# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Py-BiimzH2
_database_code_depnum_ccdc_archive 'CCDC 1040155'
_audit_update_record             
;
2014-12-20 deposited with the CCDC.
2015-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 N4'
_chemical_formula_weight         308.34

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.0572(15)
_cell_length_b                   15.3589(11)
_cell_length_c                   9.5549(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2943.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1116
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      17.26

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8322
_exptl_absorpt_correction_T_max  0.94398
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29082
_diffrn_reflns_av_R_equivalents  0.1306
_diffrn_reflns_av_sigmaI/netI    0.0792
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2593
_reflns_number_gt                1447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2593
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1907
_refine_ls_wR_factor_gt          0.1545
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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 -0.05256(13) 0.27735(16) 0.5999(3) 0.0392(7) Uani 1 1 d . . .
N1 N -0.18688(15) 0.19573(19) 0.5821(3) 0.0525(8) Uani 1 1 d . . .
N3 N -0.06386(14) 0.31620(18) 0.3756(3) 0.0438(7) Uani 1 1 d . . .
H3N H -0.0787 0.3197 0.2914 0.053 Uiso 1 1 calc R . .
C14 C 0.14567(18) 0.4682(2) 0.6709(5) 0.0540(10) Uani 1 1 d . . .
C19 C 0.09525(16) 0.4278(2) 0.5882(4) 0.0444(9) Uani 1 1 d . . .
C18 C 0.05306(16) 0.3649(2) 0.6531(3) 0.0425(9) Uani 1 1 d . . .
C5 C 0.00069(16) 0.3319(2) 0.5665(3) 0.0393(8) Uani 1 1 d . . .
C4 C -0.09039(17) 0.2725(2) 0.4806(3) 0.0379(8) Uani 1 1 d . . .
C3 C -0.15574(17) 0.2336(2) 0.4765(3) 0.0406(8) Uani 1 1 d . . .
C11 C 0.13114(19) 0.5133(2) 0.3829(5) 0.0597(11) Uani 1 1 d . . .
C10 C 0.1230(3) 0.5356(3) 0.2430(6) 0.0757(14) Uani 1 1 d . . .
H10 H 0.1524 0.5750 0.2022 0.091 Uiso 1 1 calc R . .
C7 C 0.03619(17) 0.4151(2) 0.3598(4) 0.0450(9) Uani 1 1 d . . .
C6 C -0.00790(16) 0.3547(2) 0.4287(3) 0.0390(8) Uani 1 1 d . . .
C17 C 0.06280(18) 0.3424(2) 0.7928(4) 0.0526(10) Uani 1 1 d . . .
H17 H 0.0360 0.3003 0.8342 0.063 Uiso 1 1 calc R . .
C20 C 0.08763(17) 0.4514(2) 0.4435(4) 0.0469(9) Uani 1 1 d . . .
N2 N -0.19564(14) 0.24173(17) 0.3637(3) 0.0439(7) Uani 1 1 d . . .
H2N H -0.1852 0.2648 0.2847 0.053 Uiso 1 1 calc R . .
C15 C 0.1519(2) 0.4458(3) 0.8107(5) 0.0659(12) Uani 1 1 d . . .
H15 H 0.1835 0.4740 0.8656 0.079 Uiso 1 1 calc R . .
C1 C -0.24983(19) 0.1792(3) 0.5318(4) 0.0600(11) Uani 1 1 d . . .
H1 H -0.2837 0.1527 0.5830 0.072 Uiso 1 1 calc R . .
C12 C 0.1820(2) 0.5517(2) 0.4692(6) 0.0741(14) Uani 1 1 d . . .
H12 H 0.2110 0.5920 0.4298 0.089 Uiso 1 1 calc R . .
C9 C 0.0724(3) 0.5008(3) 0.1632(5) 0.0747(13) Uani 1 1 d . . .
H9 H 0.0674 0.5175 0.0702 0.090 Uiso 1 1 calc R . .
C8 C 0.0289(2) 0.4410(2) 0.2214(4) 0.0590(11) Uani 1 1 d . . .
H8 H -0.0055 0.4181 0.1675 0.071 Uiso 1 1 calc R . .
C16 C 0.11209(19) 0.3826(3) 0.8698(4) 0.0639(12) Uani 1 1 d . . .
H16 H 0.1186 0.3669 0.9628 0.077 Uiso 1 1 calc R . .
C13 C 0.1886(2) 0.5311(3) 0.6043(6) 0.0720(13) Uani 1 1 d . . .
H13 H 0.2218 0.5580 0.6568 0.086 Uiso 1 1 calc R . .
C2 C -0.25593(18) 0.2064(2) 0.3988(4) 0.0566(10) Uani 1 1 d . . .
H2 H -0.2935 0.2020 0.3421 0.068 Uiso 1 1 calc R . .


_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 C4 1.371(4) . ?
N4 C5 1.395(4) . ?
N1 C3 1.322(4) . ?
N1 C1 1.375(4) . ?
N3 C4 1.319(4) . ?
N3 C6 1.367(4) . ?
N3 H3N 0.8600 . ?
C14 C15 1.384(5) . ?
C14 C19 1.425(5) . ?
C14 C13 1.442(5) . ?
C19 C18 1.426(4) . ?
C19 C20 1.438(5) . ?
C18 C17 1.393(4) . ?
C18 C5 1.430(4) . ?
C5 C6 1.373(4) . ?
C4 C3 1.441(5) . ?
C3 N2 1.348(4) . ?
C11 C10 1.390(6) . ?
C11 C20 1.414(5) . ?
C11 C12 1.438(6) . ?
C10 C9 1.378(6) . ?
C10 H10 0.9300 . ?
C7 C8 1.389(5) . ?
C7 C20 1.419(5) . ?
C7 C6 1.440(4) . ?
C17 C16 1.379(5) . ?
C17 H17 0.9300 . ?
N2 C2 1.367(4) . ?
N2 H2N 0.8600 . ?
C15 C16 1.378(5) . ?
C15 H15 0.9300 . ?
C1 C2 1.343(5) . ?
C1 H1 0.9300 . ?
C12 C13 1.336(6) . ?
C12 H12 0.9300 . ?
C9 C8 1.383(5) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C2 H2 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
C4 N4 C5 105.5(3) . . ?
C3 N1 C1 104.4(3) . . ?
C4 N3 C6 105.6(3) . . ?
C4 N3 H3N 127.2 . . ?
C6 N3 H3N 127.2 . . ?
C15 C14 C19 119.4(4) . . ?
C15 C14 C13 122.5(4) . . ?
C19 C14 C13 118.1(4) . . ?
C14 C19 C18 118.3(3) . . ?
C14 C19 C20 119.9(3) . . ?
C18 C19 C20 121.7(3) . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 C5 124.7(3) . . ?
C19 C18 C5 115.1(3) . . ?
C6 C5 N4 106.0(3) . . ?
C6 C5 C18 123.8(3) . . ?
N4 C5 C18 130.0(3) . . ?
N3 C4 N4 112.4(3) . . ?
N3 C4 C3 123.8(3) . . ?
N4 C4 C3 123.3(3) . . ?
N1 C3 N2 111.7(3) . . ?
N1 C3 C4 126.2(3) . . ?
N2 C3 C4 121.6(3) . . ?
C10 C11 C20 119.2(4) . . ?
C10 C11 C12 122.2(4) . . ?
C20 C11 C12 118.6(4) . . ?
C9 C10 C11 121.5(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C8 C7 C20 120.0(3) . . ?
C8 C7 C6 123.7(3) . . ?
C20 C7 C6 116.2(3) . . ?
N3 C6 C5 110.4(3) . . ?
N3 C6 C7 127.8(3) . . ?
C5 C6 C7 121.7(3) . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C11 C20 C7 118.8(4) . . ?
C11 C20 C19 119.8(4) . . ?
C7 C20 C19 121.3(3) . . ?
C3 N2 C2 107.0(3) . . ?
C3 N2 H2N 126.5 . . ?
C2 N2 H2N 126.5 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C2 C1 N1 110.9(3) . . ?
C2 C1 H1 124.5 . . ?
N1 C1 H1 124.5 . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C15 C16 C17 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C13 C14 121.7(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C1 C2 N2 105.9(3) . . ?
C1 C2 H2 127.0 . . ?
N2 C2 H2 127.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.049
