# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
R.B.P.Elmes
J.A.Kitchen
D.C.Williams
T.Gunnlaugsson
_publ_contact_author_name        'Jonathan A. Kitchen'
_publ_contact_author_email       JKITCHEN@tcd.ie

data_re87
_database_code_depnum_ccdc_archive 'CCDC 859051'
#TrackingRef '- Compound 2 X-ray.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 N6'
_chemical_formula_weight         336.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   15.066(3)
_cell_length_b                   7.0000(14)
_cell_length_c                   15.541(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.45(3)
_cell_angle_gamma                90.00
_cell_volume                     1563.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    4937
_cell_measurement_theta_min      1.3735
_cell_measurement_theta_max      30.7256

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4908
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      115(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10976
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         24.50
_reflns_number_total             2528
_reflns_number_gt                2088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1574P)^2^+3.8319P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2528
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.1357
_refine_ls_wR_factor_ref         0.3628
_refine_ls_wR_factor_gt          0.3368
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_restrained_S_all      1.246
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 1.0193(3) 0.7615(7) 1.0398(3) 0.0328(13) Uani 1 1 d . . .
N2 N 0.7942(3) 0.6333(7) 0.7468(3) 0.0312(12) Uani 1 1 d . . .
C6 C 0.8170(4) 0.6572(8) 0.8396(4) 0.0312(14) Uani 1 1 d . . .
N3 N 0.8794(4) 0.6629(7) 1.1212(4) 0.0364(13) Uani 1 1 d . . .
N1 N 0.9032(3) 0.5504(7) 0.5767(3) 0.0325(13) Uani 1 1 d . . .
N5 N 0.9745(3) 0.7559(7) 0.8495(3) 0.0319(13) Uani 1 1 d . . .
C9 C 0.8603(4) 0.6680(8) 1.0284(4) 0.0311(14) Uani 1 1 d . . .
C12 C 0.9327(4) 0.7142(8) 0.9888(4) 0.0303(14) Uani 1 1 d . . .
C4 C 0.7426(4) 0.6469(8) 0.5550(4) 0.0305(14) Uani 1 1 d . . .
H4 H 0.6973 0.6941 0.5809 0.037 Uiso 1 1 calc R . .
C13 C 0.9095(4) 0.7101(8) 0.8908(4) 0.0313(14) Uani 1 1 d . . .
N6 N 0.9813(3) 0.9631(8) 0.6531(3) 0.0363(13) Uani 1 1 d . . .
C3 C 0.7180(4) 0.6026(9) 0.4640(4) 0.0358(15) Uani 1 1 d . . .
H3 H 0.6562 0.6220 0.4261 0.043 Uiso 1 1 calc R . .
C11 C 1.0348(5) 0.7611(9) 1.1293(4) 0.0368(15) Uani 1 1 d . . .
H11 H 1.0944 0.7975 1.1674 0.044 Uiso 1 1 calc R . .
C7 C 0.7455(4) 0.6220(9) 0.8818(4) 0.0345(15) Uani 1 1 d . . .
H7 H 0.6835 0.5950 0.8464 0.041 Uiso 1 1 calc R . .
C1 C 0.8774(4) 0.5031(9) 0.4885(4) 0.0355(15) Uani 1 1 d . . .
H1 H 0.9231 0.4496 0.4648 0.043 Uiso 1 1 calc R . .
C15 C 0.8608(4) 0.6674(8) 0.7071(4) 0.0321(14) Uani 1 1 d . . .
C14 C 0.9495(4) 0.7412(9) 0.7585(4) 0.0310(14) Uani 1 1 d . . .
C5 C 0.8357(4) 0.6214(9) 0.6087(4) 0.0343(15) Uani 1 1 d . . .
C10 C 0.9648(4) 0.7078(9) 1.1693(4) 0.0376(16) Uani 1 1 d . . .
H10 H 0.9803 0.7046 1.2332 0.045 Uiso 1 1 calc R . .
C16 C 1.0176(4) 0.8228(8) 0.7143(4) 0.0318(14) Uani 1 1 d . . .
C20 C 1.0399(5) 1.0548(10) 0.6165(4) 0.0395(16) Uani 1 1 d . . .
H20 H 1.0155 1.1541 0.5744 0.047 Uiso 1 1 calc R . .
C8 C 0.7688(4) 0.6282(9) 0.9736(4) 0.0361(16) Uani 1 1 d . . .
H8 H 0.7219 0.6051 1.0017 0.043 Uiso 1 1 calc R . .
C19 C 1.1350(5) 1.0115(9) 0.6372(4) 0.0389(16) Uani 1 1 d . . .
H19 H 1.1740 1.0800 0.6099 0.047 Uiso 1 1 calc R . .
C2 C 0.7868(5) 0.5281(9) 0.4291(5) 0.0395(16) Uani 1 1 d . . .
H2 H 0.7727 0.4955 0.3672 0.047 Uiso 1 1 calc R . .
C18 C 1.1702(4) 0.8676(9) 0.6977(4) 0.0363(16) Uani 1 1 d . . .
H18 H 1.2341 0.8341 0.7124 0.044 Uiso 1 1 calc R . .
C17 C 1.1110(4) 0.7692(10) 0.7381(4) 0.0372(16) Uani 1 1 d . . .
H17 H 1.1341 0.6694 0.7803 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N4 0.034(3) 0.037(3) 0.028(3) -0.002(2) 0.012(2) -0.003(2)
N2 0.029(3) 0.030(3) 0.035(3) -0.002(2) 0.010(2) 0.000(2)
C6 0.033(3) 0.027(3) 0.034(3) 0.001(2) 0.010(3) 0.003(2)
N3 0.042(3) 0.031(3) 0.043(3) -0.004(2) 0.023(3) -0.003(2)
N1 0.022(3) 0.038(3) 0.037(3) -0.002(2) 0.009(2) 0.000(2)
N5 0.030(3) 0.030(3) 0.037(3) -0.003(2) 0.010(2) -0.003(2)
C9 0.038(3) 0.026(3) 0.032(3) -0.005(2) 0.014(3) -0.001(3)
C12 0.036(3) 0.023(3) 0.031(3) 0.006(2) 0.009(3) 0.005(2)
C4 0.029(3) 0.029(3) 0.033(3) 0.002(2) 0.008(3) 0.002(2)
C13 0.024(3) 0.031(3) 0.036(3) -0.001(3) 0.006(3) 0.000(2)
N6 0.029(3) 0.045(3) 0.037(3) 0.001(2) 0.014(2) -0.004(2)
C3 0.031(3) 0.032(3) 0.040(4) 0.003(3) 0.004(3) -0.006(3)
C11 0.037(3) 0.038(4) 0.036(4) -0.005(3) 0.011(3) 0.000(3)
C7 0.032(3) 0.031(3) 0.039(4) -0.002(3) 0.009(3) 0.002(3)
C1 0.032(3) 0.041(4) 0.032(3) -0.011(3) 0.008(3) 0.003(3)
C15 0.033(3) 0.028(3) 0.039(4) 0.000(3) 0.017(3) 0.007(2)
C14 0.029(3) 0.034(3) 0.033(3) -0.002(3) 0.013(3) 0.000(2)
C5 0.031(3) 0.039(4) 0.032(3) 0.003(3) 0.008(3) -0.006(3)
C10 0.043(4) 0.033(4) 0.037(4) 0.000(3) 0.011(3) 0.004(3)
C16 0.041(4) 0.027(3) 0.028(3) -0.004(2) 0.011(3) 0.001(3)
C20 0.045(4) 0.042(4) 0.034(4) 0.007(3) 0.014(3) -0.001(3)
C8 0.041(4) 0.028(3) 0.046(4) -0.001(3) 0.023(3) -0.004(3)
C19 0.046(4) 0.038(4) 0.043(4) -0.004(3) 0.029(3) -0.004(3)
C2 0.046(4) 0.038(4) 0.035(4) -0.007(3) 0.013(3) -0.006(3)
C18 0.027(3) 0.039(4) 0.046(4) -0.017(3) 0.015(3) -0.007(3)
C17 0.034(3) 0.045(4) 0.033(3) 0.002(3) 0.010(3) -0.001(3)

_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
N4 C11 1.340(8) . ?
N4 C12 1.350(8) . ?
N2 C15 1.348(8) . ?
N2 C6 1.389(8) . ?
C6 C13 1.431(8) . ?
C6 C7 1.439(8) . ?
N3 C10 1.317(8) . ?
N3 C9 1.384(8) . ?
N1 C1 1.350(8) . ?
N1 C5 1.353(8) . ?
N5 C14 1.354(8) . ?
N5 C13 1.361(8) . ?
C9 C8 1.414(9) . ?
C9 C12 1.440(8) . ?
C12 C13 1.457(8) . ?
C4 C3 1.386(9) . ?
C4 C5 1.412(8) . ?
C4 H4 0.9500 . ?
N6 C20 1.347(8) . ?
N6 C16 1.362(8) . ?
C3 C2 1.406(9) . ?
C3 H3 0.9500 . ?
C11 C10 1.425(9) . ?
C11 H11 0.9500 . ?
C7 C8 1.364(8) . ?
C7 H7 0.9500 . ?
C1 C2 1.410(9) . ?
C1 H1 0.9500 . ?
C15 C14 1.433(8) . ?
C15 C5 1.496(8) . ?
C14 C16 1.508(8) . ?
C10 H10 0.9500 . ?
C16 C17 1.394(9) . ?
C20 C19 1.405(9) . ?
C20 H20 0.9500 . ?
C8 H8 0.9500 . ?
C19 C18 1.372(9) . ?
C19 H19 0.9500 . ?
C2 H2 0.9500 . ?
C18 C17 1.415(9) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?

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
C11 N4 C12 116.5(5) . . ?
C15 N2 C6 117.9(5) . . ?
N2 C6 C13 120.3(5) . . ?
N2 C6 C7 117.8(5) . . ?
C13 C6 C7 121.9(5) . . ?
C10 N3 C9 116.6(5) . . ?
C1 N1 C5 116.4(5) . . ?
C14 N5 C13 117.4(5) . . ?
N3 C9 C8 118.9(5) . . ?
N3 C9 C12 120.2(5) . . ?
C8 C9 C12 120.9(5) . . ?
N4 C12 C9 121.8(5) . . ?
N4 C12 C13 120.3(5) . . ?
C9 C12 C13 117.9(5) . . ?
C3 C4 C5 119.3(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N5 C13 C6 121.2(6) . . ?
N5 C13 C12 120.5(5) . . ?
C6 C13 C12 118.3(5) . . ?
C20 N6 C16 117.5(5) . . ?
C4 C3 C2 118.3(6) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
N4 C11 C10 122.1(6) . . ?
N4 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C8 C7 C6 118.5(6) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N1 C1 C2 124.1(6) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
N2 C15 C14 120.5(5) . . ?
N2 C15 C5 115.8(5) . . ?
C14 C15 C5 123.7(5) . . ?
N5 C14 C15 122.0(5) . . ?
N5 C14 C16 115.7(5) . . ?
C15 C14 C16 122.1(5) . . ?
N1 C5 C4 123.5(6) . . ?
N1 C5 C15 117.8(5) . . ?
C4 C5 C15 118.6(6) . . ?
N3 C10 C11 122.6(6) . . ?
N3 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
N6 C16 C17 122.8(6) . . ?
N6 C16 C14 113.9(5) . . ?
C17 C16 C14 123.1(5) . . ?
N6 C20 C19 123.6(6) . . ?
N6 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
C7 C8 C9 122.3(6) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C18 C19 C20 118.2(6) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C3 C2 C1 118.4(6) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C19 C18 C17 119.8(6) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 118.1(6) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?

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
C15 N2 C6 C13 -2.1(8) . . . . ?
C15 N2 C6 C7 179.6(5) . . . . ?
C10 N3 C9 C8 -177.6(6) . . . . ?
C10 N3 C9 C12 2.1(8) . . . . ?
C11 N4 C12 C9 0.7(8) . . . . ?
C11 N4 C12 C13 -179.8(5) . . . . ?
N3 C9 C12 N4 -2.9(9) . . . . ?
C8 C9 C12 N4 176.8(5) . . . . ?
N3 C9 C12 C13 177.6(5) . . . . ?
C8 C9 C12 C13 -2.7(9) . . . . ?
C14 N5 C13 C6 -2.9(8) . . . . ?
C14 N5 C13 C12 177.2(5) . . . . ?
N2 C6 C13 N5 6.4(9) . . . . ?
C7 C6 C13 N5 -175.4(5) . . . . ?
N2 C6 C13 C12 -173.7(5) . . . . ?
C7 C6 C13 C12 4.5(9) . . . . ?
N4 C12 C13 N5 -0.7(9) . . . . ?
C9 C12 C13 N5 178.8(5) . . . . ?
N4 C12 C13 C6 179.4(5) . . . . ?
C9 C12 C13 C6 -1.1(8) . . . . ?
C5 C4 C3 C2 1.8(9) . . . . ?
C12 N4 C11 C10 2.0(9) . . . . ?
N2 C6 C7 C8 174.3(5) . . . . ?
C13 C6 C7 C8 -4.0(9) . . . . ?
C5 N1 C1 C2 1.8(9) . . . . ?
C6 N2 C15 C14 -5.1(8) . . . . ?
C6 N2 C15 C5 174.2(5) . . . . ?
C13 N5 C14 C15 -4.5(9) . . . . ?
C13 N5 C14 C16 170.5(5) . . . . ?
N2 C15 C14 N5 8.8(9) . . . . ?
C5 C15 C14 N5 -170.5(6) . . . . ?
N2 C15 C14 C16 -165.9(5) . . . . ?
C5 C15 C14 C16 14.8(9) . . . . ?
C1 N1 C5 C4 0.0(9) . . . . ?
C1 N1 C5 C15 177.4(5) . . . . ?
C3 C4 C5 N1 -1.7(9) . . . . ?
C3 C4 C5 C15 -179.2(5) . . . . ?
N2 C15 C5 N1 -144.1(6) . . . . ?
C14 C15 C5 N1 35.2(9) . . . . ?
N2 C15 C5 C4 33.5(8) . . . . ?
C14 C15 C5 C4 -147.2(6) . . . . ?
C9 N3 C10 C11 0.5(9) . . . . ?
N4 C11 C10 N3 -2.8(10) . . . . ?
C20 N6 C16 C17 -1.5(9) . . . . ?
C20 N6 C16 C14 174.3(5) . . . . ?
N5 C14 C16 N6 -121.1(6) . . . . ?
C15 C14 C16 N6 53.9(8) . . . . ?
N5 C14 C16 C17 54.6(8) . . . . ?
C15 C14 C16 C17 -130.4(7) . . . . ?
C16 N6 C20 C19 0.9(9) . . . . ?
C6 C7 C8 C9 0.0(9) . . . . ?
N3 C9 C8 C7 -177.0(6) . . . . ?
C12 C9 C8 C7 3.4(9) . . . . ?
N6 C20 C19 C18 0.2(10) . . . . ?
C4 C3 C2 C1 -0.2(9) . . . . ?
N1 C1 C2 C3 -1.6(10) . . . . ?
C20 C19 C18 C17 -0.8(9) . . . . ?
N6 C16 C17 C18 1.0(9) . . . . ?
C14 C16 C17 C18 -174.4(5) . . . . ?
C19 C18 C17 C16 0.2(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        24.50
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.100