# 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 2024

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

data_IPFAP
_database_code_depnum_ccdc_archive 'CCDC 2330349'
loop_
_audit_author_name
_audit_author_address
'Basavoju Srinivas'
;NATIONAL INSTITUTE OF TECHNOLOGY WARANGAL
India
;
_audit_update_record             
;
2024-02-01 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H29 F N4 O3'
_chemical_formula_weight         584.63

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/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                   11.1333(10)
_cell_length_b                   11.4934(10)
_cell_length_c                   22.104(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.270(4)
_cell_angle_gamma                90
_cell_volume                     2827.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            129193
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.067
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6169
_reflns_number_gt                5509
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0394P)²+1.7475P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0079(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6169
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.18467(14) 0.15435(13) 0.73290(7) 0.0273(3) Uani 1 1 d . . . . .
H1 H 0.1482 0.0902 0.7504 0.033 Uiso 1 1 calc R U . . .
C2 C 0.30829(14) 0.16240(14) 0.73193(8) 0.0306(3) Uani 1 1 d . . . . .
H6 H 0.3552 0.1021 0.7476 0.037 Uiso 1 1 calc R U . . .
C3 C 0.36329(13) 0.25986(13) 0.70780(7) 0.0259(3) Uani 1 1 d . . . . .
H5 H 0.4466 0.2656 0.7080 0.031 Uiso 1 1 calc R U . . .
C4 C 0.29308(11) 0.34837(11) 0.68341(6) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.46715(11) 0.47445(11) 0.65579(6) 0.0151(2) Uani 1 1 d . . . . .
H9 H 0.5295 0.4314 0.6734 0.018 Uiso 1 1 calc R U . . .
C6 C 0.47912(11) 0.57628(11) 0.62385(6) 0.0149(2) Uani 1 1 d . . . . .
C7 C 0.59423(11) 0.63325(11) 0.60531(6) 0.0143(2) Uani 1 1 d . . . . .
H26 H 0.5807 0.7174 0.6026 0.017 Uiso 1 1 calc R U . . .
C8 C 0.70064(11) 0.61146(11) 0.64907(6) 0.0142(2) Uani 1 1 d . . . . .
H27 H 0.7017 0.5292 0.6607 0.017 Uiso 1 1 calc R U . . .
C9 C 0.81255(11) 0.63799(11) 0.61003(6) 0.0153(3) Uani 1 1 d . . . . .
C10 C 0.86970(11) 0.75620(11) 0.62049(6) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.99181(12) 0.74025(12) 0.63340(6) 0.0190(3) Uani 1 1 d . . . . .
C12 C 1.06841(13) 0.83239(13) 0.64475(7) 0.0255(3) Uani 1 1 d . . . . .
H21 H 1.1496 0.8205 0.6535 0.031 Uiso 1 1 calc R U . . .
C13 C 1.01957(14) 0.94401(13) 0.64253(7) 0.0270(3) Uani 1 1 d . . . . .
H2 H 1.0694 1.0079 0.6492 0.032 Uiso 1 1 calc R U . . .
C14 C 0.90089(14) 0.62003(14) 0.86512(7) 0.0280(3) Uani 1 1 d . . . . .
C15 C 0.83002(14) 0.71864(13) 0.86209(7) 0.0266(3) Uani 1 1 d . . . . .
H29 H 0.8271 0.7702 0.8945 0.032 Uiso 1 1 calc R U . . .
C16 C 0.76357(13) 0.73845(12) 0.80951(6) 0.0213(3) Uani 1 1 d . . . . .
H28 H 0.7148 0.8040 0.8065 0.026 Uiso 1 1 calc R U . . .
C17 C 0.76892(12) 0.66078(11) 0.76063(6) 0.0179(3) Uani 1 1 d . . . . .
C18 C 0.84127(12) 0.56207(12) 0.76566(6) 0.0204(3) Uani 1 1 d . . . . .
H3 H 0.8447 0.5099 0.7336 0.025 Uiso 1 1 calc R U . . .
C19 C 0.90839(13) 0.54116(13) 0.81842(7) 0.0258(3) Uani 1 1 d . . . . .
H4 H 0.9570 0.4756 0.8220 0.031 Uiso 1 1 calc R U . . .
C20 C 0.69205(11) 0.68629(11) 0.70600(6) 0.0158(3) Uani 1 1 d . . . . .
C21 C 0.35952(11) 0.60669(11) 0.60685(6) 0.0157(3) Uani 1 1 d . . . . .
C22 C 0.11554(14) 0.24235(14) 0.70767(8) 0.0308(4) Uani 1 1 d . . . . .
H8 H 0.0322 0.2366 0.7076 0.037 Uiso 1 1 calc R U . . .
C23 C 0.16911(13) 0.33919(13) 0.68247(7) 0.0268(3) Uani 1 1 d . . . . .
H7 H 0.1221 0.3976 0.6650 0.032 Uiso 1 1 calc R U . . .
C24 C 0.31360(11) 0.70717(12) 0.57173(6) 0.0190(3) Uani 1 1 d . . . . .
C25 C 0.35561(13) 0.81908(12) 0.58408(7) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.4157 0.8303 0.6134 0.030 Uiso 1 1 calc R U . . .
C26 C 0.30807(14) 0.91398(14) 0.55275(9) 0.0342(4) Uani 1 1 d . . . . .
H14 H 0.3367 0.9885 0.5609 0.041 Uiso 1 1 calc R U . . .
C27 C 0.21794(15) 0.89743(15) 0.50936(8) 0.0372(4) Uani 1 1 d . . . . .
H11 H 0.1851 0.9611 0.4890 0.045 Uiso 1 1 calc R U . . .
C28 C 0.17670(14) 0.78659(15) 0.49631(7) 0.0323(4) Uani 1 1 d . . . . .
H13 H 0.1167 0.7760 0.4669 0.039 Uiso 1 1 calc R U . . .
C29 C 0.22442(13) 0.69087(13) 0.52693(7) 0.0239(3) Uani 1 1 d . . . . .
H12 H 0.1972 0.6163 0.5177 0.029 Uiso 1 1 calc R U . . .
C30 C 0.64115(11) 0.59068(11) 0.54437(6) 0.0168(3) Uani 1 1 d . . . . .
H25 H 0.6237 0.5077 0.5390 0.020 Uiso 1 1 calc R U . . .
C31 C 0.59594(12) 0.65985(13) 0.48876(6) 0.0221(3) Uani 1 1 d . . . . .
H15 H 0.5870 0.6096 0.4537 0.027 Uiso 1 1 calc R U . . .
H24 H 0.5193 0.6965 0.4965 0.027 Uiso 1 1 calc R U . . .
C32 C 0.69358(14) 0.75120(13) 0.47908(7) 0.0245(3) Uani 1 1 d . . . . .
H23 H 0.6954 0.7758 0.4371 0.029 Uiso 1 1 calc R U . . .
H16 H 0.6820 0.8187 0.5046 0.029 Uiso 1 1 calc R U . . .
C33 C 0.80737(13) 0.68539(13) 0.49731(6) 0.0236(3) Uani 1 1 d . . . . .
H17 H 0.8360 0.6394 0.4638 0.028 Uiso 1 1 calc R U . . .
H18 H 0.8703 0.7389 0.5102 0.028 Uiso 1 1 calc R U . . .
C34 C 0.91952(11) 0.55421(11) 0.62442(6) 0.0168(3) Uani 1 1 d . . . . .
C35 C 0.89818(14) 0.96176(12) 0.63052(7) 0.0242(3) Uani 1 1 d . . . . .
H20 H 0.8673 1.0369 0.6299 0.029 Uiso 1 1 calc R U . . .
C36 C 0.82224(12) 0.86734(12) 0.61931(6) 0.0193(3) Uani 1 1 d . . . . .
H19 H 0.7408 0.8790 0.6111 0.023 Uiso 1 1 calc R U . . .
F1 F 0.96539(10) 0.59960(9) 0.91659(5) 0.0421(3) Uani 1 1 d . . . . .
N1 N 0.34834(9) 0.44775(9) 0.65723(5) 0.0146(2) Uani 1 1 d . . . . .
N2 N 0.28052(9) 0.52863(9) 0.62729(5) 0.0153(2) Uani 1 1 d . . . . .
N3 N 0.77220(10) 0.60993(10) 0.54766(5) 0.0172(2) Uani 1 1 d . . . . .
N4 N 1.01968(10) 0.62049(10) 0.63355(6) 0.0205(3) Uani 1 1 d . . . . .
H22 H 1.0909 0.5928 0.6387 0.025 Uiso 1 1 calc R U . . .
O2 O 0.91347(9) 0.44858(8) 0.62591(5) 0.0221(2) Uani 1 1 d . . . . .
O3 O 0.62143(9) 0.76728(8) 0.70689(4) 0.0217(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(2) . ?
C1 C22 1.381(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(2) . ?
C2 H6 0.9300 . ?
C3 C4 1.3848(19) . ?
C3 H5 0.9300 . ?
C4 C23 1.3839(19) . ?
C4 N1 1.4262(16) . ?
C5 N1 1.3590(16) . ?
C5 C6 1.3748(18) . ?
C5 H9 0.9300 . ?
C6 C21 1.4192(17) . ?
C6 C7 1.5041(17) . ?
C7 C8 1.5334(17) . ?
C7 C30 1.5356(17) . ?
C7 H26 0.9800 . ?
C8 C20 1.5289(18) . ?
C8 C9 1.5613(17) . ?
C8 H27 0.9800 . ?
C9 N3 1.4760(17) . ?
C9 C10 1.5158(18) . ?
C9 C34 1.5588(17) . ?
C10 C36 1.3824(18) . ?
C10 C11 1.3949(19) . ?
C11 C12 1.3793(19) . ?
C11 N4 1.4110(17) . ?
C12 C13 1.394(2) . ?
C12 H21 0.9300 . ?
C13 C35 1.387(2) . ?
C13 H2 0.9300 . ?
C14 F1 1.3523(17) . ?
C14 C19 1.378(2) . ?
C14 C15 1.382(2) . ?
C15 C16 1.383(2) . ?
C15 H29 0.9300 . ?
C16 C17 1.4038(19) . ?
C16 H28 0.9300 . ?
C17 C18 1.3944(19) . ?
C17 C20 1.4936(18) . ?
C18 C19 1.392(2) . ?
C18 H3 0.9300 . ?
C19 H4 0.9300 . ?
C20 O3 1.2188(16) . ?
C21 N2 1.3418(16) . ?
C21 C24 1.4765(18) . ?
C22 C23 1.386(2) . ?
C22 H8 0.9300 . ?
C23 H7 0.9300 . ?
C24 C25 1.394(2) . ?
C24 C29 1.399(2) . ?
C25 C26 1.390(2) . ?
C25 H10 0.9300 . ?
C26 C27 1.386(3) . ?
C26 H14 0.9300 . ?
C27 C28 1.382(3) . ?
C27 H11 0.9300 . ?
C28 C29 1.391(2) . ?
C28 H13 0.9300 . ?
C29 H12 0.9300 . ?
C30 N3 1.4758(16) . ?
C30 C31 1.5390(19) . ?
C30 H25 0.9800 . ?
C31 C32 1.530(2) . ?
C31 H15 0.9700 . ?
C31 H24 0.9700 . ?
C32 C33 1.522(2) . ?
C32 H23 0.9700 . ?
C32 H16 0.9700 . ?
C33 N3 1.4710(17) . ?
C33 H17 0.9700 . ?
C33 H18 0.9700 . ?
C34 O2 1.2165(16) . ?
C34 N4 1.3617(17) . ?
C35 C36 1.3946(19) . ?
C35 H20 0.9300 . ?
C36 H19 0.9300 . ?
N1 N2 1.3602(15) . ?
N4 H22 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C22 119.45(13) . . ?
C2 C1 H1 120.3 . . ?
C22 C1 H1 120.3 . . ?
C1 C2 C3 120.56(14) . . ?
C1 C2 H6 119.7 . . ?
C3 C2 H6 119.7 . . ?
C4 C3 C2 119.48(13) . . ?
C4 C3 H5 120.3 . . ?
C2 C3 H5 120.3 . . ?
C23 C4 C3 120.27(12) . . ?
C23 C4 N1 119.60(12) . . ?
C3 C4 N1 120.10(12) . . ?
N1 C5 C6 108.04(11) . . ?
N1 C5 H9 126.0 . . ?
C6 C5 H9 126.0 . . ?
C5 C6 C21 104.16(11) . . ?
C5 C6 C7 127.11(11) . . ?
C21 C6 C7 128.37(11) . . ?
C6 C7 C8 114.08(10) . . ?
C6 C7 C30 114.13(10) . . ?
C8 C7 C30 103.19(10) . . ?
C6 C7 H26 108.4 . . ?
C8 C7 H26 108.4 . . ?
C30 C7 H26 108.4 . . ?
C20 C8 C7 111.45(10) . . ?
C20 C8 C9 114.23(10) . . ?
C7 C8 C9 103.55(10) . . ?
C20 C8 H27 109.1 . . ?
C7 C8 H27 109.1 . . ?
C9 C8 H27 109.1 . . ?
N3 C9 C10 117.15(11) . . ?
N3 C9 C34 105.72(10) . . ?
C10 C9 C34 101.90(10) . . ?
N3 C9 C8 104.09(10) . . ?
C10 C9 C8 115.35(10) . . ?
C34 C9 C8 112.46(10) . . ?
C36 C10 C11 119.72(12) . . ?
C36 C10 C9 131.79(12) . . ?
C11 C10 C9 108.50(11) . . ?
C12 C11 C10 122.15(13) . . ?
C12 C11 N4 127.85(13) . . ?
C10 C11 N4 110.00(12) . . ?
C11 C12 C13 117.46(13) . . ?
C11 C12 H21 121.3 . . ?
C13 C12 H21 121.3 . . ?
C35 C13 C12 121.33(13) . . ?
C35 C13 H2 119.3 . . ?
C12 C13 H2 119.3 . . ?
F1 C14 C19 118.44(14) . . ?
F1 C14 C15 118.37(14) . . ?
C19 C14 C15 123.19(14) . . ?
C14 C15 C16 118.04(14) . . ?
C14 C15 H29 121.0 . . ?
C16 C15 H29 121.0 . . ?
C15 C16 C17 120.74(13) . . ?
C15 C16 H28 119.6 . . ?
C17 C16 H28 119.6 . . ?
C18 C17 C16 119.36(13) . . ?
C18 C17 C20 122.95(12) . . ?
C16 C17 C20 117.65(12) . . ?
C19 C18 C17 120.38(13) . . ?
C19 C18 H3 119.8 . . ?
C17 C18 H3 119.8 . . ?
C14 C19 C18 118.28(14) . . ?
C14 C19 H4 120.9 . . ?
C18 C19 H4 120.9 . . ?
O3 C20 C17 119.68(12) . . ?
O3 C20 C8 119.68(12) . . ?
C17 C20 C8 120.65(11) . . ?
N2 C21 C6 111.37(11) . . ?
N2 C21 C24 118.56(11) . . ?
C6 C21 C24 130.07(12) . . ?
C1 C22 C23 120.64(14) . . ?
C1 C22 H8 119.7 . . ?
C23 C22 H8 119.7 . . ?
C4 C23 C22 119.55(14) . . ?
C4 C23 H7 120.2 . . ?
C22 C23 H7 120.2 . . ?
C25 C24 C29 119.48(13) . . ?
C25 C24 C21 120.54(13) . . ?
C29 C24 C21 119.96(13) . . ?
C26 C25 C24 120.27(15) . . ?
C26 C25 H10 119.9 . . ?
C24 C25 H10 119.9 . . ?
C27 C26 C25 119.92(15) . . ?
C27 C26 H14 120.0 . . ?
C25 C26 H14 120.0 . . ?
C28 C27 C26 120.20(14) . . ?
C28 C27 H11 119.9 . . ?
C26 C27 H11 119.9 . . ?
C27 C28 C29 120.39(15) . . ?
C27 C28 H13 119.8 . . ?
C29 C28 H13 119.8 . . ?
C28 C29 C24 119.72(15) . . ?
C28 C29 H12 120.1 . . ?
C24 C29 H12 120.1 . . ?
N3 C30 C7 105.32(10) . . ?
N3 C30 C31 105.51(10) . . ?
C7 C30 C31 115.10(11) . . ?
N3 C30 H25 110.2 . . ?
C7 C30 H25 110.2 . . ?
C31 C30 H25 110.2 . . ?
C32 C31 C30 104.20(11) . . ?
C32 C31 H15 110.9 . . ?
C30 C31 H15 110.9 . . ?
C32 C31 H24 110.9 . . ?
C30 C31 H24 110.9 . . ?
H15 C31 H24 108.9 . . ?
C33 C32 C31 102.23(11) . . ?
C33 C32 H23 111.3 . . ?
C31 C32 H23 111.3 . . ?
C33 C32 H16 111.3 . . ?
C31 C32 H16 111.3 . . ?
H23 C32 H16 109.2 . . ?
N3 C33 C32 105.03(11) . . ?
N3 C33 H17 110.7 . . ?
C32 C33 H17 110.7 . . ?
N3 C33 H18 110.7 . . ?
C32 C33 H18 110.7 . . ?
H17 C33 H18 108.8 . . ?
O2 C34 N4 126.87(12) . . ?
O2 C34 C9 125.41(12) . . ?
N4 C34 C9 107.71(11) . . ?
C13 C35 C36 120.27(13) . . ?
C13 C35 H20 119.9 . . ?
C36 C35 H20 119.9 . . ?
C10 C36 C35 119.06(13) . . ?
C10 C36 H19 120.5 . . ?
C35 C36 H19 120.5 . . ?
C5 N1 N2 111.37(10) . . ?
C5 N1 C4 128.26(11) . . ?
N2 N1 C4 120.33(10) . . ?
C21 N2 N1 105.06(10) . . ?
C33 N3 C30 109.30(10) . . ?
C33 N3 C9 119.82(11) . . ?
C30 N3 C9 111.03(10) . . ?
C34 N4 C11 111.47(11) . . ?
C34 N4 H22 124.3 . . ?
C11 N4 H22 124.3 . . ?

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
C22 C1 C2 C3 2.3(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C23 -0.7(2) . . . . ?
C2 C3 C4 N1 -178.56(14) . . . . ?
N1 C5 C6 C21 -0.04(14) . . . . ?
N1 C5 C6 C7 -173.56(12) . . . . ?
C5 C6 C7 C8 -30.55(18) . . . . ?
C21 C6 C7 C8 157.47(13) . . . . ?
C5 C6 C7 C30 87.75(16) . . . . ?
C21 C6 C7 C30 -84.23(16) . . . . ?
C6 C7 C8 C20 -76.54(13) . . . . ?
C30 C7 C8 C20 159.08(10) . . . . ?
C6 C7 C8 C9 160.22(10) . . . . ?
C30 C7 C8 C9 35.84(12) . . . . ?
C20 C8 C9 N3 -150.30(10) . . . . ?
C7 C8 C9 N3 -28.91(12) . . . . ?
C20 C8 C9 C10 -20.54(15) . . . . ?
C7 C8 C9 C10 100.85(12) . . . . ?
C20 C8 C9 C34 95.74(13) . . . . ?
C7 C8 C9 C34 -142.87(11) . . . . ?
N3 C9 C10 C36 69.89(18) . . . . ?
C34 C9 C10 C36 -175.32(14) . . . . ?
C8 C9 C10 C36 -53.19(19) . . . . ?
N3 C9 C10 C11 -110.29(13) . . . . ?
C34 C9 C10 C11 4.51(14) . . . . ?
C8 C9 C10 C11 126.64(12) . . . . ?
C36 C10 C11 C12 -0.5(2) . . . . ?
C9 C10 C11 C12 179.64(13) . . . . ?
C36 C10 C11 N4 178.64(12) . . . . ?
C9 C10 C11 N4 -1.20(15) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
N4 C11 C12 C13 -179.40(14) . . . . ?
C11 C12 C13 C35 1.2(2) . . . . ?
F1 C14 C15 C16 -179.48(13) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C15 C16 C17 C20 178.37(12) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C20 C17 C18 C19 -178.14(12) . . . . ?
F1 C14 C19 C18 179.58(13) . . . . ?
C15 C14 C19 C18 0.0(2) . . . . ?
C17 C18 C19 C14 0.2(2) . . . . ?
C18 C17 C20 O3 172.26(13) . . . . ?
C16 C17 C20 O3 -5.36(18) . . . . ?
C18 C17 C20 C8 -7.44(18) . . . . ?
C16 C17 C20 C8 174.94(11) . . . . ?
C7 C8 C20 O3 -13.82(16) . . . . ?
C9 C8 C20 O3 103.10(13) . . . . ?
C7 C8 C20 C17 165.88(11) . . . . ?
C9 C8 C20 C17 -77.20(14) . . . . ?
C5 C6 C21 N2 0.15(15) . . . . ?
C7 C6 C21 N2 173.56(12) . . . . ?
C5 C6 C21 C24 -179.90(13) . . . . ?
C7 C6 C21 C24 -6.5(2) . . . . ?
C2 C1 C22 C23 -1.1(3) . . . . ?
C3 C4 C23 C22 1.9(2) . . . . ?
N1 C4 C23 C22 179.70(14) . . . . ?
C1 C22 C23 C4 -0.9(3) . . . . ?
N2 C21 C24 C25 134.26(14) . . . . ?
C6 C21 C24 C25 -45.7(2) . . . . ?
N2 C21 C24 C29 -43.70(18) . . . . ?
C6 C21 C24 C29 136.35(15) . . . . ?
C29 C24 C25 C26 0.9(2) . . . . ?
C21 C24 C25 C26 -177.05(14) . . . . ?
C24 C25 C26 C27 0.5(2) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C27 C28 C29 0.6(3) . . . . ?
C27 C28 C29 C24 0.8(2) . . . . ?
C25 C24 C29 C28 -1.6(2) . . . . ?
C21 C24 C29 C28 176.42(13) . . . . ?
C6 C7 C30 N3 -154.01(10) . . . . ?
C8 C7 C30 N3 -29.66(12) . . . . ?
C6 C7 C30 C31 90.24(13) . . . . ?
C8 C7 C30 C31 -145.41(11) . . . . ?
N3 C30 C31 C32 -21.95(14) . . . . ?
C7 C30 C31 C32 93.70(13) . . . . ?
C30 C31 C32 C33 35.04(14) . . . . ?
C31 C32 C33 N3 -35.61(14) . . . . ?
N3 C9 C34 O2 -62.22(16) . . . . ?
C10 C9 C34 O2 174.84(13) . . . . ?
C8 C9 C34 O2 50.74(18) . . . . ?
N3 C9 C34 N4 116.52(11) . . . . ?
C10 C9 C34 N4 -6.42(13) . . . . ?
C8 C9 C34 N4 -130.52(12) . . . . ?
C12 C13 C35 C36 -1.1(2) . . . . ?
C11 C10 C36 C35 0.6(2) . . . . ?
C9 C10 C36 C35 -179.56(13) . . . . ?
C13 C35 C36 C10 0.1(2) . . . . ?
C6 C5 N1 N2 -0.07(14) . . . . ?
C6 C5 N1 C4 177.72(12) . . . . ?
C23 C4 N1 C5 177.22(13) . . . . ?
C3 C4 N1 C5 -4.9(2) . . . . ?
C23 C4 N1 N2 -5.16(19) . . . . ?
C3 C4 N1 N2 172.68(12) . . . . ?
C6 C21 N2 N1 -0.19(14) . . . . ?
C24 C21 N2 N1 179.85(11) . . . . ?
C5 N1 N2 C21 0.16(14) . . . . ?
C4 N1 N2 C21 -177.83(11) . . . . ?
C32 C33 N3 C30 22.79(14) . . . . ?
C32 C33 N3 C9 -106.93(13) . . . . ?
C7 C30 N3 C33 -122.57(11) . . . . ?
C31 C30 N3 C33 -0.39(14) . . . . ?
C7 C30 N3 C9 11.79(13) . . . . ?
C31 C30 N3 C9 133.97(11) . . . . ?
C10 C9 N3 C33 10.99(17) . . . . ?
C34 C9 N3 C33 -101.67(13) . . . . ?
C8 C9 N3 C33 139.66(11) . . . . ?
C10 C9 N3 C30 -117.95(12) . . . . ?
C34 C9 N3 C30 129.39(11) . . . . ?
C8 C9 N3 C30 10.72(13) . . . . ?
O2 C34 N4 C11 -175.09(14) . . . . ?
C9 C34 N4 C11 6.19(15) . . . . ?
C12 C11 N4 C34 175.79(14) . . . . ?
C10 C11 N4 C34 -3.30(16) . . . . ?

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
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666
N4 H22 N2 0.86 2.26 3.0959(15) 165.6 1_655
C19 H4 O3 0.93 2.62 3.2131(18) 121.9 2_646
C23 H7 O2 0.93 2.53 3.3296(18) 144.4 1_455
C31 H15 N1 0.97 2.65 3.5236(18) 149.5 3_666

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044

