# 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 2022

####################################################################### 
# 
# 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_MKB_PM_16_XRD_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2087550'
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2022-05-02 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            'C H N'
_chemical_formula_weight         27.03

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.036(18)
_cell_length_b                   10.55(2)
_cell_length_c                   13.26(3)
_cell_angle_alpha                93.56(5)
_cell_angle_beta                 96.81(4)
_cell_angle_gamma                94.96(5)
_cell_volume                     1109(4)
_cell_formula_units_Z            33
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2613
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      25.1

_exptl_crystal_description       Needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.094
_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      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26748
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_av_R_equivalents  0.12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.396
_diffrn_reflns_theta_max         25.213
_diffrn_reflns_theta_full        25.213
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3989
_reflns_number_gt                3031
_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)+(0.2000P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       1.7
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3989
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2891
_refine_ls_wR_factor_gt          0.2450
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.007

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 0.7611(2) 0.62406(17) 0.56558(13) 0.0441(5) Uani 1 1 d . . . . .
N2 N 0.6790(2) 0.57107(17) 0.38905(13) 0.0446(5) Uani 1 1 d . . . . .
C20 C 0.7337(3) 0.5428(2) 0.48336(15) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.4592(3) 0.6843(2) 0.09884(16) 0.0398(6) Uani 1 1 d . . . . .
C28 C 0.7735(3) 0.4109(2) 0.49558(16) 0.0444(6) Uani 1 1 d . . . . .
C12 C 0.4855(3) 0.6489(2) 0.20004(16) 0.0384(6) Uani 1 1 d . . . . .
C19 C 0.7256(3) 0.7433(2) 0.55294(16) 0.0433(6) Uani 1 1 d . . . . .
C3 C 0.5994(3) 0.7263(2) 0.27156(16) 0.0420(6) Uani 1 1 d . . . . .
C21 C 0.7620(3) 0.8339(2) 0.64372(17) 0.0433(6) Uani 1 1 d . . . . .
C17 C 0.6453(3) 0.6917(2) 0.37710(17) 0.0424(6) Uani 1 1 d . . . . .
C16 C 0.3486(3) 0.6063(2) 0.02425(17) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.5440(3) 0.7962(2) 0.06979(18) 0.0442(6) Uani 1 1 d . . . . .
C14 C 0.3236(3) 0.6408(2) -0.07754(16) 0.0502(7) Uani 1 1 d . . . . .
C4 C 0.3924(3) 0.5366(2) 0.22570(17) 0.0466(6) Uani 1 1 d . . . . .
H4 H 0.4044 0.5138 0.2926 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2640(3) 0.4939(2) 0.05144(17) 0.0446(6) Uani 1 1 d . . . . .
C18 C 0.6644(3) 0.7801(2) 0.45874(16) 0.0471(6) Uani 1 1 d . . . . .
H18 H 0.6368 0.8630 0.4508 0.056 Uiso 1 1 calc R U . . .
C26 C 0.8901(3) 0.8157(2) 0.71928(17) 0.0489(6) Uani 1 1 d . . . . .
H26 H 0.9493 0.7442 0.7140 0.059 Uiso 1 1 calc R U . . .
C1 C 0.6528(3) 0.8720(2) 0.14321(18) 0.0498(6) Uani 1 1 d . . . . .
H1 H 0.7079 0.9472 0.1258 0.060 Uiso 1 1 calc R U . . .
C2 C 0.6792(3) 0.8364(2) 0.24137(18) 0.0483(6) Uani 1 1 d . . . . .
H2 H 0.7532 0.8882 0.2891 0.058 Uiso 1 1 calc R U . . .
C24 C 0.8453(3) 1.0086(2) 0.81270(18) 0.0525(7) Uani 1 1 d . . . . .
C10 C 0.5154(4) 0.8271(2) -0.03432(19) 0.0556(7) Uani 1 1 d . . . . .
H10 H 0.5713 0.9006 -0.0540 0.067 Uiso 1 1 calc R U . . .
C33 C 0.8673(3) 0.3796(2) 0.58345(18) 0.0525(7) Uani 1 1 d . . . . .
H33 H 0.9033 0.4419 0.6361 0.063 Uiso 1 1 calc R U . . .
C5 C 0.2876(3) 0.4634(2) 0.15431(18) 0.0491(6) Uani 1 1 d . . . . .
H5 H 0.2289 0.3905 0.1731 0.059 Uiso 1 1 calc R U . . .
C22 C 0.6754(3) 0.9397(2) 0.65542(19) 0.0550(7) Uani 1 1 d . . . . .
H22 H 0.5877 0.9535 0.6061 0.066 Uiso 1 1 calc R U . . .
C25 C 0.9303(3) 0.9022(2) 0.80173(19) 0.0557(7) Uani 1 1 d . . . . .
H25 H 1.0173 0.8885 0.8515 0.067 Uiso 1 1 calc R U . . .
C23 C 0.7165(3) 1.0251(2) 0.73876(19) 0.0568(7) Uani 1 1 d . . . . .
H23 H 0.6557 1.0956 0.7452 0.068 Uiso 1 1 calc R U . . .
C29 C 0.7205(3) 0.3165(2) 0.41941(19) 0.0543(7) Uani 1 1 d . . . . .
H29 H 0.6547 0.3354 0.3607 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4116(4) 0.7536(3) -0.10279(19) 0.0617(8) Uani 1 1 d . . . . .
H9 H 0.3961 0.7769 -0.1695 0.074 Uiso 1 1 calc R U . . .
C8 C 0.2167(4) 0.5614(3) -0.14885(19) 0.0620(8) Uani 1 1 d . . . . .
H8 H 0.1994 0.5832 -0.2159 0.074 Uiso 1 1 calc R U . . .
C6 C 0.1580(3) 0.4178(2) -0.0233(2) 0.0560(7) Uani 1 1 d . . . . .
H6 H 0.1013 0.3432 -0.0061 0.067 Uiso 1 1 calc R U . . .
C7 C 0.1361(4) 0.4512(3) -0.1218(2) 0.0630(8) Uani 1 1 d . . . . .
H7 H 0.0657 0.3985 -0.1708 0.076 Uiso 1 1 calc R U . . .
C32 C 0.9072(4) 0.2572(3) 0.5930(2) 0.0659(8) Uani 1 1 d . . . . .
H32 H 0.9690 0.2367 0.6526 0.079 Uiso 1 1 calc R U . . .
C30 C 0.7637(4) 0.1955(2) 0.4293(2) 0.0661(8) Uani 1 1 d . . . . .
H30 H 0.7292 0.1329 0.3767 0.079 Uiso 1 1 calc R U . . .
C31 C 0.8578(4) 0.1650(3) 0.5163(2) 0.0702(9) Uani 1 1 d . . . . .
H31 H 0.8873 0.0823 0.5228 0.084 Uiso 1 1 calc R U . . .
C27 C 0.8909(4) 1.1053(3) 0.9018(2) 0.0749(9) Uani 1 1 d . . . . .
H27A H 0.8357 1.0782 0.9582 0.112 Uiso 1 1 calc R U . . .
H27B H 0.8556 1.1863 0.8834 0.112 Uiso 1 1 calc R U . . .
H27C H 1.0106 1.1133 0.9208 0.112 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 C19 1.331(4) . ?
N1 C20 1.329(3) . ?
N2 C20 1.336(4) . ?
N2 C17 1.339(4) . ?
C20 C28 1.469(4) . ?
C15 C12 1.411(4) . ?
C15 C16 1.417(4) . ?
C15 C11 1.410(4) . ?
C28 C29 1.376(4) . ?
C28 C33 1.385(4) . ?
C12 C3 1.404(4) . ?
C12 C4 1.427(4) . ?
C19 C18 1.378(4) . ?
C19 C21 1.474(4) . ?
C3 C2 1.382(4) . ?
C3 C17 1.480(4) . ?
C21 C22 1.376(4) . ?
C21 C26 1.383(4) . ?
C17 C18 1.370(4) . ?
C16 C13 1.403(4) . ?
C16 C14 1.415(4) . ?
C11 C1 1.390(4) . ?
C11 C10 1.435(4) . ?
C14 C8 1.385(4) . ?
C14 C9 1.411(4) . ?
C4 C5 1.346(4) . ?
C4 H4 0.9300 . ?
C13 C6 1.391(4) . ?
C13 C5 1.416(4) . ?
C18 H18 0.9300 . ?
C26 C25 1.369(4) . ?
C26 H26 0.9300 . ?
C1 C2 1.374(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C24 C25 1.372(4) . ?
C24 C23 1.369(4) . ?
C24 C27 1.502(4) . ?
C10 C9 1.320(4) . ?
C10 H10 0.9300 . ?
C33 C32 1.367(5) . ?
C33 H33 0.9300 . ?
C5 H5 0.9300 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?
C23 H23 0.9300 . ?
C29 C30 1.362(5) . ?
C29 H29 0.9300 . ?
C9 H9 0.9300 . ?
C8 C7 1.370(5) . ?
C8 H8 0.9300 . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C32 C31 1.361(5) . ?
C32 H32 0.9300 . ?
C30 C31 1.374(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C19 N1 C20 116.7(2) . . ?
C20 N2 C17 116.78(19) . . ?
N1 C20 N2 125.9(2) . . ?
N1 C20 C28 117.6(2) . . ?
N2 C20 C28 116.48(19) . . ?
C12 C15 C16 120.3(2) . . ?
C12 C15 C11 120.8(2) . . ?
C16 C15 C11 118.9(2) . . ?
C29 C28 C33 118.7(3) . . ?
C29 C28 C20 120.7(2) . . ?
C33 C28 C20 120.6(2) . . ?
C15 C12 C3 119.0(2) . . ?
C15 C12 C4 118.3(2) . . ?
C3 C12 C4 122.7(2) . . ?
N1 C19 C18 121.2(2) . . ?
N1 C19 C21 116.4(2) . . ?
C18 C19 C21 122.3(2) . . ?
C2 C3 C12 119.0(2) . . ?
C2 C3 C17 118.1(2) . . ?
C12 C3 C17 122.8(2) . . ?
C22 C21 C26 117.9(2) . . ?
C22 C21 C19 122.2(2) . . ?
C26 C21 C19 119.9(2) . . ?
N2 C17 C18 120.9(2) . . ?
N2 C17 C3 116.95(19) . . ?
C18 C17 C3 122.0(2) . . ?
C15 C16 C13 119.8(2) . . ?
C15 C16 C14 120.4(2) . . ?
C13 C16 C14 119.8(2) . . ?
C1 C11 C15 118.6(2) . . ?
C1 C11 C10 122.6(2) . . ?
C15 C11 C10 118.8(2) . . ?
C8 C14 C16 118.9(3) . . ?
C8 C14 C9 122.5(3) . . ?
C16 C14 C9 118.5(2) . . ?
C5 C4 C12 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C12 C4 H4 119.6 . . ?
C6 C13 C16 118.9(3) . . ?
C6 C13 C5 122.4(3) . . ?
C16 C13 C5 118.7(2) . . ?
C17 C18 C19 118.4(2) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C2 C1 C11 120.3(2) . . ?
C2 C1 H1 119.8 . . ?
C11 C1 H1 119.8 . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C25 C24 C23 117.8(2) . . ?
C25 C24 C27 121.9(3) . . ?
C23 C24 C27 120.3(3) . . ?
C9 C10 C11 121.6(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C32 C33 C28 120.1(2) . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
C4 C5 C13 121.9(2) . . ?
C4 C5 H5 119.0 . . ?
C13 C5 H5 119.0 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C26 C25 C24 121.6(3) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C22 C23 C24 121.3(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C10 C9 C14 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C14 C9 H9 119.1 . . ?
C14 C8 C7 120.8(3) . . ?
C14 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C6 C13 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C13 C6 H6 119.5 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C33 C32 C31 120.9(3) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C29 C30 C31 120.6(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 119.2(3) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.067

