# 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 2019

####################################################################### 
# 
# 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. 
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data_mo_NPK2_56_5_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1863988'
_audit_update_record             
;
2018-11-15 deposited with the CCDC.
2019-02-05 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         'C21 H21 N5'
_chemical_formula_sum            'C21 H21 N5'
_chemical_formula_weight         343.43

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                   12.2671(5)
_cell_length_b                   18.1570(8)
_cell_length_c                   15.9123(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.146(2)
_cell_angle_gamma                90
_cell_volume                     3523.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.72

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS,BRUKER
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54074
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         28.725
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4570
_reflns_number_gt                3435
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0713P)²+2.1996P] 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         4570
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_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 0.5711(3) 0.78950(17) 0.38707(19) 0.1071(11) Uani 1 1 d . . . . .
H1A H 0.5829 0.7382 0.3713 0.161 Uiso 1 1 calc R U . . .
H1B H 0.6347 0.8191 0.3757 0.161 Uiso 1 1 calc R U . . .
H1C H 0.5052 0.8086 0.3539 0.161 Uiso 1 1 calc R U . . .
C2 C 0.5566(2) 0.79358(15) 0.48094(16) 0.0858(8) Uani 1 1 d . . . . .
H2A H 0.6223 0.7728 0.5141 0.103 Uiso 1 1 calc R U . . .
H2B H 0.5501 0.8458 0.4975 0.103 Uiso 1 1 calc R U . . .
C3 C 0.45699(19) 0.75234(11) 0.50177(13) 0.0613(5) Uani 1 1 d . . . . .
H3A H 0.4612 0.7011 0.4810 0.074 Uiso 1 1 calc R U . . .
H3B H 0.3911 0.7754 0.4714 0.074 Uiso 1 1 calc R U . . .
C4 C 0.44379(16) 0.75054(10) 0.59636(12) 0.0532(5) Uani 1 1 d . . . . .
H4A H 0.4457 0.8016 0.6184 0.064 Uiso 1 1 calc R U . . .
H4B H 0.3713 0.7293 0.6044 0.064 Uiso 1 1 calc R U . . .
C5 C 0.53100(14) 0.70651(10) 0.64576(11) 0.0456(4) Uani 1 1 d . . . . .
C6 C 0.54773(12) 0.63132(9) 0.65349(9) 0.0368(3) Uani 1 1 d . . . . .
C7 C 0.69607(12) 0.55893(9) 0.72981(9) 0.0370(3) Uani 1 1 d . . . . .
C8 C 0.79594(13) 0.56035(11) 0.78017(10) 0.0461(4) Uani 1 1 d . . . . .
H8 H 0.8286 0.6060 0.7979 0.055 Uiso 1 1 calc R U . . .
C9 C 0.84704(13) 0.49512(11) 0.80415(11) 0.0481(4) Uani 1 1 d . . . . .
C10 C 0.79682(13) 0.42967(11) 0.77728(11) 0.0479(4) Uani 1 1 d . . . . .
H10 H 0.8326 0.3849 0.7944 0.057 Uiso 1 1 calc R U . . .
C11 C 0.69718(13) 0.42560(10) 0.72681(10) 0.0413(4) Uani 1 1 d . . . . .
C12 C 0.64522(11) 0.49284(9) 0.70278(9) 0.0347(3) Uani 1 1 d . . . . .
C13 C 0.40073(12) 0.46800(9) 0.57249(9) 0.0375(3) Uani 1 1 d . . . . .
C14 C 0.31575(13) 0.42783(11) 0.52476(11) 0.0474(4) Uani 1 1 d . . . . .
H14 H 0.3155 0.3755 0.5243 0.057 Uiso 1 1 calc R U . . .
C15 C 0.23513(14) 0.46705(12) 0.48001(11) 0.0524(5) Uani 1 1 d . . . . .
H15 H 0.1785 0.4414 0.4466 0.063 Uiso 1 1 calc R U . . .
C16 C 0.23278(13) 0.54426(12) 0.48152(11) 0.0524(5) Uani 1 1 d . . . . .
H16 H 0.1743 0.5694 0.4497 0.063 Uiso 1 1 calc R U . . .
C17 C 0.31248(13) 0.58406(11) 0.52753(11) 0.0458(4) Uani 1 1 d . . . . .
H17 H 0.3095 0.6363 0.5286 0.055 Uiso 1 1 calc R U . . .
C18 C 0.39986(11) 0.54555(9) 0.57364(9) 0.0354(3) Uani 1 1 d . . . . .
C19 C 0.49500(11) 0.56436(8) 0.62536(9) 0.0338(3) Uani 1 1 d . . . . .
C20 C 0.95507(16) 0.49450(15) 0.85952(14) 0.0675(6) Uani 1 1 d . . . . .
H20A H 0.9415 0.4893 0.9188 0.101 Uiso 1 1 calc R U . . .
H20B H 0.9941 0.5407 0.8521 0.101 Uiso 1 1 calc R U . . .
H20C H 0.9996 0.4530 0.8435 0.101 Uiso 1 1 calc R U . . .
C21 C 0.65365(17) 0.35077(11) 0.70269(14) 0.0595(5) Uani 1 1 d . . . . .
H21A H 0.7052 0.3132 0.7269 0.089 Uiso 1 1 calc R U . . .
H21B H 0.6447 0.3462 0.6410 0.089 Uiso 1 1 calc R U . . .
H21C H 0.5825 0.3439 0.7244 0.089 Uiso 1 1 calc R U . . .
N1 N 0.61610(14) 0.74059(9) 0.69205(11) 0.0560(4) Uani 1 1 d . . . . .
N2 N 0.68477(12) 0.69186(9) 0.72828(10) 0.0537(4) Uani 1 1 d . . . . .
N3 N 0.64376(10) 0.62508(8) 0.70498(8) 0.0399(3) Uani 1 1 d . . . . .
N4 N 0.54438(9) 0.49867(7) 0.65045(8) 0.0333(3) Uani 1 1 d . . . . .
N5 N 0.48794(10) 0.43887(7) 0.61912(8) 0.0399(3) 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 1.525(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.500(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.491(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.360(2) . ?
C5 C6 1.384(2) . ?
C6 N3 1.3657(19) . ?
C6 C19 1.427(2) . ?
C7 C8 1.391(2) . ?
C7 C12 1.399(2) . ?
C7 N3 1.399(2) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 C20 1.511(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(2) . ?
C11 C21 1.495(3) . ?
C12 N4 1.4191(18) . ?
C13 N5 1.343(2) . ?
C13 C18 1.408(2) . ?
C13 C14 1.423(2) . ?
C14 C15 1.357(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.364(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.417(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.397(2) . ?
C19 N4 1.3773(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 N2 1.312(2) . ?
N2 N3 1.349(2) . ?
N4 N5 1.3539(17) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 112.1(2) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 113.72(19) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 112.60(16) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C6 107.62(15) . . ?
N1 C5 C4 120.50(16) . . ?
C6 C5 C4 131.85(16) . . ?
N3 C6 C5 104.20(14) . . ?
N3 C6 C19 116.78(14) . . ?
C5 C6 C19 139.01(14) . . ?
C8 C7 C12 121.98(16) . . ?
C8 C7 N3 119.74(15) . . ?
C12 C7 N3 118.29(13) . . ?
C9 C8 C7 119.43(17) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.62(15) . . ?
C8 C9 C20 120.91(18) . . ?
C10 C9 C20 120.47(18) . . ?
C9 C10 C11 123.93(17) . . ?
C9 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C12 117.01(16) . . ?
C10 C11 C21 117.66(16) . . ?
C12 C11 C21 125.33(15) . . ?
C7 C12 C11 119.03(14) . . ?
C7 C12 N4 116.64(13) . . ?
C11 C12 N4 124.31(14) . . ?
N5 C13 C18 113.15(13) . . ?
N5 C13 C14 125.98(16) . . ?
C18 C13 C14 120.88(14) . . ?
C15 C14 C13 117.51(17) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 C16 122.06(16) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 121.60(16) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 118.38(18) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C13 104.19(13) . . ?
C19 C18 C17 136.27(16) . . ?
C13 C18 C17 119.54(14) . . ?
N4 C19 C18 105.84(13) . . ?
N4 C19 C6 118.45(13) . . ?
C18 C19 C6 135.69(14) . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 N1 C5 110.53(15) . . ?
N1 N2 N3 106.40(14) . . ?
N2 N3 C6 111.26(14) . . ?
N2 N3 C7 123.22(13) . . ?
C6 N3 C7 125.51(13) . . ?
N5 N4 C19 113.32(12) . . ?
N5 N4 C12 122.38(12) . . ?
C19 N4 C12 124.29(13) . . ?
C13 N5 N4 103.50(13) . . ?

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
C1 C2 C3 C4 176.0(2) . . . . ?
C2 C3 C4 C5 -67.3(2) . . . . ?
C3 C4 C5 N1 102.5(2) . . . . ?
C3 C4 C5 C6 -75.0(3) . . . . ?
N1 C5 C6 N3 0.00(18) . . . . ?
C4 C5 C6 N3 177.69(18) . . . . ?
N1 C5 C6 C19 178.89(18) . . . . ?
C4 C5 C6 C19 -3.4(4) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
N3 C7 C8 C9 -179.82(14) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C20 -179.42(16) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C20 C9 C10 C11 179.54(17) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C21 179.75(17) . . . . ?
C8 C7 C12 C11 -0.5(2) . . . . ?
N3 C7 C12 C11 179.61(13) . . . . ?
C8 C7 C12 N4 -178.97(14) . . . . ?
N3 C7 C12 N4 1.1(2) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C21 C11 C12 C7 -179.68(16) . . . . ?
C10 C11 C12 N4 178.93(14) . . . . ?
C21 C11 C12 N4 -1.3(3) . . . . ?
N5 C13 C14 C15 -178.67(16) . . . . ?
C18 C13 C14 C15 0.7(2) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
N5 C13 C18 C19 0.12(17) . . . . ?
C14 C13 C18 C19 -179.33(14) . . . . ?
N5 C13 C18 C17 -179.73(14) . . . . ?
C14 C13 C18 C17 0.8(2) . . . . ?
C16 C17 C18 C19 178.64(17) . . . . ?
C16 C17 C18 C13 -1.6(2) . . . . ?
C13 C18 C19 N4 0.10(16) . . . . ?
C17 C18 C19 N4 179.92(17) . . . . ?
C13 C18 C19 C6 178.65(17) . . . . ?
C17 C18 C19 C6 -1.5(3) . . . . ?
N3 C6 C19 N4 -1.0(2) . . . . ?
C5 C6 C19 N4 -179.77(18) . . . . ?
N3 C6 C19 C18 -179.39(16) . . . . ?
C5 C6 C19 C18 1.8(3) . . . . ?
C6 C5 N1 N2 -0.1(2) . . . . ?
C4 C5 N1 N2 -178.10(17) . . . . ?
C5 N1 N2 N3 0.2(2) . . . . ?
N1 N2 N3 C6 -0.16(19) . . . . ?
N1 N2 N3 C7 178.48(14) . . . . ?
C5 C6 N3 N2 0.09(18) . . . . ?
C19 C6 N3 N2 -179.09(13) . . . . ?
C5 C6 N3 C7 -178.51(14) . . . . ?
C19 C6 N3 C7 2.3(2) . . . . ?
C8 C7 N3 N2 -0.8(2) . . . . ?
C12 C7 N3 N2 179.15(14) . . . . ?
C8 C7 N3 C6 177.67(15) . . . . ?
C12 C7 N3 C6 -2.4(2) . . . . ?
C18 C19 N4 N5 -0.30(17) . . . . ?
C6 C19 N4 N5 -179.15(13) . . . . ?
C18 C19 N4 C12 178.73(13) . . . . ?
C6 C19 N4 C12 -0.1(2) . . . . ?
C7 C12 N4 N5 178.99(13) . . . . ?
C11 C12 N4 N5 0.6(2) . . . . ?
C7 C12 N4 C19 0.0(2) . . . . ?
C11 C12 N4 C19 -178.37(14) . . . . ?
C18 C13 N5 N4 -0.29(17) . . . . ?
C14 C13 N5 N4 179.13(15) . . . . ?
C19 N4 N5 C13 0.36(17) . . . . ?
C12 N4 N5 C13 -178.69(13) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.050

