# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

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

data_MKCYS3_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2216957'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto'
;Vellore Institute of Technology, Vellore
India
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-02-24 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 H19 N3 O5'
_chemical_formula_sum            'C27 H19 N3 O5'
_chemical_formula_weight         465.46

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.934(4)
_cell_length_b                   7.1249(19)
_cell_length_c                   23.124(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.776(8)
_cell_angle_gamma                90
_cell_volume                     2238.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9725
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      24.75

_exptl_crystal_description       block
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             964
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_T_max  0.7452
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50858
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.792
_diffrn_reflns_theta_max         25.158
_diffrn_reflns_theta_full        25.158
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3981
_reflns_number_gt                3439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_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)+(0.0501P)²+1.6694P] 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         3981
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.001
_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 0.38182(10) 0.28629(19) 0.64302(6) 0.0437(3) Uani 1 1 d . . . . .
O2 O 0.30221(11) 0.6989(2) 0.77565(6) 0.0589(4) Uani 1 1 d . . . . .
O3 O 0.57405(14) -0.0290(2) 0.62443(7) 0.0651(5) Uani 1 1 d . . . . .
O4 O 0.16123(12) 1.0993(2) 0.49099(6) 0.0582(4) Uani 1 1 d . . . . .
O5 O 0.05314(11) 0.8673(2) 0.45945(7) 0.0615(4) Uani 1 1 d . . . . .
N1 N 0.32986(11) 0.5273(2) 0.69586(6) 0.0373(4) Uani 1 1 d . . . . .
N2 N 0.59138(11) 0.2190(2) 0.68677(7) 0.0373(4) Uani 1 1 d . . . . .
N3 N 0.59799(12) 0.4093(2) 0.69980(7) 0.0407(4) Uani 1 1 d . . . . .
C1 C 0.50066(13) 0.1440(3) 0.76417(8) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.57591(13) 0.1041(3) 0.73502(8) 0.0368(4) Uani 1 1 d . . . . .
C3 C 0.63975(16) -0.0437(3) 0.75340(9) 0.0498(5) Uani 1 1 d . . . . .
H3 H 0.690558 -0.067346 0.734231 0.060 Uiso 1 1 calc R U . . .
C4 C 0.62856(18) -0.1558(3) 0.79985(10) 0.0603(6) Uani 1 1 d . . . . .
H4 H 0.671532 -0.255441 0.811762 0.072 Uiso 1 1 calc R U . . .
C5 C 0.55382(18) -0.1212(3) 0.82887(10) 0.0596(6) Uani 1 1 d . . . . .
H5 H 0.545701 -0.197942 0.859974 0.072 Uiso 1 1 calc R U . . .
C6 C 0.49122(15) 0.0285(3) 0.81128(9) 0.0480(5) Uani 1 1 d . . . . .
H6 H 0.441584 0.052832 0.831318 0.058 Uiso 1 1 calc R U . . .
C7 C 0.43491(13) 0.3078(3) 0.75064(8) 0.0362(4) Uani 1 1 d . . . . .
C8 C 0.38191(13) 0.3644(2) 0.68930(8) 0.0345(4) Uani 1 1 d . . . . .
C9 C 0.34080(14) 0.5698(3) 0.75622(8) 0.0416(4) Uani 1 1 d . . . . .
C10 C 0.40780(14) 0.4259(3) 0.78859(8) 0.0432(5) Uani 1 1 d . . . . .
H10 H 0.428142 0.418711 0.829637 0.052 Uiso 1 1 calc R U . . .
C11 C 0.60626(15) 0.5197(3) 0.65691(9) 0.0452(5) Uani 1 1 d . . . . .
H11 H 0.609336 0.647971 0.664551 0.054 Uiso 1 1 calc R U . . .
C12 C 0.61106(13) 0.4601(3) 0.59849(9) 0.0423(5) Uani 1 1 d . . . . .
C13 C 0.60193(14) 0.2690(3) 0.58555(8) 0.0415(4) Uani 1 1 d . . . . .
C14 C 0.58770(14) 0.1386(3) 0.63192(9) 0.0429(5) Uani 1 1 d . . . . .
C15 C 0.27264(13) 0.6316(3) 0.64778(8) 0.0363(4) Uani 1 1 d . . . . .
C16 C 0.20261(13) 0.5417(3) 0.60503(9) 0.0411(4) Uani 1 1 d . . . . .
H16 H 0.189889 0.414619 0.608600 0.049 Uiso 1 1 calc R U . . .
C17 C 0.15172(14) 0.6430(3) 0.55690(9) 0.0434(5) Uani 1 1 d . . . . .
H17 H 0.104580 0.583319 0.527998 0.052 Uiso 1 1 calc R U . . .
C18 C 0.17023(13) 0.8326(3) 0.55130(8) 0.0404(4) Uani 1 1 d . . . . .
C19 C 0.23896(15) 0.9215(3) 0.59537(8) 0.0441(5) Uani 1 1 d . . . . .
H19 H 0.250703 1.049238 0.592403 0.053 Uiso 1 1 calc R U . . .
C20 C 0.28987(14) 0.8218(3) 0.64343(8) 0.0417(4) Uani 1 1 d . . . . .
H20 H 0.335721 0.882127 0.672913 0.050 Uiso 1 1 calc R U . . .
C21 C 0.62288(16) 0.5863(3) 0.55378(10) 0.0534(5) Uani 1 1 d . . . . .
H21 H 0.628574 0.714301 0.561680 0.064 Uiso 1 1 calc R U . . .
C22 C 0.62596(16) 0.5203(4) 0.49868(10) 0.0597(6) Uani 1 1 d . . . . .
H22 H 0.634633 0.603500 0.469264 0.072 Uiso 1 1 calc R U . . .
C23 C 0.61626(17) 0.3308(4) 0.48657(10) 0.0633(7) Uani 1 1 d . . . . .
H23 H 0.617933 0.287868 0.448821 0.076 Uiso 1 1 calc R U . . .
C24 C 0.60423(17) 0.2049(3) 0.52901(10) 0.0567(6) Uani 1 1 d . . . . .
H24 H 0.597639 0.077516 0.520192 0.068 Uiso 1 1 calc R U . . .
C25 C 0.12036(15) 0.9323(3) 0.49592(9) 0.0473(5) Uani 1 1 d . . . . .
C26 C 0.12518(19) 1.2033(4) 0.43656(10) 0.0627(6) Uani 1 1 d . . . . .
H26A H 0.144426 1.333869 0.442680 0.075 Uiso 1 1 calc R U . . .
H26B H 0.053864 1.197902 0.426297 0.075 Uiso 1 1 calc R U . . .
C27 C 0.16501(18) 1.1253(4) 0.38657(10) 0.0649(6) Uani 1 1 d . . . . .
H27A H 0.157239 1.216171 0.355240 0.097 Uiso 1 1 calc R U . . .
H27B H 0.129792 1.012968 0.371976 0.097 Uiso 1 1 calc R U . . .
H27C H 0.233567 1.096557 0.400423 0.097 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 C8 1.206(2) . ?
O2 C9 1.201(2) . ?
O3 C14 1.216(2) . ?
O4 C25 1.335(3) . ?
O4 C26 1.451(2) . ?
O5 C25 1.205(2) . ?
N1 C8 1.395(2) . ?
N1 C9 1.403(2) . ?
N1 C15 1.426(2) . ?
N2 C14 1.382(2) . ?
N2 N3 1.388(2) . ?
N2 C2 1.438(2) . ?
N3 C11 1.291(2) . ?
C1 C2 1.396(3) . ?
C1 C6 1.395(3) . ?
C1 C7 1.474(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.381(3) . ?
C7 C10 1.329(3) . ?
C7 C8 1.502(3) . ?
C9 C10 1.475(3) . ?
C11 C12 1.432(3) . ?
C12 C13 1.394(3) . ?
C12 C21 1.407(3) . ?
C13 C24 1.392(3) . ?
C13 C14 1.465(3) . ?
C15 C16 1.383(3) . ?
C15 C20 1.384(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.388(3) . ?
C18 C25 1.495(3) . ?
C19 C20 1.376(3) . ?
C21 C22 1.368(3) . ?
C22 C23 1.380(4) . ?
C23 C24 1.367(3) . ?
C26 C27 1.496(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O4 C26 117.17(18) . . ?
C8 N1 C9 110.07(15) . . ?
C8 N1 C15 124.33(14) . . ?
C9 N1 C15 125.59(15) . . ?
C14 N2 N3 126.24(15) . . ?
C14 N2 C2 119.66(15) . . ?
N3 N2 C2 113.69(14) . . ?
C11 N3 N2 116.19(16) . . ?
C2 C1 C6 117.88(17) . . ?
C2 C1 C7 123.86(16) . . ?
C6 C1 C7 118.14(16) . . ?
C3 C2 C1 120.51(17) . . ?
C3 C2 N2 118.38(16) . . ?
C1 C2 N2 121.08(16) . . ?
C4 C3 C2 120.41(19) . . ?
C3 C4 C5 120.3(2) . . ?
C4 C5 C6 119.35(19) . . ?
C1 C6 C5 121.57(19) . . ?
C10 C7 C1 127.95(17) . . ?
C10 C7 C8 107.54(16) . . ?
C1 C7 C8 124.45(16) . . ?
O1 C8 N1 125.59(17) . . ?
O1 C8 C7 128.16(17) . . ?
N1 C8 C7 106.24(15) . . ?
O2 C9 N1 125.32(18) . . ?
O2 C9 C10 128.90(18) . . ?
N1 C9 C10 105.78(15) . . ?
C7 C10 C9 110.21(17) . . ?
N3 C11 C12 125.10(18) . . ?
C13 C12 C21 119.12(19) . . ?
C13 C12 C11 118.11(17) . . ?
C21 C12 C11 122.76(19) . . ?
C12 C13 C24 120.15(19) . . ?
C12 C13 C14 118.88(17) . . ?
C24 C13 C14 120.95(19) . . ?
O3 C14 N2 120.69(18) . . ?
O3 C14 C13 124.12(19) . . ?
N2 C14 C13 115.19(17) . . ?
C16 C15 C20 120.53(18) . . ?
C16 C15 N1 120.02(17) . . ?
C20 C15 N1 119.42(17) . . ?
C15 C16 C17 119.24(18) . . ?
C18 C17 C16 120.71(18) . . ?
C19 C18 C17 119.24(18) . . ?
C19 C18 C25 121.80(19) . . ?
C17 C18 C25 118.83(18) . . ?
C18 C19 C20 120.42(19) . . ?
C15 C20 C19 119.81(18) . . ?
C22 C21 C12 119.8(2) . . ?
C23 C22 C21 120.2(2) . . ?
C24 C23 C22 121.2(2) . . ?
C23 C24 C13 119.4(2) . . ?
O5 C25 O4 124.2(2) . . ?
O5 C25 C18 124.0(2) . . ?
O4 C25 C18 111.75(17) . . ?
O4 C26 C27 111.37(19) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_Alkane_3
_database_code_depnum_ccdc_archive 'CCDC 2232967'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto'
;Vellore Institute of Technology, Vellore
India
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-02-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         395.40

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.4045(9)
_cell_length_b                   8.8690(8)
_cell_length_c                   21.6415(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.176(2)
_cell_angle_gamma                90
_cell_volume                     1952.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9438
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.73
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            36983
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             4825
_reflns_number_gt                2949
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1224
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         4825
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.5941P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.42439(16) 0.29268(17) 0.39161(7) 0.0753(4) Uani d . . . 1 . .
O O2 0.49030(12) 0.64194(15) 0.24753(6) 0.0598(4) Uani d . . . 1 . .
O O4 0.10130(14) 0.56176(15) 0.33540(7) 0.0647(4) Uani d . . . 1 . .
N N1 0.28877(15) 0.85615(16) 0.28643(7) 0.0502(4) Uani d . . . 1 . .
N N2 0.47932(14) 0.48342(16) 0.33024(7) 0.0449(4) Uani d . . . 1 . .
N N4 0.21554(13) 0.72544(15) 0.28809(6) 0.0419(3) Uani d . . . 1 . .
C C1 0.04997(18) 0.7446(2) 0.19238(9) 0.0561(5) Uani d . . . 1 . .
H H1 0.021714 0.832039 0.209154 0.067000 Uiso calc U . R 1 . .
C C2 -0.0150(2) 0.6939(3) 0.13418(10) 0.0668(6) Uani d . . . 1 . .
H H2 -0.087801 0.745658 0.111758 0.080000 Uiso calc U . R 1 . .
C C3 0.0286(2) 0.5665(3) 0.10963(10) 0.0699(6) Uani d . . . 1 . .
H H3 -0.015413 0.530773 0.070469 0.084000 Uiso calc U . R 1 . .
C C4 0.1377(2) 0.4902(2) 0.14251(9) 0.0580(5) Uani d . . . 1 . .
H H4 0.166716 0.404618 0.124714 0.070000 Uiso calc U . R 1 . .
C C5 0.20500(16) 0.53879(19) 0.20166(8) 0.0425(4) Uani d . . . 1 . .
C C6 0.32793(19) 0.9250(2) 0.33932(9) 0.0530(5) Uani d . . . 1 . .
H H6 0.378914 1.011082 0.339158 0.064000 Uiso calc U . R 1 . .
C C7 0.29923(17) 0.87967(19) 0.39844(8) 0.0444(4) Uani d . . . 1 . .
C C8 0.22396(16) 0.75078(18) 0.39953(8) 0.0428(4) Uani d . . . 1 . .
C C9 0.17439(17) 0.67062(19) 0.34008(9) 0.0452(4) Uani d . . . 1 . .
C C10 0.32143(16) 0.44767(19) 0.23604(8) 0.0451(4) Uani d . . . 1 . .
H H10 0.351515 0.386120 0.204246 0.054000 Uiso calc U . R 1 . .
C C11 0.29380(17) 0.3399(2) 0.28684(9) 0.0519(5) Uani d . . . 1 . .
H H11A 0.209864 0.363077 0.297377 0.062000 Uiso calc U . R 1 . .
H H11B 0.292098 0.236347 0.272287 0.062000 Uiso calc U . R 1 . .
C C12 0.40258(19) 0.3628(2) 0.34243(9) 0.0509(5) Uani d . . . 1 . .
C C13 0.43795(16) 0.5399(2) 0.26934(8) 0.0441(4) Uani d . . . 1 . .
C C14 0.3427(2) 0.9609(2) 0.45440(10) 0.0598(5) Uani d . . . 1 . .
H H14 0.391346 1.048786 0.454189 0.072000 Uiso calc U . R 1 . .
C C15 0.3130(2) 0.9097(3) 0.50967(10) 0.0690(6) Uani d . . . 1 . .
H H15 0.341707 0.963110 0.546998 0.083000 Uiso calc U . R 1 . .
C C16 0.2407(2) 0.7793(3) 0.51004(10) 0.0685(6) Uani d . . . 1 . .
H H16 0.223162 0.744215 0.547905 0.082000 Uiso calc U . R 1 . .
C C17 0.19456(19) 0.7008(2) 0.45529(9) 0.0563(5) Uani d . . . 1 . .
H H17 0.143876 0.614554 0.455742 0.068000 Uiso calc U . R 1 . .
C C18 0.59343(17) 0.53775(19) 0.37389(8) 0.0455(4) Uani d . . . 1 . .
C C19 0.5812(2) 0.5986(2) 0.43110(9) 0.0595(5) Uani d . . . 1 . .
H H19 0.499309 0.604275 0.441749 0.071000 Uiso calc U . R 1 . .
C C20 0.6925(2) 0.6511(2) 0.47245(10) 0.0679(6) Uani d . . . 1 . .
H H20 0.685355 0.692192 0.511126 0.081000 Uiso calc U . R 1 . .
C C21 0.8134(2) 0.6425(2) 0.45642(10) 0.0663(6) Uani d . . . 1 . .
H H21 0.887788 0.678353 0.484182 0.080000 Uiso calc U . R 1 . .
C C22 0.8245(2) 0.5813(2) 0.39974(10) 0.0618(5) Uani d . . . 1 . .
H H22 0.906463 0.575211 0.389175 0.074000 Uiso calc U . R 1 . .
C C23 0.71437(18) 0.5285(2) 0.35819(9) 0.0523(5) Uani d . . . 1 . .
H H23 0.722057 0.486845 0.319697 0.063000 Uiso calc U . R 1 . .
C C25 0.15701(16) 0.66666(19) 0.22622(8) 0.0418(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . 1.212(2) ?
O2 C13 . 1.203(2) ?
O4 C9 . 1.220(2) ?
N1 C6 . 1.285(2) ?
N1 N4 . 1.3919(19) ?
N2 C13 . 1.391(2) ?
N2 C12 . 1.393(2) ?
N2 C18 . 1.436(2) ?
N4 C9 . 1.374(2) ?
N4 C25 . 1.446(2) ?
C1 C2 . 1.373(3) ?
C1 C25 . 1.382(2) ?
C2 C3 . 1.366(3) ?
C3 C4 . 1.382(3) ?
C4 C5 . 1.392(2) ?
C5 C25 . 1.389(2) ?
C5 C10 . 1.515(2) ?
C6 C7 . 1.432(2) ?
C7 C8 . 1.389(2) ?
C7 C14 . 1.400(3) ?
C8 C17 . 1.379(2) ?
C8 C9 . 1.465(2) ?
C10 C13 . 1.513(2) ?
C10 C11 . 1.529(2) ?
C11 C12 . 1.482(3) ?
C14 C15 . 1.374(3) ?
C15 C16 . 1.380(3) ?
C16 C17 . 1.371(3) ?
C18 C23 . 1.373(2) ?
C18 C19 . 1.381(2) ?
C19 C20 . 1.386(3) ?
C20 C21 . 1.376(3) ?
C21 C22 . 1.368(3) ?
C22 C23 . 1.381(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 N4 . . 116.44(14) ?
C13 N2 C12 . . 112.40(15) ?
C13 N2 C18 . . 123.40(14) ?
C12 N2 C18 . . 124.09(15) ?
C9 N4 N1 . . 125.62(14) ?
C9 N4 C25 . . 119.17(14) ?
N1 N4 C25 . . 113.73(13) ?
C2 C1 C25 . . 120.53(18) ?
C3 C2 C1 . . 119.18(19) ?
C2 C3 C4 . . 120.6(2) ?
C3 C4 C5 . . 121.41(19) ?
C25 C5 C4 . . 116.93(16) ?
C25 C5 C10 . . 124.22(16) ?
C4 C5 C10 . . 118.81(16) ?
N1 C6 C7 . . 125.15(17) ?
C8 C7 C14 . . 119.31(17) ?
C8 C7 C6 . . 118.11(16) ?
C14 C7 C6 . . 122.58(17) ?
C17 C8 C7 . . 120.63(17) ?
C17 C8 C9 . . 120.68(16) ?
C7 C8 C9 . . 118.67(15) ?
O4 C9 N4 . . 120.55(17) ?
O4 C9 C8 . . 123.69(16) ?
N4 C9 C8 . . 115.76(15) ?
C13 C10 C5 . . 115.02(14) ?
C13 C10 C11 . . 104.40(14) ?
C5 C10 C11 . . 115.76(14) ?
C12 C11 C10 . . 105.73(14) ?
O1 C12 N2 . . 123.48(18) ?
O1 C12 C11 . . 127.77(17) ?
N2 C12 C11 . . 108.74(15) ?
O2 C13 N2 . . 124.59(17) ?
O2 C13 C10 . . 127.12(16) ?
N2 C13 C10 . . 108.26(14) ?
C15 C14 C7 . . 119.47(19) ?
C14 C15 C16 . . 120.3(2) ?
C17 C16 C15 . . 120.8(2) ?
C16 C17 C8 . . 119.40(19) ?
C23 C18 C19 . . 120.50(18) ?
C23 C18 N2 . . 119.40(16) ?
C19 C18 N2 . . 120.10(16) ?
C18 C19 C20 . . 119.22(19) ?
C21 C20 C19 . . 120.14(19) ?
C22 C21 C20 . . 120.2(2) ?
C21 C22 C23 . . 120.21(19) ?
C18 C23 C22 . . 119.76(18) ?
C1 C25 C5 . . 121.33(16) ?
C1 C25 N4 . . 116.44(15) ?
C5 C25 N4 . . 122.23(15) ?

