# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_32081501_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2237834'
loop_
_audit_author_name
_audit_author_address
'Dra Berta Covelo'
;University of Vigo, Center for Scientific and Technological Research Support (CACTI)
Spain
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2021-12-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        
(E)-4-(amino((E)-phenyldiazenyl)methylene)-5-imino-N,N,1-trimethyl-4,5-dihydro-1H-imidazol-2-amine
_chemical_formula_moiety         'C16 H21 N7'
_chemical_formula_sum            'C16 H21 N7'
_chemical_formula_weight         311.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.6297(11)
_cell_length_b                   6.3019(6)
_cell_length_c                   12.7387(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.388(3)
_cell_angle_gamma                90
_cell_volume                     794.56(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9743
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7244
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1532 before and 0.0844 after correction.
The Ratio of minimum to maximum transmission is 0.8810.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.093
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.058
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec high brillance I\muS microsource'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2555
_reflns_number_total             2912
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2  (Sheldrick, 2018)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0785
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1295P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.1996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N13-H13
 0.88 with sigma of 0.02
 N2-H2A
 0.88 with sigma of 0.02
 N2-H2B
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15'(H15C,H15D), C16(H16A,H16B), C16'(H16C,H16D), C17(H17A,
 H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C10'(H10'), C11(H11), C11'(H11'), C12(H12)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.4995(5) 0.1787(7) 0.1666(4) 0.0231(11) Uani 1 1 d . . . . .
N2 N 0.5094(5) 0.6274(7) 0.4570(4) 0.0221(10) Uani 1 1 d D . . . .
H2A H 0.562(5) 0.737(7) 0.471(5) 0.026 Uiso 1 1 d D U . . .
H2B H 0.464(5) 0.672(9) 0.496(4) 0.026 Uiso 1 1 d D U . . .
N3 N 0.5867(4) 0.2824(7) 0.3497(4) 0.0209(10) Uani 1 1 d . . . . .
N7 N 0.3448(5) 0.7160(6) 0.2759(4) 0.0200(10) Uani 1 1 d . . . . .
N8 N 0.3162(5) 0.8720(7) 0.3275(4) 0.0198(10) Uani 1 1 d . . . . .
N13 N 0.3336(5) 0.4357(8) 0.0836(4) 0.0283(11) Uani 1 1 d D . . . .
H13 H 0.308(7) 0.560(6) 0.100(6) 0.034 Uiso 1 1 d D U . . .
N14 N 0.6810(5) -0.0199(7) 0.2964(4) 0.0242(11) Uani 1 1 d . . . . .
C2 C 0.5929(6) 0.1410(8) 0.2730(4) 0.0194(11) Uani 1 1 d . . . . .
C4 C 0.4844(5) 0.4232(9) 0.2913(4) 0.0195(11) Uani 1 1 d . . . . .
C5 C 0.4263(6) 0.3613(8) 0.1701(5) 0.0214(12) Uani 1 1 d . . . . .
C6 C 0.4469(5) 0.5908(8) 0.3429(5) 0.0179(11) Uani 1 1 d . . . . .
C9 C 0.2053(6) 0.9937(8) 0.2581(5) 0.0211(12) Uani 1 1 d . . . . .
C10 C 0.1069(6) 0.9201(9) 0.1588(5) 0.0249(13) Uani 1 1 d . . . . .
H10 H 0.112983 0.780938 0.132355 0.030 Uiso 1 1 calc R U . . .
C10' C 0.1950(6) 1.1986(8) 0.2960(4) 0.0227(12) Uani 1 1 d . . . . .
H10' H 0.260286 1.247521 0.364844 0.027 Uiso 1 1 calc R U . . .
C11 C 0.0009(6) 1.0503(10) 0.0992(5) 0.0294(14) Uani 1 1 d . . . . .
H11 H -0.066687 0.998882 0.032208 0.035 Uiso 1 1 calc R U . . .
C11' C 0.0900(6) 1.3312(8) 0.2336(5) 0.0270(13) Uani 1 1 d . . . . .
H11' H 0.085656 1.472778 0.257656 0.032 Uiso 1 1 calc R U . . .
C12 C -0.0091(6) 1.2546(10) 0.1352(5) 0.0328(15) Uani 1 1 d . . . . .
H12 H -0.083021 1.342341 0.093162 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7497(7) -0.0706(11) 0.2167(5) 0.0315(14) Uani 1 1 d . . . . .
H15A H 0.827248 0.026489 0.230134 0.038 Uiso 1 1 calc R U . . .
H15B H 0.686077 -0.049528 0.138301 0.038 Uiso 1 1 calc R U . . .
C15' C 0.7722(6) -0.0475(10) 0.4150(5) 0.0271(13) Uani 1 1 d . . . . .
H15C H 0.721986 -0.019764 0.465437 0.033 Uiso 1 1 calc R U . . .
H15D H 0.847241 0.055992 0.433168 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7986(7) -0.2955(11) 0.2319(5) 0.0352(15) Uani 1 1 d . . . . .
H16A H 0.844693 -0.326692 0.178688 0.042 Uiso 1 1 calc R U . . .
H16B H 0.720613 -0.392842 0.214873 0.042 Uiso 1 1 calc R U . . .
C16' C 0.8288(6) -0.2692(9) 0.4345(5) 0.0280(13) Uani 1 1 d . . . . .
H16C H 0.754703 -0.370282 0.427104 0.034 Uiso 1 1 calc R U . . .
H16D H 0.895514 -0.279931 0.512416 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8963(7) -0.3321(11) 0.3525(5) 0.0361(15) Uani 1 1 d . . . . .
H17A H 0.922640 -0.483545 0.363187 0.043 Uiso 1 1 calc R U . . .
H17B H 0.979011 -0.246372 0.367167 0.043 Uiso 1 1 calc R U . . .
C18 C 0.4441(7) 0.0235(9) 0.0747(5) 0.0304(14) Uani 1 1 d . . . . .
H18A H 0.485297 0.045529 0.018156 0.046 Uiso 1 1 calc R U . . .
H18B H 0.346012 0.042392 0.039553 0.046 Uiso 1 1 calc R U . . .
H18C H 0.463964 -0.120507 0.105264 0.046 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 C2 1.378(7) . ?
N1 C5 1.399(7) . ?
N1 C18 1.473(7) . ?
N2 H2A 0.87(3) . ?
N2 H2B 0.86(3) . ?
N2 C6 1.380(7) . ?
N3 C2 1.341(7) . ?
N3 C4 1.391(7) . ?
N7 N8 1.279(6) . ?
N7 C6 1.361(7) . ?
N8 C9 1.414(7) . ?
N13 H13 0.88(3) . ?
N13 C5 1.270(7) . ?
N14 C2 1.338(7) . ?
N14 C15 1.486(7) . ?
N14 C15' 1.478(7) . ?
C4 C5 1.490(7) . ?
C4 C6 1.377(7) . ?
C9 C10 1.394(8) . ?
C9 C10' 1.397(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(8) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.389(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(9) . ?
C11' H11' 0.9500 . ?
C11' C12 1.397(9) . ?
C12 H12 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.497(9) . ?
C15' H15C 0.9900 . ?
C15' H15D 0.9900 . ?
C15' C16' 1.505(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.526(9) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' C17 1.519(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C2 N1 C5 108.7(4) . . ?
C2 N1 C18 127.1(5) . . ?
C5 N1 C18 120.4(4) . . ?
H2A N2 H2B 95(6) . . ?
C6 N2 H2A 112(4) . . ?
C6 N2 H2B 121(4) . . ?
C2 N3 C4 105.7(4) . . ?
N8 N7 C6 114.1(4) . . ?
N7 N8 C9 113.3(4) . . ?
C5 N13 H13 109(4) . . ?
C2 N14 C15 119.3(5) . . ?
C2 N14 C15' 117.5(5) . . ?
C15' N14 C15 111.7(5) . . ?
N3 C2 N1 113.1(5) . . ?
N14 C2 N1 123.0(5) . . ?
N14 C2 N3 123.9(5) . . ?
N3 C4 C5 109.5(5) . . ?
C6 C4 N3 122.7(5) . . ?
C6 C4 C5 127.8(5) . . ?
N1 C5 C4 102.9(4) . . ?
N13 C5 N1 122.7(5) . . ?
N13 C5 C4 134.3(5) . . ?
N7 C6 N2 122.1(5) . . ?
N7 C6 C4 116.6(4) . . ?
C4 C6 N2 121.3(5) . . ?
C10 C9 N8 124.4(5) . . ?
C10 C9 C10' 119.6(5) . . ?
C10' C9 N8 116.0(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 H10 120.2 . . ?
C9 C10' H10' 119.8 . . ?
C11' C10' C9 120.4(5) . . ?
C11' C10' H10' 119.8 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C10' C11' H11' 120.3 . . ?
C10' C11' C12 119.4(5) . . ?
C12 C11' H11' 120.3 . . ?
C11 C12 C11' 119.6(6) . . ?
C11 C12 H12 120.2 . . ?
C11' C12 H12 120.2 . . ?
N14 C15 H15A 109.6 . . ?
N14 C15 H15B 109.6 . . ?
N14 C15 C16 110.4(5) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
N14 C15' H15C 109.5 . . ?
N14 C15' H15D 109.5 . . ?
N14 C15' C16' 110.6(5) . . ?
H15C C15' H15D 108.1 . . ?
C16' C15' H15C 109.5 . . ?
C16' C15' H15D 109.5 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C15 C16 C17 110.5(6) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15' C16' H16C 109.0 . . ?
C15' C16' H16D 109.0 . . ?
C15' C16' C17 112.9(5) . . ?
H16C C16' H16D 107.8 . . ?
C17 C16' H16C 109.0 . . ?
C17 C16' H16D 109.0 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
C16' C17 C16 109.5(5) . . ?
C16' C17 H17A 109.8 . . ?
C16' C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
N3 C4 C5 N1 1.4(5) . . . . ?
N3 C4 C5 N13 -179.8(6) . . . . ?
N3 C4 C6 N2 -0.4(8) . . . . ?
N3 C4 C6 N7 -179.8(5) . . . . ?
N7 N8 C9 C10 21.4(7) . . . . ?
N7 N8 C9 C10' -160.4(5) . . . . ?
N8 N7 C6 N2 2.2(7) . . . . ?
N8 N7 C6 C4 -178.5(5) . . . . ?
N8 C9 C10 C11 178.2(5) . . . . ?
N8 C9 C10' C11' 179.7(5) . . . . ?
N14 C15 C16 C17 -58.8(7) . . . . ?
N14 C15' C16' C17 53.8(7) . . . . ?
C2 N1 C5 N13 179.4(5) . . . . ?
C2 N1 C5 C4 -1.6(5) . . . . ?
C2 N3 C4 C5 -0.6(6) . . . . ?
C2 N3 C4 C6 179.1(5) . . . . ?
C2 N14 C15 C16 -157.8(5) . . . . ?
C2 N14 C15' C16' 160.5(5) . . . . ?
C4 N3 C2 N1 -0.4(6) . . . . ?
C4 N3 C2 N14 179.1(5) . . . . ?
C5 N1 C2 N3 1.3(6) . . . . ?
C5 N1 C2 N14 -178.1(5) . . . . ?
C5 C4 C6 N2 179.3(5) . . . . ?
C5 C4 C6 N7 -0.1(8) . . . . ?
C6 N7 N8 C9 -176.8(4) . . . . ?
C6 C4 C5 N1 -178.3(5) . . . . ?
C6 C4 C5 N13 0.5(10) . . . . ?
C9 C10 C11 C12 0.9(9) . . . . ?
C9 C10' C11' C12 3.0(8) . . . . ?
C10 C9 C10' C11' -2.0(8) . . . . ?
C10 C11 C12 C11' 0.1(9) . . . . ?
C10' C9 C10 C11 0.0(8) . . . . ?
C10' C11' C12 C11 -2.1(9) . . . . ?
C15 N14 C2 N1 41.9(7) . . . . ?
C15 N14 C2 N3 -137.5(6) . . . . ?
C15 N14 C15' C16' -56.3(6) . . . . ?
C15 C16 C17 C16' 55.2(7) . . . . ?
C15' N14 C2 N1 -177.7(5) . . . . ?
C15' N14 C2 N3 2.9(8) . . . . ?
C15' N14 C15 C16 59.6(7) . . . . ?
C15' C16' C17 C16 -53.2(7) . . . . ?
C18 N1 C2 N3 -156.2(5) . . . . ?
C18 N1 C2 N14 24.4(8) . . . . ?
C18 N1 C5 N13 -21.3(8) . . . . ?
C18 N1 C5 C4 157.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Heat-sensitive
