 0.301401 -0.799272 -0.045261 0.045 Uiso 1 1 calc R U . . .
C26 C 0.27973(11) -0.3438(4) 0.06934(13) 0.0366(5) Uani 1 1 d . . . . .
H26 H 0.303465 -0.216923 0.107663 0.044 Uiso 1 1 calc R U . . .
C9 C 0.28644(13) 0.7133(4) 0.33530(13) 0.0386(5) Uani 1 1 d . . . . .
H9 H 0.309729 0.845556 0.371825 0.046 Uiso 1 1 calc R U . . .
C8 C 0.21788(13) 0.6872(4) 0.31333(13) 0.0376(5) Uani 1 1 d . . . . .
H8 H 0.195418 0.802579 0.334559 0.045 Uiso 1 1 calc R U . . .
C23 C 0.21042(12) -0.7224(4) -0.04431(13) 0.0387(5) Uani 1 1 d . . . . .
H23 H 0.186864 -0.849100 -0.082786 0.046 Uiso 1 1 calc R U . . .
C22 C 0.17629(12) -0.5662(4) -0.00959(13) 0.0362(5) Uani 1 1 d . . . . .
H22 H 0.130001 -0.588595 -0.024840 0.043 Uiso 1 1 calc R U . . .
C6 C 0.01203(12) 0.2255(5) 0.17455(14) 0.0392(5) Uani 1 1 d . . . . .
H6 H -0.009724 0.335413 0.198118 0.047 Uiso 1 1 calc R U . . .
C12 C 0.39664(8) 0.5604(4) 0.33035(12) 0.0410(5) Uani 1 1 d DG U . . .
C17B C 0.43142(11) 0.7956(3) 0.36103(19) 0.0455(13) Uani 0.476(4) 1 d G U P A 2
H17B H 0.407858 0.947638 0.363954 0.055 Uiso 0.476(4) 1 calc R U P A 2
C16B C 0.50142(11) 0.8035(4) 0.3873(2) 0.0533(15) Uani 0.476(4) 1 d G U P A 2
H16B H 0.524694 0.960789 0.407854 0.064 Uiso 0.476(4) 1 calc R U P A 2
C15 C 0.53664(9) 0.5762(5) 0.38295(18) 0.0667(8) Uani 1 1 d G U . A .
H15 H 0.582292 0.608535 0.396055 0.080 Uiso 1 1 calc R U . B 1
C14B C 0.50185(11) 0.3411(4) 0.3523(2) 0.0566(16) Uani 0.476(4) 1 d G U P A 2
H14B H 0.525416 0.189007 0.349347 0.068 Uiso 0.476(4) 1 calc R U P A 2
C13B C 0.43185(11) 0.3332(4) 0.3260(2) 0.0469(14) Uani 0.476(4) 1 d G U P A 2
H13B H 0.408580 0.175850 0.305446 0.056 Uiso 0.476(4) 1 calc R U P A 2
C17A C 0.4385(3) 0.6236(10) 0.4169(3) 0.0551(14) Uani 0.524(4) 1 d D U P A 1
H17A H 0.417519 0.663352 0.451640 0.066 Uiso 0.524(4) 1 calc R U P A 1
C16A C 0.5088(3) 0.6231(11) 0.4456(3) 0.0654(16) Uani 0.524(4) 1 d . U P A 1
H16A H 0.536353 0.649976 0.499666 0.078 Uiso 0.524(4) 1 calc R U P A 1
C14A C 0.5020(3) 0.4981(11) 0.3162(3) 0.0549(13) Uani 0.524(4) 1 d . U P A 1
H14A H 0.522799 0.432623 0.283678 0.066 Uiso 0.524(4) 1 calc R U P A 1
C13A C 0.4328(2) 0.5030(10) 0.2870(3) 0.0465(12) Uani 0.524(4) 1 d . U P A 1
H13A H 0.409040 0.463214 0.232651 0.056 Uiso 0.524(4) 1 calc R U P A 1
C4 C 0.00783(11) -0.1440(4) 0.08624(13) 0.0374(5) Uani 1 1 d . . . . .
H4 H -0.016751 -0.278355 0.051512 0.045 Uiso 1 1 calc R U . . .
C25 C 0.31362(12) -0.4998(5) 0.03396(14) 0.0392(5) Uani 1 1 d . . . . .
H25 H 0.359709 -0.475610 0.048037 0.047 Uiso 1 1 calc R U . . .
C5 C -0.02343(12) 0.0206(5) 0.12232(14) 0.0405(5) Uani 1 1 d . . . . .
H5 H -0.068924 -0.005302 0.111651 0.049 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
O7 C7A 1.371(3) . ?
O7 C6A 1.389(3) . ?
N12 N1 1.360(2) . ?
N12 C3AA 1.374(3) . ?
N12 C11A 1.405(3) . ?
N1 C2 1.346(3) . ?
N3 C2 1.326(3) . ?
N3 C3A 1.378(3) . ?
C3AA C6A 1.402(3) . ?
C3AA C3A 1.410(3) . ?
C2 C21 1.489(3) . ?
C21 C26 1.382(3) . ?
C21 C22 1.395(3) . ?
C11A C11 1.375(3) . ?
C11A C7A 1.406(3) . ?
C7A C8 1.388(3) . ?
C3A C4 1.392(3) . ?
C6A C6 1.368(3) . ?
C11 C10 1.399(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.407(3) . ?
C10 C12 1.481(3) . ?
C24 C23 1.370(3) . ?
C24 C25 1.386(3) . ?
C24 H24 0.9300 . ?
C26 C25 1.389(3) . ?
C26 H26 0.9300 . ?
C9 C8 1.375(3) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C23 C22 1.385(3) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C6 C5 1.399(3) . ?
C6 H6 0.9300 . ?
C12 C13A 1.339(5) . ?
C12 C17B 1.3900 . ?
C12 C13B 1.3900 . ?
C12 C17A 1.496(5) . ?
C17B C16B 1.3900 . ?
C17B H17B 0.9300 . ?
C16B C15 1.3900 . ?
C16B H16B 0.9300 . ?
C15 C14A 1.203(6) . ?
C15 C14B 1.3900 . ?
C15 C16A 1.496(7) . ?
C15 H15 0.9300 . ?
C14B C13B 1.3900 . ?
C14B H14B 0.9300 . ?
C13B H13B 0.9300 . ?
C17A C16A 1.391(8) . ?
C17A H17A 0.9300 . ?
C16A H16A 0.9300 . ?
C14A C13A 1.370(7) . ?
C14A H14A 0.9300 . ?
C13A H13A 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C25 H25 0.9300 . ?
C5 H5 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
C7A O7 C6A 117.70(16) . . ?
N1 N12 C3AA 122.69(17) . . ?
N1 N12 C11A 117.49(17) . . ?
C3AA N12 C11A 119.82(17) . . ?
C2 N1 N12 114.43(18) . . ?
C2 N3 C3A 116.04(18) . . ?
N12 C3AA C6A 120.90(19) . . ?
N12 C3AA C3A 118.32(18) . . ?
C6A C3AA C3A 120.8(2) . . ?
N3 C2 N1 128.73(19) . . ?
N3 C2 C21 118.14(18) . . ?
N1 C2 C21 113.13(18) . . ?
C26 C21 C22 118.85(19) . . ?
C26 C21 C2 121.75(19) . . ?
C22 C21 C2 119.4(2) . . ?
C11 C11A N12 121.77(19) . . ?
C11 C11A C7A 120.68(19) . . ?
N12 C11A C7A 117.5(2) . . ?
O7 C7A C8 117.88(19) . . ?
O7 C7A C11A 123.41(19) . . ?
C8 C7A C11A 118.7(2) . . ?
N3 C3A C4 122.0(2) . . ?
N3 C3A C3AA 119.75(19) . . ?
C4 C3A C3AA 118.26(19) . . ?
C6 C6A O7 119.27(19) . . ?
C6 C6A C3AA 120.2(2) . . ?
O7 C6A C3AA 120.5(2) . . ?
C11A C11 C10 121.1(2) . . ?
C11A C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C10 C9 117.5(2) . . ?
C11 C10 C12 120.1(2) . . ?
C9 C10 C12 122.44(19) . . ?
C23 C24 C25 119.8(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C21 C26 C25 120.6(2) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C8 C9 C10 121.7(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C8 C7A 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7A C8 H8 119.8 . . ?
C24 C23 C22 120.5(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C6A C6 C5 119.2(2) . . ?
C6A C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C17B C12 C13B 120.0 . . ?
C13A C12 C10 127.4(3) . . ?
C17B C12 C10 121.02(15) . . ?
C13B C12 C10 118.96(15) . . ?
C13A C12 C17A 114.1(3) . . ?
C10 C12 C17A 118.2(3) . . ?
C12 C17B C16B 120.0 . . ?
C12 C17B H17B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C15 C16B C17B 120.0 . . ?
C15 C16B H16B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C16B C15 C14B 120.0 . . ?
C14A C15 C16A 122.3(4) . . ?
C14A C15 H15 118.9 . . ?
C16A C15 H15 118.9 . . ?
C13B C14B C15 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C15 C14B H14B 120.0 . . ?
C14B C13B C12 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C12 C13B H13B 120.0 . . ?
C16A C17A C12 120.2(5) . . ?
C16A C17A H17A 119.9 . . ?
C12 C17A H17A 119.9 . . ?
C17A C16A C15 115.1(4) . . ?
C17A C16A H16A 122.5 . . ?
C15 C16A H16A 122.5 . . ?
C15 C14A C13A 121.8(5) . . ?
C15 C14A H14A 119.1 . . ?
C13A C14A H14A 119.1 . . ?
C12 C13A C14A 125.2(4) . . ?
C12 C13A H13A 117.4 . . ?
C14A C13A H13A 117.4 . . ?
C5 C4 C3A 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3A C4 H4 119.9 . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_1k_I
_database_code_depnum_ccdc_archive 'CCDC 2007765'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2021-11-19 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         'C19 H11 I N3 O'
_chemical_formula_sum            'C19 H11 I N3 O'
_chemical_formula_weight         424.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 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+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   28.8753(2)
_cell_length_b                   13.04560(10)
_cell_length_c                   8.02440(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3022.76(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    22513
_cell_measurement_theta_min      3.7110
_cell_measurement_theta_max      78.4630

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    16.737
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.808
_oxdiff_exptl_absorpt_empirical_full_max 1.721
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34519
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.718
_diffrn_reflns_theta_max         78.670
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3242
_reflns_number_gt                3014
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+3.2602P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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         3242
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.003
_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
I1 I 0.26784(2) 0.09827(2) 0.78907(2) 0.01973(7) Uani 1 1 d . . . . .
O7 O 0.43734(6) 0.15376(12) 0.3158(2) 0.0185(3) Uani 1 1 d . . . . .
C7A C 0.39915(8) 0.14648(17) 0.4187(3) 0.0167(4) Uani 1 1 d . . . . .
N1 N 0.37570(7) 0.41302(14) 0.5243(2) 0.0159(4) Uani 1 1 d . . . . .
N12 N 0.39583(6) 0.32983(14) 0.4534(2) 0.0149(4) Uani 1 1 d . . . . .
N3 N 0.43283(7) 0.52101(14) 0.3911(2) 0.0179(4) Uani 1 1 d . . . . .
C11 C 0.33917(8) 0.21983(17) 0.5940(3) 0.0159(4) Uani 1 1 d . . . . .
H11 H 0.324509 0.276168 0.641510 0.019 Uiso 1 1 calc R U . . .
C10 C 0.32349(8) 0.12100(18) 0.6249(3) 0.0172(4) Uani 1 1 d . . . . .
C11A C 0.37776(7) 0.23270(16) 0.4891(3) 0.0144(4) Uani 1 1 d . . . . .
C3AA C 0.43459(8) 0.33735(17) 0.3519(3) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.39587(8) 0.50305(17) 0.4877(3) 0.0159(4) Uani 1 1 d . . . . .
C3A C 0.45274(8) 0.43558(18) 0.3206(3) 0.0164(4) Uani 1 1 d . . . . .
C22 C 0.39836(8) 0.68330(18) 0.5929(3) 0.0190(5) Uani 1 1 d . . . . .
H22 H 0.428621 0.688387 0.554039 0.023 Uiso 1 1 calc R U . . .
C25 C 0.30782(9) 0.6697(2) 0.7073(3) 0.0245(5) Uani 1 1 d . . . . .
H25 H 0.277426 0.665192 0.744980 0.029 Uiso 1 1 calc R U . . .
C9 C 0.34438(8) 0.03576(17) 0.5534(3) 0.0199(5) Uani 1 1 d . . . . .
H9 H 0.333029 -0.029659 0.574680 0.024 Uiso 1 1 calc R U . . .
C21 C 0.37366(8) 0.59245(16) 0.5700(3) 0.0167(4) Uani 1 1 d . . . . .
C26 C 0.32812(8) 0.58637(17) 0.6278(3) 0.0207(5) Uani 1 1 d . . . . .
H26 H 0.311297 0.526268 0.613040 0.025 Uiso 1 1 calc R U . . .
C6A C 0.45513(8) 0.24998(18) 0.2840(3) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.38236(8) 0.04933(17) 0.4500(3) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.396567 -0.007272 0.401496 0.024 Uiso 1 1 calc R U . . .
C4 C 0.49133(8) 0.44300(19) 0.2145(3) 0.0198(5) Uani 1 1 d . . . . .
H4 H 0.503716 0.506929 0.189193 0.024 Uiso 1 1 calc R U . . .
C24 C 0.33269(9) 0.7594(2) 0.7307(3) 0.0238(5) Uani 1 1 d . . . . .
H24 H 0.319144 0.814902 0.784554 0.029 Uiso 1 1 calc R U . . .
C23 C 0.37813(8) 0.76587(18) 0.6731(3) 0.0215(5) Uani 1 1 d . . . . .
H23 H 0.394925 0.825954 0.688534 0.026 Uiso 1 1 calc R U . . .
C6 C 0.49315(8) 0.25777(19) 0.1832(3) 0.0189(4) Uani 1 1 d . . . . .
H6 H 0.506950 0.199389 0.138931 0.023 Uiso 1 1 calc R U . . .
C5 C 0.51094(8) 0.35529(19) 0.1477(3) 0.0200(5) Uani 1 1 d . . . . .
H5 H 0.536477 0.361234 0.077722 0.024 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
I1 C10 2.099(2) . ?
O7 C6A 1.380(3) . ?
O7 C7A 1.381(3) . ?
C7A C8 1.380(3) . ?
C7A C11A 1.402(3) . ?
N1 C2 1.343(3) . ?
N1 N12 1.356(3) . ?
N12 C3AA 1.387(3) . ?
N12 C11A 1.400(3) . ?
N3 C2 1.340(3) . ?
N3 C3A 1.376(3) . ?
C11 C10 1.389(3) . ?
C11 C11A 1.407(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.389(3) . ?
C3AA C6A 1.396(3) . ?
C3AA C3A 1.407(3) . ?
C2 C21 1.486(3) . ?
C3A C4 1.405(3) . ?
C22 C23 1.384(3) . ?
C22 C21 1.395(3) . ?
C22 H22 0.9300 . ?
C25 C24 1.386(4) . ?
C25 C26 1.390(3) . ?
C25 H25 0.9300 . ?
C9 C8 1.387(3) . ?
C9 H9 0.9300 . ?
C21 C26 1.397(3) . ?
C26 H26 0.9300 . ?
C6A C6 1.368(3) . ?
C8 H8 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C24 C23 1.394(3) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C6 C5 1.401(3) . ?
C6 H6 0.9300 . ?
C5 H5 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
C6A O7 C7A 118.05(17) . . ?
C8 C7A O7 116.9(2) . . ?
C8 C7A C11A 120.6(2) . . ?
O7 C7A C11A 122.5(2) . . ?
C2 N1 N12 114.95(19) . . ?
N1 N12 C3AA 122.37(18) . . ?
N1 N12 C11A 118.60(18) . . ?
C3AA N12 C11A 118.99(18) . . ?
C2 N3 C3A 115.43(19) . . ?
C10 C11 C11A 118.4(2) . . ?
C10 C11 H11 120.8 . . ?
C11A C11 H11 120.8 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 I1 119.53(17) . . ?
C9 C10 I1 118.59(17) . . ?
N12 C11A C7A 118.65(19) . . ?
N12 C11A C11 121.72(19) . . ?
C7A C11A C11 119.63(19) . . ?
N12 C3AA C6A 120.9(2) . . ?
N12 C3AA C3A 118.0(2) . . ?
C6A C3AA C3A 121.0(2) . . ?
N3 C2 N1 128.7(2) . . ?
N3 C2 C21 117.64(19) . . ?
N1 C2 C21 113.69(19) . . ?
N3 C3A C4 121.6(2) . . ?
N3 C3A C3AA 120.6(2) . . ?
C4 C3A C3AA 117.8(2) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C22 C21 C26 119.1(2) . . ?
C22 C21 C2 120.3(2) . . ?
C26 C21 C2 120.6(2) . . ?
C25 C26 C21 120.4(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C6 C6A O7 118.4(2) . . ?
C6 C6A C3AA 120.8(2) . . ?
O7 C6A C3AA 120.83(19) . . ?
C7A C8 C9 120.3(2) . . ?
C7A C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C5 C4 C3A 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C3A C4 H4 119.9 . . ?
C25 C24 C23 119.6(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C6A C6 C5 118.8(2) . . ?
C6A C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A O7 C7A C8 -179.29(19) . . . . ?
C6A O7 C7A C11A 0.9(3) . . . . ?
C2 N1 N12 C3AA 0.6(3) . . . . ?
C2 N1 N12 C11A 178.19(19) . . . . ?
C11A C11 C10 C9 -1.0(3) . . . . ?
C11A C11 C10 I1 177.33(16) . . . . ?
N1 N12 C11A C7A -178.64(19) . . . . ?
C3AA N12 C11A C7A -1.0(3) . . . . ?
N1 N12 C11A C11 0.9(3) . . . . ?
C3AA N12 C11A C11 178.6(2) . . . . ?
C8 C7A C11A N12 -179.7(2) . . . . ?
O7 C7A C11A N12 0.1(3) . . . . ?
C8 C7A C11A C11 0.7(3) . . . . ?
O7 C7A C11A C11 -179.5(2) . . . . ?
C10 C11 C11A N12 -179.4(2) . . . . ?
C10 C11 C11A C7A 0.2(3) . . . . ?
N1 N12 C3AA C6A 178.5(2) . . . . ?
C11A N12 C3AA C6A 0.9(3) . . . . ?
N1 N12 C3AA C3A -1.1(3) . . . . ?
C11A N12 C3AA C3A -178.7(2) . . . . ?
C3A N3 C2 N1 -0.1(3) . . . . ?
C3A N3 C2 C21 178.7(2) . . . . ?
N12 N1 C2 N3 0.0(3) . . . . ?
N12 N1 C2 C21 -178.79(18) . . . . ?
C2 N3 C3A C4 179.1(2) . . . . ?
C2 N3 C3A C3AA -0.4(3) . . . . ?
N12 C3AA C3A N3 1.0(3) . . . . ?
C6A C3AA C3A N3 -178.6(2) . . . . ?
N12 C3AA C3A C4 -178.5(2) . . . . ?
C6A C3AA C3A C4 1.9(3) . . . . ?
C11 C10 C9 C8 0.9(4) . . . . ?
I1 C10 C9 C8 -177.43(17) . . . . ?
C23 C22 C21 C26 0.5(4) . . . . ?
C23 C22 C21 C2 -178.5(2) . . . . ?
N3 C2 C21 C22 -21.1(3) . . . . ?
N1 C2 C21 C22 157.9(2) . . . . ?
N3 C2 C21 C26 159.9(2) . . . . ?
N1 C2 C21 C26 -21.1(3) . . . . ?
C24 C25 C26 C21 -0.3(4) . . . . ?
C22 C21 C26 C25 -0.1(4) . . . . ?
C2 C21 C26 C25 178.9(2) . . . . ?
C7A O7 C6A C6 179.5(2) . . . . ?
C7A O7 C6A C3AA -1.0(3) . . . . ?
N12 C3AA C6A C6 179.6(2) . . . . ?
C3A C3AA C6A C6 -0.9(3) . . . . ?
N12 C3AA C6A O7 0.1(3) . . . . ?
C3A C3AA C6A O7 179.7(2) . . . . ?
O7 C7A C8 C9 179.4(2) . . . . ?
C11A C7A C8 C9 -0.8(3) . . . . ?
C10 C9 C8 C7A 0.0(3) . . . . ?
N3 C3A C4 C5 179.0(2) . . . . ?
C3AA C3A C4 C5 -1.5(3) . . . . ?
C26 C25 C24 C23 0.4(4) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C25 C24 C23 C22 0.0(4) . . . . ?
O7 C6A C6 C5 178.8(2) . . . . ?
C3AA C6A C6 C5 -0.6(3) . . . . ?
C3A C4 C5 C6 0.0(4) . . . . ?
C6A C6 C5 C4 1.1(4) . . . . ?

_refine_diff_density_max         0.983
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.084

