# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
# 
#######################################################################

data_mo_IAPAAB42_0m_b1
_database_code_depnum_ccdc_archive 'CCDC 2216961'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2022-12-21 downloaded from the CCDC.
;

_vrf_PLAT111_mo_IAPAAB42_0m_b1   
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry
RESPONSE: The proposed symmetry centre is not valid as the CN group in a 
nitrile at one end and an isonitrile at the other end, as indicated by 13C NMR.
;
# end Validation Reply Form 
_vrf_PLAT113_mo_IAPAAB42_0m_b1   
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group
RESPONSE: The proposed symmetry centre is not valid as the CN group in a 
nitrile at one end and an isonitrile at the other end, as indicated by 13C NMR.
;
# end Validation Reply Form 
_vrf_PLAT315_mo_IAPAAB42_0m_b1   
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).
RESPONSE: The C14 atom does not have an hydrogen atom attached as it 
is part from an isonitrile group
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 N4'
_chemical_formula_sum            'C14 H8 N4'
_chemical_formula_weight         232.24

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -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'

_cell_length_a                   4.6702(3)
_cell_length_b                   10.4251(7)
_cell_length_c                   11.8640(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.307(3)
_cell_angle_gamma                90
_cell_volume                     571.57(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5812
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.53

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11648
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.953
_diffrn_reflns_theta_max         30.589
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             3143
_reflns_number_gt                2705
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.790
_reflns_Friedel_fraction_full    0.870

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.2131P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3143
_refine_ls_number_parameters     164
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_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 -0.5816(9) -0.2206(3) 0.3399(4) 0.0311(8) Uani 1 1 d . U . . .
N2 N 0.4715(6) 0.2046(3) 0.5340(3) 0.0176(6) Uani 1 1 d . . . . .
N3 N 0.5174(7) 0.2945(3) 0.4685(3) 0.0224(7) Uani 1 1 d . . . . .
N4 N 1.3900(6) 0.6460(3) 0.6308(3) 0.0218(6) Uani 1 1 d . U . . .
C1 C -0.3992(8) -0.1465(3) 0.3722(3) 0.0182(6) Uani 1 1 d . U . . .
C2 C -0.1854(7) -0.0572(3) 0.4111(3) 0.0155(6) Uani 1 1 d . . . . .
C3 C -0.0386(9) -0.0663(4) 0.5225(3) 0.0215(8) Uani 1 1 d . . . . .
H3 H -0.086009 -0.130370 0.571106 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1784(8) 0.0215(3) 0.5596(3) 0.0190(7) Uani 1 1 d . . . . .
H4 H 0.281310 0.015083 0.632621 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2418(8) 0.1206(3) 0.4860(3) 0.0192(7) Uani 1 1 d . U . . .
C6 C 0.0943(7) 0.1314(3) 0.3769(3) 0.0200(7) Uani 1 1 d . U . . .
H6 H 0.137899 0.197630 0.329746 0.024 Uiso 1 1 calc R U . . .
C7 C -0.1202(9) 0.0427(3) 0.3378(3) 0.0213(8) Uani 1 1 d . . . . .
H7 H -0.219810 0.048972 0.264287 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7417(7) 0.3793(3) 0.5155(3) 0.0163(6) Uani 1 1 d . U . . .
C9 C 0.8097(9) 0.4752(4) 0.4447(3) 0.0221(8) Uani 1 1 d . . . . .
H9 H 0.712921 0.479591 0.370535 0.026 Uiso 1 1 calc R U . . .
C10 C 1.0200(8) 0.5656(4) 0.4816(3) 0.0187(7) Uani 1 1 d . . . . .
H10 H 1.060782 0.632123 0.434172 0.022 Uiso 1 1 calc R U . . .
C11 C 1.1685(7) 0.5543(3) 0.5915(3) 0.0188(7) Uani 1 1 d . . . . .
C12 C 1.1087(8) 0.4577(3) 0.6637(3) 0.0189(7) Uani 1 1 d . . . . .
H12 H 1.211642 0.452001 0.736727 0.023 Uiso 1 1 calc R U . . .
C13 C 0.8958(8) 0.3696(4) 0.6273(3) 0.0210(7) Uani 1 1 d . U . . .
H13 H 0.853428 0.304244 0.675622 0.025 Uiso 1 1 calc R U . . .
C14 C 1.5664(9) 0.7211(3) 0.6621(3) 0.0222(7) Uani 1 1 d . 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 C1 1.172(5) . ?
N2 N3 1.2551(19) . ?
N2 C5 1.437(4) . ?
N3 C8 1.422(4) . ?
N4 C14 1.158(5) . ?
N4 C11 1.436(4) . ?
C1 C2 1.394(5) . ?
C2 C3 1.402(5) . ?
C2 C7 1.418(4) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.412(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C6 C7 1.393(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.373(5) . ?
C8 C13 1.418(5) . ?
C9 C10 1.386(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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
N3 N2 C5 113.2(2) . . ?
N2 N3 C8 113.8(2) . . ?
C14 N4 C11 179.2(4) . . ?
N1 C1 C2 179.1(4) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 C7 119.6(3) . . ?
C3 C2 C7 120.6(3) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 N2 124.4(3) . . ?
C4 C5 N2 114.3(3) . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C9 C8 C13 119.6(3) . . ?
C9 C8 N3 115.8(3) . . ?
C13 C8 N3 124.6(3) . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 N4 119.1(3) . . ?
C10 C11 N4 119.1(3) . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?

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
C5 N2 N3 C8 179.2(4) . . . . ?
C1 C2 C3 C4 178.6(3) . . . . ?
C7 C2 C3 C4 -2.0(6) . . . . ?
C2 C3 C4 C5 1.9(6) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C3 C4 C5 N2 -179.7(3) . . . . ?
N3 N2 C5 C6 3.4(4) . . . . ?
N3 N2 C5 C4 -177.7(3) . . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
N2 C5 C6 C7 178.4(3) . . . . ?
C5 C6 C7 C2 0.4(6) . . . . ?
C1 C2 C7 C6 -179.8(3) . . . . ?
C3 C2 C7 C6 0.8(6) . . . . ?
N2 N3 C8 C9 176.7(3) . . . . ?
N2 N3 C8 C13 -2.5(4) . . . . ?
C13 C8 C9 C10 -2.2(6) . . . . ?
N3 C8 C9 C10 178.5(3) . . . . ?
C8 C9 C10 C11 2.2(6) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C9 C10 C11 N4 179.1(3) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
N4 C11 C12 C13 179.6(3) . . . . ?
C11 C12 C13 C8 0.3(6) . . . . ?
C9 C8 C13 C12 0.9(6) . . . . ?
N3 C8 C13 C12 -179.8(3) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.047



