# 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 2020

####################################################################### 
# 
# 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_SPA535
_database_code_depnum_ccdc_archive 'CCDC 2001136'
loop_
_audit_author_name
_audit_author_address
'Vedichi Madhu'
;Department of Chemistry, Karunya University
India
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-27 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         'C20 H28 N6'
_chemical_formula_sum            'C20 H28 N6'
_chemical_formula_weight         352.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 '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                   4.8930(10)
_cell_length_b                   10.170(2)
_cell_length_c                   18.638(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.05(3)
_cell_angle_gamma                90
_cell_volume                     927.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    26213
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8864
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.937
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2477
_reflns_number_gt                2125
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0821P)²+0.1140P] 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         2477
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
N1 N 0.16831(18) 0.52154(8) 0.58600(4) 0.0251(2) Uani 1 1 d . . . . .
N2 N 0.40825(18) 0.57034(8) 0.69117(4) 0.0263(2) Uani 1 1 d . . . . .
N3 N 0.58248(19) 0.48559(9) 0.83150(5) 0.0277(2) Uani 1 1 d . . . . .
C1 C 0.1067(2) 0.54366(9) 0.51640(5) 0.0246(2) Uani 1 1 d . . . . .
C2 C 0.2337(2) 0.64004(11) 0.47643(5) 0.0309(3) Uani 1 1 d . . . . .
H2 H 0.185927 0.653767 0.427927 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4333(2) 0.71558(11) 0.51029(6) 0.0336(3) Uani 1 1 d . . . . .
H3 H 0.524102 0.781309 0.484471 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4996(2) 0.69491(10) 0.58163(6) 0.0302(3) Uani 1 1 d . . . . .
H4 H 0.634339 0.745884 0.605047 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3600(2) 0.59556(10) 0.61831(5) 0.0238(2) Uani 1 1 d . . . . .
C6 C 0.6460(2) 0.63022(11) 0.72666(6) 0.0310(3) Uani 1 1 d . . . . .
H6A H 0.659881 0.722755 0.712502 0.037 Uiso 1 1 calc R U . . .
H6AB H 0.812679 0.585071 0.711832 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6193(2) 0.62060(11) 0.80742(6) 0.0327(3) Uani 1 1 d . . . . .
H7A H 0.783829 0.657222 0.830590 0.039 Uiso 1 1 calc R U . . .
H7AB H 0.462770 0.673437 0.822318 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3395(2) 0.43064(11) 0.79628(6) 0.0328(3) Uani 1 1 d . . . . .
H8A H 0.178063 0.480148 0.810997 0.039 Uiso 1 1 calc R U . . .
H8AB H 0.316278 0.339122 0.811456 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3610(3) 0.43592(11) 0.71576(6) 0.0332(3) Uani 1 1 d . . . . .
H9A H 0.511835 0.379564 0.700622 0.040 Uiso 1 1 calc R U . . .
H9AB H 0.191774 0.402226 0.693640 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5547(3) 0.48281(13) 0.90927(6) 0.0395(3) Uani 1 1 d . . . . .
H10A H 0.518443 0.393492 0.924687 0.059 Uiso 1 1 calc R U . . .
H10B H 0.404499 0.539264 0.922888 0.059 Uiso 1 1 calc R U . . .
H10C H 0.722633 0.513816 0.931965 0.059 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
N1 C5 1.3374(13) . ?
N1 C1 1.3454(12) . ?
N2 C5 1.3978(12) . ?
N2 C6 1.4608(13) . ?
N2 C9 1.4616(13) . ?
N3 C7 1.4567(14) . ?
N3 C10 1.4586(14) . ?
N3 C8 1.4588(14) . ?
C1 C2 1.3851(15) . ?
C1 C1 1.493(2) 3_566 ?
C2 C3 1.3856(16) . ?
C2 H2 0.9400 . ?
C3 C4 1.3790(15) . ?
C3 H3 0.9400 . ?
C4 C5 1.4041(15) . ?
C4 H4 0.9400 . ?
C6 C7 1.5165(15) . ?
C6 H6A 0.9800 . ?
C6 H6AB 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7AB 0.9800 . ?
C8 C9 1.5074(15) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 118.88(9) . . ?
C5 N2 C6 118.84(9) . . ?
C5 N2 C9 116.83(8) . . ?
C6 N2 C9 112.16(8) . . ?
C7 N3 C10 109.80(9) . . ?
C7 N3 C8 109.08(8) . . ?
C10 N3 C8 110.47(10) . . ?
N1 C1 C2 122.83(9) . . ?
N1 C1 C1 115.97(11) . 3_566 ?
C2 C1 C1 121.20(11) . 3_566 ?
C1 C2 C3 117.83(10) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.39(10) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.12(10) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 N2 116.02(9) . . ?
N1 C5 C4 121.95(9) . . ?
N2 C5 C4 122.01(9) . . ?
N2 C6 C7 109.89(9) . . ?
N2 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N2 C6 H6AB 109.7 . . ?
C7 C6 H6AB 109.7 . . ?
H6A C6 H6AB 108.2 . . ?
N3 C7 C6 112.34(8) . . ?
N3 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N3 C7 H7AB 109.1 . . ?
C6 C7 H7AB 109.1 . . ?
H7A C7 H7AB 107.9 . . ?
N3 C8 C9 111.30(10) . . ?
N3 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N3 C8 H8AB 109.4 . . ?
C9 C8 H8AB 109.4 . . ?
H8A C8 H8AB 108.0 . . ?
N2 C9 C8 111.09(9) . . ?
N2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N2 C9 H9AB 109.4 . . ?
C8 C9 H9AB 109.4 . . ?
H9A C9 H9AB 108.0 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.06(16) . . . . ?
C5 N1 C1 C1 179.31(10) . . . 3_566 ?
N1 C1 C2 C3 0.38(17) . . . . ?
C1 C1 C2 C3 -178.83(11) 3_566 . . . ?
C1 C2 C3 C4 -0.49(17) . . . . ?
C2 C3 C4 C5 0.20(18) . . . . ?
C1 N1 C5 N2 178.07(9) . . . . ?
C1 N1 C5 C4 -0.38(16) . . . . ?
C6 N2 C5 N1 169.19(9) . . . . ?
C9 N2 C5 N1 29.63(13) . . . . ?
C6 N2 C5 C4 -12.36(15) . . . . ?
C9 N2 C5 C4 -151.92(11) . . . . ?
C3 C4 C5 N1 0.25(17) . . . . ?
C3 C4 C5 N2 -178.10(10) . . . . ?
C5 N2 C6 C7 165.09(9) . . . . ?
C9 N2 C6 C7 -53.59(12) . . . . ?
C10 N3 C7 C6 -179.29(9) . . . . ?
C8 N3 C7 C6 -58.11(12) . . . . ?
N2 C6 C7 N3 56.13(12) . . . . ?
C7 N3 C8 C9 57.72(12) . . . . ?
C10 N3 C8 C9 178.49(9) . . . . ?
C5 N2 C9 C8 -163.38(9) . . . . ?
C6 N2 C9 C8 54.47(13) . . . . ?
N3 C8 C9 N2 -56.47(13) . . . . ?

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_SPA259
_database_code_depnum_ccdc_archive 'CCDC 2001137'
loop_
_audit_author_name
_audit_author_address
'Vedichi Madhu'
;Department of Chemistry, Karunya University
India
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-27 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         'C18 H22 N4'
_chemical_formula_sum            'C18 H22 N4'
_chemical_formula_weight         294.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 '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                   7.0750(14)
_cell_length_b                   7.3030(15)
_cell_length_c                   14.865(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.04(3)
_cell_angle_gamma                90
_cell_volume                     763.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    23420
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7266
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         25.487
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1987
_reflns_number_gt                1756
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0914P)²+0.0679P] 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         1987
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
N1 N 0.43310(11) 0.50155(10) 0.37938(5) 0.0252(2) Uani 1 1 d . . . . .
N2 N 0.39235(12) 0.50618(12) 0.22370(6) 0.0321(2) Uani 1 1 d . . . . .
C1 C 0.54662(12) 0.51479(11) 0.45769(6) 0.0239(2) Uani 1 1 d . . . . .
C2 C 0.73970(12) 0.55280(14) 0.46211(6) 0.0304(2) Uani 1 1 d . . . . .
H2 H 0.814893 0.561817 0.517959 0.037 Uiso 1 1 calc R U . . .
C3 C 0.81806(12) 0.57714(15) 0.38058(6) 0.0342(3) Uani 1 1 d . . . . .
H3 H 0.948365 0.602879 0.381203 0.041 Uiso 1 1 calc R U . . .
C4 C 0.70647(12) 0.56380(14) 0.29954(6) 0.0320(2) Uani 1 1 d . . . . .
H4 H 0.758319 0.580385 0.244435 0.038 Uiso 1 1 calc R U . . .
C5 C 0.51093(12) 0.52433(12) 0.30136(6) 0.0255(2) Uani 1 1 d . . . . .
C6 C 0.18581(13) 0.49120(13) 0.22349(7) 0.0309(2) Uani 1 1 d . . . . .
H6A H 0.136216 0.590207 0.258807 0.037 Uiso 1 1 calc R U . . .
H6AB H 0.150766 0.373384 0.248583 0.037 Uiso 1 1 calc R U . . .
C7 C 0.11007(15) 0.50655(15) 0.12382(7) 0.0351(3) Uani 1 1 d . . . . .
H7A H 0.004618 0.421152 0.108785 0.042 Uiso 1 1 calc R U . . .
H7AB H 0.065993 0.631274 0.109117 0.042 Uiso 1 1 calc R U . . .
C8 C 0.27912(15) 0.45751(17) 0.07298(7) 0.0396(3) Uani 1 1 d . . . . .
H8A H 0.268913 0.516503 0.013456 0.048 Uiso 1 1 calc R U . . .
H8AB H 0.288150 0.324710 0.064976 0.048 Uiso 1 1 calc R U . . .
C9 C 0.45017(14) 0.53000(15) 0.13336(6) 0.0331(2) Uani 1 1 d . . . . .
H9A H 0.564795 0.458913 0.125580 0.040 Uiso 1 1 calc R U . . .
H9AB H 0.473717 0.659236 0.120715 0.040 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
N1 C5 1.3454(12) . ?
N1 C1 1.3464(13) . ?
N2 C5 1.3602(13) . ?
N2 C9 1.4549(12) . ?
N2 C6 1.4650(12) . ?
C1 C2 1.3887(12) . ?
C1 C1 1.4962(17) 3_666 ?
C2 C3 1.3961(13) . ?
C2 H2 0.9400 . ?
C3 C4 1.3725(14) . ?
C3 H3 0.9400 . ?
C4 C5 1.4162(12) . ?
C4 H4 0.9400 . ?
C6 C7 1.5256(14) . ?
C6 H6A 0.9800 . ?
C6 H6AB 0.9800 . ?
C7 C8 1.5232(16) . ?
C7 H7A 0.9800 . ?
C7 H7AB 0.9800 . ?
C8 C9 1.5236(15) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 118.38(8) . . ?
C5 N2 C9 124.30(8) . . ?
C5 N2 C6 122.35(8) . . ?
C9 N2 C6 112.60(8) . . ?
N1 C1 C2 123.33(9) . . ?
N1 C1 C1 116.15(9) . 3_666 ?
C2 C1 C1 120.51(10) . 3_666 ?
C1 C2 C3 117.58(9) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.57(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.06(9) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
N1 C5 N2 116.59(8) . . ?
N1 C5 C4 122.07(9) . . ?
N2 C5 C4 121.34(9) . . ?
N2 C6 C7 104.18(9) . . ?
N2 C6 H6A 110.9 . . ?
C7 C6 H6A 110.9 . . ?
N2 C6 H6AB 110.9 . . ?
C7 C6 H6AB 110.9 . . ?
H6A C6 H6AB 108.9 . . ?
C8 C7 C6 104.52(8) . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7AB 110.8 . . ?
C6 C7 H7AB 110.8 . . ?
H7A C7 H7AB 108.9 . . ?
C7 C8 C9 104.03(8) . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8AB 110.9 . . ?
C9 C8 H8AB 110.9 . . ?
H8A C8 H8AB 109.0 . . ?
N2 C9 C8 102.65(8) . . ?
N2 C9 H9A 111.2 . . ?
C8 C9 H9A 111.2 . . ?
N2 C9 H9AB 111.2 . . ?
C8 C9 H9AB 111.2 . . ?
H9A C9 H9AB 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.74(14) . . . . ?
C5 N1 C1 C1 -179.02(8) . . . 3_666 ?
N1 C1 C2 C3 -0.37(14) . . . . ?
C1 C1 C2 C3 179.38(10) 3_666 . . . ?
C1 C2 C3 C4 0.08(15) . . . . ?
C2 C3 C4 C5 -0.18(16) . . . . ?
C1 N1 C5 N2 178.69(7) . . . . ?
C1 N1 C5 C4 -0.83(13) . . . . ?
C9 N2 C5 N1 178.58(8) . . . . ?
C6 N2 C5 N1 9.29(13) . . . . ?
C9 N2 C5 C4 -1.89(15) . . . . ?
C6 N2 C5 C4 -171.18(9) . . . . ?
C3 C4 C5 N1 0.57(14) . . . . ?
C3 C4 C5 N2 -178.93(9) . . . . ?
C5 N2 C6 C7 170.64(9) . . . . ?
C9 N2 C6 C7 0.22(11) . . . . ?
N2 C6 C7 C8 20.73(11) . . . . ?
C6 C7 C8 C9 -33.49(11) . . . . ?
C5 N2 C9 C8 168.90(9) . . . . ?
C6 N2 C9 C8 -20.89(11) . . . . ?
C7 C8 C9 N2 32.90(11) . . . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_SPA538
_database_code_depnum_ccdc_archive 'CCDC 2001138'
loop_
_audit_author_name
_audit_author_address
'Vedichi Madhu'
;Department of Chemistry, Karunya University
India
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-27 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         'C18 H23 N4 O2, P F6'
_chemical_formula_sum            'C18 H23 F6 N4 O2 P'
_chemical_formula_weight         472.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0134 0.0079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0833 0.0744 '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                   7.1800(14)
_cell_length_b                   14.821(3)
_cell_length_c                   19.057(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.31(3)
_cell_angle_gamma                90
_cell_volume                     2006.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    84890
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18607
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.549
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             5207
_reflns_number_gt                3022
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.2000P)²] 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         5207
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1510
_refine_ls_R_factor_gt           0.1179
_refine_ls_wR_factor_ref         0.3195
_refine_ls_wR_factor_gt          0.3022
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0470(6) 0.6118(3) 0.15797(17) 0.0571(10) Uani 1 1 d . . . . .
O2 O 0.2317(5) 0.9596(2) 0.49655(19) 0.0476(8) Uani 1 1 d . . . . .
N1 N 0.1554(4) 0.5193(2) 0.40724(16) 0.0278(7) Uani 1 1 d . . . . .
N2 N 0.0260(5) 0.5196(2) 0.28916(17) 0.0358(8) Uani 1 1 d . . . . .
N3 N 0.2863(4) 0.62493(19) 0.50977(17) 0.0273(7) Uani 1 1 d . . . . .
H3N3 H 0.240103 0.638815 0.466383 0.033 Uiso 1 1 calc R U . . .
N4 N 0.3189(5) 0.7789(2) 0.53224(18) 0.0350(8) Uani 1 1 d . . . . .
C1 C 0.2077(5) 0.4755(2) 0.46884(19) 0.0258(7) Uani 1 1 d . . . . .
C2 C 0.1868(6) 0.3836(2) 0.4781(2) 0.0332(9) Uani 1 1 d . . . . .
H2 H 0.223571 0.355734 0.522275 0.040 Uiso 1 1 calc R U . . .
C3 C 0.1087(6) 0.3345(3) 0.4188(2) 0.0362(9) Uani 1 1 d . . . . .
H3 H 0.094931 0.271672 0.422118 0.043 Uiso 1 1 calc R U . . .
C4 C 0.0514(6) 0.3774(3) 0.3552(2) 0.0331(8) Uani 1 1 d . . . . .
H4 H -0.004545 0.344532 0.315481 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0781(5) 0.4720(2) 0.3507(2) 0.0284(8) Uani 1 1 d . . . . .
C6 C 0.1432(8) 0.5953(3) 0.2734(3) 0.0518(13) Uani 1 1 d . . . . .
H6A H 0.254886 0.572317 0.255111 0.062 Uiso 1 1 calc R U . . .
H6AB H 0.185566 0.628845 0.317098 0.062 Uiso 1 1 calc R U . . .
C7 C 0.0373(9) 0.6571(3) 0.2200(3) 0.0561(14) Uani 1 1 d . . . . .
H7A H -0.060904 0.687906 0.241620 0.067 Uiso 1 1 calc R U . . .
H7AB H 0.123689 0.703190 0.206666 0.067 Uiso 1 1 calc R U . . .
C8 C -0.1683(8) 0.5432(4) 0.1761(3) 0.0564(14) Uani 1 1 d . . . . .
H8A H -0.226402 0.512786 0.132771 0.068 Uiso 1 1 calc R U . . .
H8AB H -0.269186 0.570741 0.198409 0.068 Uiso 1 1 calc R U . . .
C9 C -0.0676(7) 0.4738(3) 0.2262(2) 0.0457(11) Uani 1 1 d . . . . .
H9A H -0.158224 0.429855 0.239632 0.055 Uiso 1 1 calc R U . . .
H9AB H 0.025307 0.441349 0.202838 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2889(5) 0.5354(2) 0.52795(19) 0.0271(7) Uani 1 1 d . . . . .
C11 C 0.3660(6) 0.5112(3) 0.5945(2) 0.0337(9) Uani 1 1 d . . . . .
H11 H 0.367801 0.450492 0.608883 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4435(6) 0.5795(3) 0.6416(2) 0.0363(9) Uani 1 1 d . . . . .
H12 H 0.501115 0.563377 0.687396 0.044 Uiso 1 1 calc R U . . .
C13 C 0.4369(6) 0.6675(3) 0.6225(2) 0.0338(9) Uani 1 1 d . . . . .
H13 H 0.490047 0.711603 0.654799 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3499(6) 0.6936(3) 0.5538(2) 0.0312(8) Uani 1 1 d . . . . .
C15 C 0.4485(7) 0.8526(3) 0.5588(3) 0.0437(11) Uani 1 1 d . . . . .
H15A H 0.543418 0.860391 0.527186 0.052 Uiso 1 1 calc R U . . .
H15B H 0.513617 0.837115 0.606099 0.052 Uiso 1 1 calc R U . . .
C16 C 0.3405(8) 0.9391(3) 0.5625(3) 0.0459(11) Uani 1 1 d . . . . .
H16A H 0.257528 0.933609 0.598859 0.055 Uiso 1 1 calc R U . . .
H16B H 0.428933 0.988555 0.576360 0.055 Uiso 1 1 calc R U . . .
C17 C 0.0956(6) 0.8912(3) 0.4780(3) 0.0401(10) Uani 1 1 d . . . . .
H17A H 0.013443 0.908219 0.434446 0.048 Uiso 1 1 calc R U . . .
H17B H 0.017531 0.884588 0.515874 0.048 Uiso 1 1 calc R U . . .
C18 C 0.1915(6) 0.8021(3) 0.4669(2) 0.0360(9) Uani 1 1 d . . . . .
H18A H 0.096898 0.754643 0.455830 0.043 Uiso 1 1 calc R U . . .
H18B H 0.263240 0.807287 0.427090 0.043 Uiso 1 1 calc R U . . .
P1 P 0.60056(17) 0.77028(8) 0.33394(6) 0.0377(3) Uani 1 1 d . . . . .
F1 F 0.6979(5) 0.8308(3) 0.2819(2) 0.0803(12) Uani 1 1 d . . . . .
F2 F 0.4020(5) 0.8139(3) 0.3057(2) 0.0816(12) Uani 1 1 d . . . . .
F3 F 0.5626(5) 0.6966(3) 0.27290(18) 0.0746(11) Uani 1 1 d . . . . .
F4 F 0.5007(5) 0.7062(2) 0.38503(16) 0.0542(8) Uani 1 1 d . . . . .
F5 F 0.7973(5) 0.7242(3) 0.36163(18) 0.0753(11) Uani 1 1 d . . . . .
F6 F 0.6370(8) 0.8416(3) 0.3951(2) 0.1017(16) 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
O1 C8 1.414(7) . ?
O1 C7 1.417(6) . ?
O2 C16 1.414(6) . ?
O2 C17 1.417(5) . ?
N1 C5 1.337(5) . ?
N1 C1 1.346(5) . ?
N2 C5 1.373(5) . ?
N2 C9 1.455(5) . ?
N2 C6 1.459(6) . ?
N3 C14 1.356(5) . ?
N3 C10 1.370(5) . ?
N3 H3N3 0.8700 . ?
N4 C14 1.338(5) . ?
N4 C18 1.475(5) . ?
N4 C15 1.475(5) . ?
C1 C2 1.384(5) . ?
C1 C10 1.486(5) . ?
C2 C3 1.393(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.377(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.420(5) . ?
C4 H4 0.9400 . ?
C6 C7 1.494(6) . ?
C6 H6A 0.9800 . ?
C6 H6AB 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7AB 0.9800 . ?
C8 C9 1.514(7) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C10 C11 1.357(5) . ?
C11 C12 1.413(6) . ?
C11 H11 0.9400 . ?
C12 C13 1.355(6) . ?
C12 H12 0.9400 . ?
C13 C14 1.420(5) . ?
C13 H13 0.9400 . ?
C15 C16 1.506(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.517(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
P1 F6 1.567(4) . ?
P1 F1 1.575(3) . ?
P1 F2 1.587(3) . ?
P1 F5 1.589(3) . ?
P1 F3 1.590(3) . ?
P1 F4 1.602(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
C8 O1 C7 109.9(4) . . ?
C16 O2 C17 109.9(3) . . ?
C5 N1 C1 118.8(3) . . ?
C5 N2 C9 120.0(3) . . ?
C5 N2 C6 118.5(3) . . ?
C9 N2 C6 113.6(4) . . ?
C14 N3 C10 125.4(3) . . ?
C14 N3 H3N3 117.3 . . ?
C10 N3 H3N3 117.3 . . ?
C14 N4 C18 122.3(3) . . ?
C14 N4 C15 121.7(3) . . ?
C18 N4 C15 113.6(3) . . ?
N1 C1 C2 124.3(3) . . ?
N1 C1 C10 113.7(3) . . ?
C2 C1 C10 121.9(3) . . ?
C1 C2 C3 116.6(4) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 N2 116.7(3) . . ?
N1 C5 C4 120.8(3) . . ?
N2 C5 C4 122.5(3) . . ?
N2 C6 C7 111.1(4) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6AB 109.4 . . ?
C7 C6 H6AB 109.4 . . ?
H6A C6 H6AB 108.0 . . ?
O1 C7 C6 113.1(4) . . ?
O1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
O1 C7 H7AB 109.0 . . ?
C6 C7 H7AB 109.0 . . ?
H7A C7 H7AB 107.8 . . ?
O1 C8 C9 112.8(4) . . ?
O1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
O1 C8 H8AB 109.0 . . ?
C9 C8 H8AB 109.0 . . ?
H8A C8 H8AB 107.8 . . ?
N2 C9 C8 108.9(4) . . ?
N2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N2 C9 H9AB 109.9 . . ?
C8 C9 H9AB 109.9 . . ?
H9A C9 H9AB 108.3 . . ?
C11 C10 N3 118.8(3) . . ?
C11 C10 C1 127.8(4) . . ?
N3 C10 C1 113.4(3) . . ?
C10 C11 C12 118.3(4) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
N4 C14 N3 119.6(3) . . ?
N4 C14 C13 124.9(4) . . ?
N3 C14 C13 115.5(4) . . ?
N4 C15 C16 110.1(4) . . ?
N4 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
O2 C16 C15 111.3(4) . . ?
O2 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
O2 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C17 C18 110.3(4) . . ?
O2 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O2 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N4 C18 C17 108.9(3) . . ?
N4 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
N4 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
F6 P1 F1 92.4(2) . . ?
F6 P1 F2 91.3(3) . . ?
F1 P1 F2 90.7(2) . . ?
F6 P1 F5 89.9(3) . . ?
F1 P1 F5 90.0(2) . . ?
F2 P1 F5 178.6(2) . . ?
F6 P1 F3 179.0(2) . . ?
F1 P1 F3 88.6(2) . . ?
F2 P1 F3 88.9(2) . . ?
F5 P1 F3 89.9(2) . . ?
F6 P1 F4 89.4(2) . . ?
F1 P1 F4 178.2(2) . . ?
F2 P1 F4 89.3(2) . . ?
F5 P1 F4 89.88(19) . . ?
F3 P1 F4 89.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.1(6) . . . . ?
C5 N1 C1 C10 -179.1(3) . . . . ?
N1 C1 C2 C3 0.9(6) . . . . ?
C10 C1 C2 C3 179.9(4) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
C1 N1 C5 N2 179.6(4) . . . . ?
C1 N1 C5 C4 0.0(6) . . . . ?
C9 N2 C5 N1 -177.0(4) . . . . ?
C6 N2 C5 N1 36.0(6) . . . . ?
C9 N2 C5 C4 2.6(6) . . . . ?
C6 N2 C5 C4 -144.4(4) . . . . ?
C3 C4 C5 N1 -0.8(6) . . . . ?
C3 C4 C5 N2 179.6(4) . . . . ?
C5 N2 C6 C7 -160.9(4) . . . . ?
C9 N2 C6 C7 50.1(6) . . . . ?
C8 O1 C7 C6 57.0(6) . . . . ?
N2 C6 C7 O1 -52.4(7) . . . . ?
C7 O1 C8 C9 -59.2(6) . . . . ?
C5 N2 C9 C8 160.4(4) . . . . ?
C6 N2 C9 C8 -51.1(6) . . . . ?
O1 C8 C9 N2 56.1(6) . . . . ?
C14 N3 C10 C11 -2.2(6) . . . . ?
C14 N3 C10 C1 179.3(4) . . . . ?
N1 C1 C10 C11 -175.0(4) . . . . ?
C2 C1 C10 C11 5.9(7) . . . . ?
N1 C1 C10 N3 3.3(5) . . . . ?
C2 C1 C10 N3 -175.8(4) . . . . ?
N3 C10 C11 C12 -1.2(6) . . . . ?
C1 C10 C11 C12 177.0(4) . . . . ?
C10 C11 C12 C13 2.1(7) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
C18 N4 C14 N3 10.3(7) . . . . ?
C15 N4 C14 N3 -151.1(4) . . . . ?
C18 N4 C14 C13 -165.8(4) . . . . ?
C15 N4 C14 C13 32.8(7) . . . . ?
C10 N3 C14 N4 -171.9(4) . . . . ?
C10 N3 C14 C13 4.5(6) . . . . ?
C12 C13 C14 N4 172.8(4) . . . . ?
C12 C13 C14 N3 -3.4(6) . . . . ?
C14 N4 C15 C16 -147.5(4) . . . . ?
C18 N4 C15 C16 49.6(6) . . . . ?
C17 O2 C16 C15 62.5(5) . . . . ?
N4 C15 C16 O2 -54.3(6) . . . . ?
C16 O2 C17 C18 -64.2(5) . . . . ?
C14 N4 C18 C17 146.2(4) . . . . ?
C15 N4 C18 C17 -51.1(5) . . . . ?
O2 C17 C18 N4 57.5(5) . . . . ?

_refine_diff_density_max         1.497
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.183

