# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1507101'
_audit_update_record             
;
2016-09-28 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H14 N4'
_chemical_formula_sum            'C24 H14 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         358.39

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5761(7)
_cell_length_b                   5.7765(5)
_cell_length_c                   18.0007(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.358(3)
_cell_angle_gamma                90
_cell_volume                     890.22(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1882
_cell_measurement_theta_min      3.705
_cell_measurement_theta_max      26.535
_cell_measurement_temperature    150(1)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.126
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'


_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150(1)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'KappaCCD APEXII Diffractometer'
_diffrn_measurement_method       'Phi plus Omega scan'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            5273
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_full        26.48
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             1810
_reflns_number_gt                1382
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1479
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_number_reflns         1810
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0863P)²+0.0983P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N2 0.84733(14) 0.2158(2) 0.50042(7) 0.0321(4) Uani d . . . 1 . .
N N1 -0.12252(14) 0.1911(2) 0.26735(7) 0.0340(4) Uani d . . . 1 . .
C C1 -0.06343(17) 0.3650(3) 0.30875(8) 0.0332(4) Uani d . . . 1 . .
H H1 -0.1255 0.5001 0.3131 0.04 Uiso calc U . R 1 . .
C C2 0.08332(16) 0.3613(3) 0.34602(9) 0.0313(4) Uani d . . . 1 . .
H H2 0.1191 0.489 0.3756 0.038 Uiso calc U . R 1 . .
C C3 0.17645(15) 0.1663(3) 0.33905(8) 0.0265(4) Uani d . . . 1 . .
C C6 0.33114(16) 0.1503(3) 0.37333(8) 0.0293(4) Uani d . . . 1 . .
C C7 0.46213(16) 0.1275(3) 0.39924(8) 0.0313(4) Uani d . . . 1 . .
C C8 0.61869(15) 0.0854(3) 0.42833(8) 0.0287(4) Uani d . . . 1 . .
C C12 0.70122(17) 0.2469(3) 0.47283(9) 0.0335(4) Uani d . . . 1 . .
H H12 0.6502 0.3875 0.4841 0.04 Uiso calc U . R 1 . .
C C11 0.91796(14) 0.0152(2) 0.48493(7) 0.0252(4) Uani d . . . 1 . .
C C10 0.84323(16) -0.1582(3) 0.44342(8) 0.0308(4) Uani d . . . 1 . .
H H10 0.8951 -0.3004 0.4351 0.037 Uiso calc U . R 1 . .
C C9 0.69323(17) -0.1230(3) 0.41435(8) 0.0341(4) Uani d . . . 1 . .
H H9 0.6411 -0.2395 0.3851 0.041 Uiso calc U . R 1 . .
C C5 -0.03266(17) 0.0041(3) 0.26219(8) 0.0342(4) Uani d . . . 1 . .
H H5 -0.0733 -0.1231 0.2338 0.041 Uiso calc U . R 1 . .
C C4 0.11604(17) -0.0163(3) 0.29564(8) 0.0308(4) Uani d . . . 1 . .
H H4 0.176 -0.1523 0.2892 0.037 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N2 C12 . 1.3328(18) ?
N2 C11 . 1.3441(19) ?
N1 C1 . 1.333(2) ?
N1 C5 . 1.333(2) ?
C1 C2 . 1.3912(19) ?
C1 H1 . 0.95 ?
C2 C3 . 1.391(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.394(2) ?
C3 C6 . 1.4330(17) ?
C6 C7 . 1.198(2) ?
C7 C8 . 1.4331(18) ?
C8 C9 . 1.393(2) ?
C8 C12 . 1.395(2) ?
C12 H12 . 0.95 ?
C11 C10 . 1.385(2) ?
C11 C11 3_756 1.488(2) ?
C10 C9 . 1.3752(19) ?
C10 H10 . 0.95 ?
C9 H9 . 0.95 ?
C5 C4 . 1.3831(19) ?
C5 H5 . 0.95 ?
C4 H4 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 N2 C11 . . 117.67(12) ?
C1 N1 C5 . . 116.56(13) ?
N1 C1 C2 . . 124.15(14) ?
N1 C1 H1 . . 117.9 ?
C2 C1 H1 . . 117.9 ?
C3 C2 C1 . . 118.50(13) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 117.82(13) ?
C2 C3 C6 . . 122.37(13) ?
C4 C3 C6 . . 119.79(13) ?
C7 C6 C3 . . 176.37(16) ?
C6 C7 C8 . . 176.33(17) ?
C9 C8 C12 . . 117.32(13) ?
C9 C8 C7 . . 120.71(14) ?
C12 C8 C7 . . 121.95(14) ?
N2 C12 C8 . . 123.91(14) ?
N2 C12 H12 . . 118.0 ?
C8 C12 H12 . . 118.0 ?
N2 C11 C10 . . 122.39(13) ?
N2 C11 C11 . 3_756 117.00(16) ?
C10 C11 C11 . 3_756 120.61(16) ?
C9 C10 C11 . . 119.44(14) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
C10 C9 C8 . . 119.21(14) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
N1 C5 C4 . . 124.10(14) ?
N1 C5 H5 . . 118.0 ?
C4 C5 H5 . . 118.0 ?
C5 C4 C3 . . 118.84(14) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -0.1(2) ?
N1 C1 C2 C3 . . . . 1.2(2) ?
C1 C2 C3 C4 . . . . -0.8(2) ?
C1 C2 C3 C6 . . . . 177.83(13) ?
C11 N2 C12 C8 . . . . -0.8(2) ?
C9 C8 C12 N2 . . . . 2.1(2) ?
C7 C8 C12 N2 . . . . -179.34(14) ?
C12 N2 C11 C10 . . . . -1.5(2) ?
C12 N2 C11 C11 . . . 3_756 178.97(14) ?
N2 C11 C10 C9 . . . . 2.4(2) ?
C11 C11 C10 C9 3_756 . . . -178.07(15) ?
C11 C10 C9 C8 . . . . -1.0(2) ?
C12 C8 C9 C10 . . . . -1.1(2) ?
C7 C8 C9 C10 . . . . -179.68(13) ?
C1 N1 C5 C4 . . . . -1.2(2) ?
N1 C5 C4 C3 . . . . 1.5(2) ?
C2 C3 C4 C5 . . . . -0.4(2) ?
C6 C3 C4 C5 . . . . -179.09(13) ?

_shelxl_version_number           2014-3

