# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 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_TPR12
_database_code_depnum_ccdc_archive 'CCDC 1950536'
loop_
_audit_author_name
_audit_author_address
'senthilnathan natarajan'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2020-04-23 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         'C22 H32 N4'
_chemical_formula_sum            'C22 H32 N4'
_chemical_formula_weight         352.51

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.9834(4)
_cell_length_b                   18.5034(6)
_cell_length_c                   20.9250(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.465(3)
_cell_angle_gamma                90
_cell_volume                     4530.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11251
_cell_measurement_theta_min      1.9870
_cell_measurement_theta_max      26.8020

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.034
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18934
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.059
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3965
_reflns_number_gt                3058
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1575P)²+7.8551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3965
_refine_ls_number_parameters     268
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0878
_refine_ls_wR_factor_ref         0.2723
_refine_ls_wR_factor_gt          0.2542
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.051
_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 0.7878(2) 0.60992(14) 0.46614(12) 0.0365(6) Uani 1 1 d . . . . .
C2 C 0.7243(2) 0.64887(15) 0.50412(13) 0.0385(7) Uani 1 1 d . . . . .
H2 H 0.673297 0.685647 0.484041 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7350(2) 0.63457(15) 0.56988(13) 0.0399(7) Uani 1 1 d . . . . .
H3 H 0.692441 0.662126 0.594636 0.048 Uiso 1 1 calc R U . . .
C4 C 0.8078(2) 0.57999(15) 0.60032(13) 0.0380(7) Uani 1 1 d . . . . .
C5 C 0.8700(2) 0.54023(15) 0.56286(13) 0.0397(7) Uani 1 1 d . . . . .
H5 H 0.919371 0.502646 0.582864 0.048 Uiso 1 1 calc R U . . .
C6 C 0.8603(2) 0.55493(15) 0.49755(13) 0.0395(7) Uani 1 1 d . . . . .
H6 H 0.903544 0.527413 0.473141 0.047 Uiso 1 1 calc R U . . .
C7 C 0.7792(3) 0.62609(15) 0.39767(13) 0.0399(7) Uani 1 1 d . . . . .
C8 C 0.8441(3) 0.58790(15) 0.36051(12) 0.0419(7) Uani 1 1 d . . . . .
C9 C 0.7077(3) 0.68113(16) 0.36549(13) 0.0441(7) Uani 1 1 d . . . . .
C10 C 0.8259(2) 0.56761(15) 0.67167(13) 0.0382(7) Uani 1 1 d . . . . .
C11 C 0.7759(9) 0.4357(4) 0.6619(4) 0.0406(18) Uani 0.562(10) 1 d D U P A 1
H11A H 0.832583 0.395997 0.669329 0.049 Uiso 0.562(10) 1 calc R U P A 1
H11B H 0.755439 0.445265 0.614210 0.049 Uiso 0.562(10) 1 calc R U P A 1
C12 C 0.6696(7) 0.4113(4) 0.6844(3) 0.0550(17) Uani 0.562(10) 1 d D U P A 1
H12A H 0.688932 0.403911 0.732336 0.066 Uiso 0.562(10) 1 calc R U P A 1
H12B H 0.643842 0.364436 0.663555 0.066 Uiso 0.562(10) 1 calc R U P A 1
C13 C 0.5727(7) 0.4657(5) 0.6674(4) 0.075(2) Uani 0.562(10) 1 d D U P A 1
H13A H 0.510502 0.450109 0.688684 0.090 Uiso 0.562(10) 1 calc R U P A 1
H13B H 0.600844 0.512958 0.686596 0.090 Uiso 0.562(10) 1 calc R U P A 1
C14 C 0.5278(6) 0.4754(4) 0.6023(4) 0.073(2) Uani 0.562(10) 1 d D U P A 1
H14A H 0.499674 0.428639 0.582110 0.087 Uiso 0.562(10) 1 calc R U P A 1
H14B H 0.588073 0.493265 0.580466 0.087 Uiso 0.562(10) 1 calc R U P A 1
C15 C 0.4283(8) 0.5304(5) 0.5920(6) 0.104(3) Uani 0.562(10) 1 d D U P A 1
H15A H 0.362686 0.508434 0.606607 0.125 Uiso 0.562(10) 1 calc R U P A 1
H15B H 0.452675 0.573528 0.619474 0.125 Uiso 0.562(10) 1 calc R U P A 1
C16 C 0.3907(8) 0.5534(5) 0.5221(6) 0.110(3) Uani 0.562(10) 1 d D U P A 1
H16A H 0.327765 0.588074 0.518092 0.165 Uiso 0.562(10) 1 calc R U P A 1
H16B H 0.454891 0.576146 0.507642 0.165 Uiso 0.562(10) 1 calc R U P A 1
H16C H 0.364896 0.511048 0.494774 0.165 Uiso 0.562(10) 1 calc R U P A 1
C11' C 0.8058(10) 0.4341(8) 0.6607(8) 0.046(3) Uiso 0.438(10) 1 d D U P A 2
H11C H 0.876229 0.404557 0.667131 0.055 Uiso 0.438(10) 1 calc R U P A 2
H11D H 0.779740 0.443770 0.613242 0.055 Uiso 0.438(10) 1 calc R U P A 2
C12' C 0.7134(9) 0.3928(6) 0.6855(5) 0.061(3) Uiso 0.438(10) 1 d D U P A 2
H12C H 0.689478 0.351340 0.655751 0.073 Uiso 0.438(10) 1 calc R U P A 2
H12D H 0.748408 0.372712 0.729044 0.073 Uiso 0.438(10) 1 calc R U P A 2
C13' C 0.6079(12) 0.4336(8) 0.6916(6) 0.083(3) Uiso 0.438(10) 1 d D U P A 2
H13C H 0.638331 0.471232 0.724290 0.100 Uiso 0.438(10) 1 calc R U P A 2
H13D H 0.568088 0.398885 0.714995 0.100 Uiso 0.438(10) 1 calc R U P A 2
C14' C 0.5082(17) 0.4726(11) 0.6458(11) 0.151(6) Uiso 0.438(10) 1 d D U P A 2
H14C H 0.544693 0.490525 0.610656 0.182 Uiso 0.438(10) 1 calc R U P A 2
H14D H 0.459552 0.431796 0.625813 0.182 Uiso 0.438(10) 1 calc R U P A 2
C15' C 0.4236(16) 0.5292(10) 0.6488(9) 0.144(6) Uiso 0.438(10) 1 d D U P A 2
H15C H 0.457624 0.566240 0.681300 0.173 Uiso 0.438(10) 1 calc R U P A 2
H15D H 0.356915 0.507857 0.662708 0.173 Uiso 0.438(10) 1 calc R U P A 2
C16' C 0.3858(16) 0.5635(10) 0.5830(8) 0.127(6) Uiso 0.438(10) 1 d D U P A 2
H16D H 0.329334 0.601183 0.585271 0.191 Uiso 0.438(10) 1 calc R U P A 2
H16E H 0.451866 0.585009 0.569597 0.191 Uiso 0.438(10) 1 calc R U P A 2
H16F H 0.351373 0.526752 0.551045 0.191 Uiso 0.438(10) 1 calc R U P A 2
C17 C 0.8576(3) 0.61854(17) 0.78226(14) 0.0493(8) Uani 1 1 d . . . . .
H17A H 0.926833 0.589252 0.799067 0.059 Uiso 1 1 calc R U . . .
H17B H 0.791644 0.592564 0.792844 0.059 Uiso 1 1 calc R U . . .
C18 C 0.8701(3) 0.68962(19) 0.81683(16) 0.0586(9) Uani 1 1 d . . . . .
H18A H 0.796186 0.715605 0.806914 0.070 Uiso 1 1 calc R U . . .
H18B H 0.927206 0.719477 0.801025 0.070 Uiso 1 1 calc R U . . .
C19 C 0.9083(5) 0.6787(2) 0.8909(2) 0.0795(13) Uani 1 1 d . . . . .
H19A H 0.856872 0.642822 0.904649 0.095 Uiso 1 1 calc R U . . .
H19B H 0.986115 0.657653 0.900193 0.095 Uiso 1 1 calc R U . . .
C20 C 0.9102(4) 0.7441(2) 0.93200(19) 0.0736(11) Uani 1 1 d . . . . .
H20A H 0.830996 0.762364 0.926270 0.088 Uiso 1 1 calc R U . . .
H20B H 0.955321 0.781850 0.915443 0.088 Uiso 1 1 calc R U . . .
C21 C 0.9595(4) 0.7341(2) 1.0055(2) 0.0762(11) Uani 1 1 d . . . . .
H21A H 1.041068 0.720333 1.012368 0.091 Uiso 1 1 calc R U . . .
H21B H 0.954970 0.780495 1.028404 0.091 Uiso 1 1 calc R U . . .
C22 C 0.8976(4) 0.6787(2) 1.0331(2) 0.0804(12) Uani 1 1 d . . . . .
H22A H 0.930930 0.673549 1.079930 0.121 Uiso 1 1 calc R U . . .
H22B H 0.817140 0.692716 1.026965 0.121 Uiso 1 1 calc R U . . .
H22C H 0.903159 0.632609 1.010944 0.121 Uiso 1 1 calc R U . . .
N1 N 0.8407(2) 0.62419(14) 0.71067(11) 0.0425(6) Uani 1 1 d . . . . .
N2 N 0.8298(2) 0.50172(14) 0.69580(14) 0.0438(7) Uani 1 1 d . . . . .
N3 N 0.6499(3) 0.72696(14) 0.33904(12) 0.0569(8) Uani 1 1 d . . . . .
N4 N 0.8984(2) 0.55595(14) 0.33051(11) 0.0511(7) Uani 1 1 d . . . . .
H10B H 0.847(3) 0.5002(18) 0.7282(18) 0.032(9) Uiso 1 1 d . . . . .
H10A H 0.852(3) 0.665(2) 0.696(2) 0.060(11) Uiso 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 C6 1.406(4) . ?
C1 C2 1.411(4) . ?
C1 C7 1.445(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.395(4) . ?
C4 C5 1.401(4) . ?
C4 C10 1.479(4) . ?
C5 C6 1.373(4) . ?
C7 C8 1.403(4) . ?
C7 C9 1.406(4) . ?
C8 N4 1.160(4) . ?
C9 N3 1.157(4) . ?
C10 N1 1.316(4) . ?
C10 N2 1.317(4) . ?
C11 N2 1.487(10) . ?
C11 C12 1.519(10) . ?
C12 C13 1.519(11) . ?
C13 C14 1.366(11) . ?
C14 C15 1.547(11) . ?
C15 C16 1.496(13) . ?
C11' N2 1.449(16) . ?
C11' C12' 1.525(11) . ?
C12' C13' 1.502(13) . ?
C13' C14' 1.540(16) . ?
C14' C15' 1.468(16) . ?
C15' C16' 1.494(16) . ?
C17 N1 1.471(4) . ?
C17 C18 1.493(5) . ?
C18 C19 1.533(5) . ?
C19 C20 1.482(6) . ?
C20 C21 1.535(6) . ?
C21 C22 1.456(6) . ?

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
C6 C1 C2 117.4(2) . . ?
C6 C1 C7 121.2(2) . . ?
C2 C1 C7 121.4(2) . . ?
C3 C2 C1 121.2(2) . . ?
C2 C3 C4 120.6(2) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 C10 120.9(2) . . ?
C5 C4 C10 120.2(2) . . ?
C6 C5 C4 120.8(2) . . ?
C5 C6 C1 121.3(2) . . ?
C8 C7 C9 116.9(2) . . ?
C8 C7 C1 121.1(2) . . ?
C9 C7 C1 122.0(2) . . ?
N4 C8 C7 179.1(3) . . ?
N3 C9 C7 179.2(4) . . ?
N1 C10 N2 120.7(2) . . ?
N1 C10 C4 118.3(2) . . ?
N2 C10 C4 121.0(3) . . ?
N2 C11 C12 113.7(6) . . ?
C11 C12 C13 112.4(6) . . ?
C14 C13 C12 115.9(6) . . ?
C13 C14 C15 110.5(8) . . ?
C16 C15 C14 112.5(9) . . ?
N2 C11' C12' 109.8(10) . . ?
C13' C12' C11' 117.6(10) . . ?
C12' C13' C14' 137.5(13) . . ?
C15' C14' C13' 139.3(18) . . ?
C14' C15' C16' 109.8(17) . . ?
N1 C17 C18 114.1(3) . . ?
C17 C18 C19 110.6(3) . . ?
C20 C19 C18 116.3(3) . . ?
C19 C20 C21 115.9(4) . . ?
C22 C21 C20 111.3(4) . . ?
C10 N1 C17 123.1(3) . . ?
C10 N2 C11' 128.2(6) . . ?
C10 N2 C11 127.0(4) . . ?

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.065



