# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2310051'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N5'
_chemical_formula_sum            'C15 H19 N5'
_chemical_formula_weight         269.35

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

_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                   8.86700(10)
_cell_length_b                   7.14300(10)
_cell_length_c                   22.2918(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.5370(10)
_cell_angle_gamma                90
_cell_volume                     1411.83(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12313
_cell_measurement_theta_min      3.9540
_cell_measurement_theta_max      76.3320

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.631
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            19004
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.966
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_full        67.076
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2524
_reflns_number_gt                2371
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'
_refine_special_details          
;
Owing to poor agreement, one reflection, i.e. (-1 1 16), was omitted from the
final cycles of refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.5720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     188
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.006
_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 0.06777(10) 0.68711(13) 0.33098(4) 0.0146(2) Uani 1 1 d . . . . .
N3 N 0.17071(10) 0.38980(13) 0.30229(4) 0.0142(2) Uani 1 1 d . . . . .
N5 N 0.27928(10) 0.56361(14) 0.38401(4) 0.0147(2) Uani 1 1 d . . . . .
N21 N -0.03617(11) 0.51613(14) 0.25403(4) 0.0163(2) Uani 1 1 d D . . . .
H1N H -0.0895(15) 0.6168(16) 0.2449(6) 0.020 Uiso 1 1 d D U . . .
H2N H -0.0303(16) 0.4236(17) 0.2281(5) 0.020 Uiso 1 1 d D U . . .
N41 N 0.39312(11) 0.29576(14) 0.34900(4) 0.0167(2) Uani 1 1 d . . . . .
C2 C 0.07079(12) 0.53013(16) 0.29694(5) 0.0134(2) Uani 1 1 d . . . . .
C4 C 0.27738(12) 0.41784(16) 0.34504(5) 0.0136(2) Uani 1 1 d . . . . .
C6 C 0.17304(12) 0.69170(16) 0.37445(5) 0.0133(2) Uani 1 1 d . . . . .
C42 C 0.40882(13) 0.13428(17) 0.30913(6) 0.0195(3) Uani 1 1 d . . . . .
H42A H 0.331824 0.141434 0.276765 0.023 Uiso 1 1 calc R U . . .
H42B H 0.391372 0.017706 0.332066 0.023 Uiso 1 1 calc R U . . .
C43 C 0.56532(13) 0.12868(18) 0.28166(5) 0.0202(3) Uani 1 1 d . . . . .
H43A H 0.576826 0.235772 0.253883 0.024 Uiso 1 1 calc R U . . .
H43B H 0.576492 0.011957 0.258170 0.024 Uiso 1 1 calc R U . . .
C44 C 0.68866(14) 0.1373(2) 0.32975(6) 0.0250(3) Uani 1 1 d . . . . .
H44A H 0.686200 0.021858 0.354307 0.030 Uiso 1 1 calc R U . . .
H44B H 0.788583 0.145045 0.310463 0.030 Uiso 1 1 calc R U . . .
C45 C 0.66570(13) 0.30727(19) 0.36987(6) 0.0229(3) Uani 1 1 d . . . . .
H45A H 0.741532 0.305767 0.402751 0.028 Uiso 1 1 calc R U . . .
H45B H 0.680820 0.422897 0.346191 0.028 Uiso 1 1 calc R U . . .
C46 C 0.50828(13) 0.30824(17) 0.39633(5) 0.0183(3) Uani 1 1 d . . . . .
H46A H 0.497550 0.201019 0.424109 0.022 Uiso 1 1 calc R U . . .
H46B H 0.493505 0.424837 0.419553 0.022 Uiso 1 1 calc R U . . .
C61 C 0.17381(12) 0.85698(16) 0.41513(5) 0.0142(3) Uani 1 1 d . . . . .
C62 C 0.28159(13) 0.87179(16) 0.46108(5) 0.0166(3) Uani 1 1 d . . . . .
H62 H 0.352393 0.773733 0.467334 0.020 Uiso 1 1 calc R U . . .
C63 C 0.28559(13) 1.02892(17) 0.49755(5) 0.0181(3) Uani 1 1 d . . . . .
H63 H 0.359061 1.036409 0.528745 0.022 Uiso 1 1 calc R U . . .
C64 C 0.18442(13) 1.17598(16) 0.48950(5) 0.0169(3) Uani 1 1 d . . . . .
C65 C 0.07632(13) 1.15947(17) 0.44396(5) 0.0177(3) Uani 1 1 d . . . . .
H65 H 0.005691 1.257752 0.437771 0.021 Uiso 1 1 calc R U . . .
C66 C 0.07008(13) 1.00242(16) 0.40761(5) 0.0161(3) Uani 1 1 d . . . . .
H66 H -0.005493 0.993511 0.377255 0.019 Uiso 1 1 calc R U . . .
C67 C 0.19316(14) 1.34785(17) 0.52839(6) 0.0221(3) Uani 1 1 d . . . . .
H67A H 0.285112 1.343083 0.553079 0.033 Uiso 1 1 calc R U . . .
H67B H 0.104862 1.352671 0.554463 0.033 Uiso 1 1 calc R U . . .
H67C H 0.195186 1.459736 0.502972 0.033 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 C6 1.3396(15) . ?
N1 C2 1.3543(15) . ?
N3 C2 1.3424(15) . ?
N3 C4 1.3513(15) . ?
N5 C6 1.3289(15) . ?
N5 C4 1.3560(15) . ?
N21 C2 1.3443(15) . ?
N21 H1N 0.883(9) . ?
N21 H2N 0.880(9) . ?
N41 C4 1.3490(15) . ?
N41 C42 1.4636(15) . ?
N41 C46 1.4641(14) . ?
C6 C61 1.4887(16) . ?
C42 C43 1.5226(16) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.5256(17) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.5228(17) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.5204(17) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C61 C66 1.3965(16) . ?
C61 C62 1.3984(16) . ?
C62 C63 1.3860(17) . ?
C62 H62 0.9500 . ?
C63 C64 1.3919(17) . ?
C63 H63 0.9500 . ?
C64 C65 1.3945(17) . ?
C64 C67 1.5045(16) . ?
C65 C66 1.3847(17) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 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
C6 N1 C2 114.09(9) . . ?
C2 N3 C4 114.14(10) . . ?
C6 N5 C4 114.92(10) . . ?
C2 N21 H1N 118.4(9) . . ?
C2 N21 H2N 118.5(9) . . ?
H1N N21 H2N 119.7(13) . . ?
C4 N41 C42 123.11(10) . . ?
C4 N41 C46 122.20(9) . . ?
C42 N41 C46 114.58(9) . . ?
N3 C2 N21 117.92(10) . . ?
N3 C2 N1 125.80(10) . . ?
N21 C2 N1 116.27(10) . . ?
N41 C4 N3 118.52(10) . . ?
N41 C4 N5 116.71(10) . . ?
N3 C4 N5 124.75(10) . . ?
N5 C6 N1 125.96(10) . . ?
N5 C6 C61 116.69(10) . . ?
N1 C6 C61 117.34(10) . . ?
N41 C42 C43 110.93(10) . . ?
N41 C42 H42A 109.5 . . ?
C43 C42 H42A 109.5 . . ?
N41 C42 H42B 109.5 . . ?
C43 C42 H42B 109.5 . . ?
H42A C42 H42B 108.0 . . ?
C42 C43 C44 111.49(10) . . ?
C42 C43 H43A 109.3 . . ?
C44 C43 H43A 109.3 . . ?
C42 C43 H43B 109.3 . . ?
C44 C43 H43B 109.3 . . ?
H43A C43 H43B 108.0 . . ?
C45 C44 C43 110.24(10) . . ?
C45 C44 H44A 109.6 . . ?
C43 C44 H44A 109.6 . . ?
C45 C44 H44B 109.6 . . ?
C43 C44 H44B 109.6 . . ?
H44A C44 H44B 108.1 . . ?
C46 C45 C44 111.08(10) . . ?
C46 C45 H45A 109.4 . . ?
C44 C45 H45A 109.4 . . ?
C46 C45 H45B 109.4 . . ?
C44 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
N41 C46 C45 110.90(9) . . ?
N41 C46 H46A 109.5 . . ?
C45 C46 H46A 109.5 . . ?
N41 C46 H46B 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 108.0 . . ?
C66 C61 C62 118.46(10) . . ?
C66 C61 C6 121.16(10) . . ?
C62 C61 C6 120.36(10) . . ?
C63 C62 C61 120.29(11) . . ?
C63 C62 H62 119.9 . . ?
C61 C62 H62 119.9 . . ?
C62 C63 C64 121.51(11) . . ?
C62 C63 H63 119.2 . . ?
C64 C63 H63 119.2 . . ?
C63 C64 C65 117.89(10) . . ?
C63 C64 C67 120.79(11) . . ?
C65 C64 C67 121.32(11) . . ?
C66 C65 C64 121.19(11) . . ?
C66 C65 H65 119.4 . . ?
C64 C65 H65 119.4 . . ?
C65 C66 C61 120.64(11) . . ?
C65 C66 H66 119.7 . . ?
C61 C66 H66 119.7 . . ?
C64 C67 H67A 109.5 . . ?
C64 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C64 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 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
C4 N3 C2 N21 177.83(9) . . . . ?
C4 N3 C2 N1 -1.88(16) . . . . ?
C6 N1 C2 N3 -2.54(15) . . . . ?
C6 N1 C2 N21 177.75(9) . . . . ?
C42 N41 C4 N3 0.06(16) . . . . ?
C46 N41 C4 N3 -175.94(10) . . . . ?
C42 N41 C4 N5 -178.44(10) . . . . ?
C46 N41 C4 N5 5.56(16) . . . . ?
C2 N3 C4 N41 -172.16(9) . . . . ?
C2 N3 C4 N5 6.20(16) . . . . ?
C6 N5 C4 N41 172.85(9) . . . . ?
C6 N5 C4 N3 -5.54(16) . . . . ?
C4 N5 C6 N1 0.33(16) . . . . ?
C4 N5 C6 C61 -178.28(9) . . . . ?
C2 N1 C6 N5 3.38(16) . . . . ?
C2 N1 C6 C61 -178.01(9) . . . . ?
C4 N41 C42 C43 128.89(11) . . . . ?
C46 N41 C42 C43 -54.83(13) . . . . ?
N41 C42 C43 C44 53.44(13) . . . . ?
C42 C43 C44 C45 -54.15(14) . . . . ?
C43 C44 C45 C46 54.66(14) . . . . ?
C4 N41 C46 C45 -128.12(11) . . . . ?
C42 N41 C46 C45 55.56(13) . . . . ?
C44 C45 C46 N41 -54.68(14) . . . . ?
N5 C6 C61 C66 177.86(10) . . . . ?
N1 C6 C61 C66 -0.88(15) . . . . ?
N5 C6 C61 C62 -0.58(15) . . . . ?
N1 C6 C61 C62 -179.32(9) . . . . ?
C66 C61 C62 C63 -0.82(17) . . . . ?
C6 C61 C62 C63 177.66(10) . . . . ?
C61 C62 C63 C64 -0.45(18) . . . . ?
C62 C63 C64 C65 1.04(17) . . . . ?
C62 C63 C64 C67 -178.28(11) . . . . ?
C63 C64 C65 C66 -0.36(17) . . . . ?
C67 C64 C65 C66 178.95(11) . . . . ?
C64 C65 C66 C61 -0.91(17) . . . . ?
C62 C61 C66 C65 1.50(17) . . . . ?
C6 C61 C66 C65 -176.97(10) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.049



