# Electronic Supplementary Material (ESI) for ChemComm.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1420746'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N8 O2 Zn2'
_chemical_formula_weight         583.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.008 0.889 0.000 2395 899 ' '
_platon_squeeze_details          ?

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(3)22

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
'-x, y, -z'
'x, -y, -z+1/2'
'y, x, -z+1/4'
'-y, -x, -z+3/4'

_cell_length_a                   11.69630(10)
_cell_length_b                   11.69630(10)
_cell_length_c                   47.2239(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6460.39(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    6509
_cell_measurement_theta_min      3.7140
_cell_measurement_theta_max      70.7830

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2368
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies,Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)(compiled May 22 2014,16:03:01)Empirical absorption correction using spherical harmonics,implemented in SCALE3 ABSPACK scaling algorithm.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12559
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         71.17
_reflns_number_total             6101
_reflns_number_gt                5577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1200P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_number_reflns         6101
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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
Zn1 Zn 0.29504(4) 0.24044(5) 0.004933(10) 0.04145(16) Uani 1 1 d . . .
Zn2 Zn 0.5000 0.03295(6) 0.0000 0.03821(19) Uani 1 2 d S . .
Zn3 Zn 0.5000 0.44962(6) 0.0000 0.0427(2) Uani 1 2 d S . .
N4 N -0.1609(3) 0.2178(3) -0.21264(7) 0.0421(7) Uani 1 1 d . . .
N1 N 0.1841(3) 0.3039(3) -0.02354(7) 0.0398(7) Uani 1 1 d . . .
O1 O 0.3752(3) 0.1210(3) -0.01645(6) 0.0531(7) Uani 1 1 d . . .
N5 N 0.4423(3) -0.0671(3) 0.03167(6) 0.0425(7) Uani 1 1 d . . .
C19 C 0.5302(3) -0.2859(3) 0.15156(7) 0.0385(8) Uani 1 1 d . . .
C12 C -0.1412(3) 0.2687(3) -0.18804(7) 0.0383(7) Uani 1 1 d . . .
H12A H -0.1693 0.3403 -0.1830 0.046 Uiso 1 1 calc R . .
N6 N 0.4374(3) -0.1646(3) 0.07145(7) 0.0421(7) Uani 1 1 d . . .
N8 N 0.5371(3) -0.4168(3) 0.22009(7) 0.0413(7) Uani 1 1 d . . .
C15 C 0.4978(4) -0.0890(3) 0.05550(7) 0.0415(8) Uani 1 1 d . . .
H15A H 0.5678 -0.0573 0.0606 0.050 Uiso 1 1 calc R . .
C13 C 0.3414(4) -0.1288(4) 0.03263(9) 0.0483(10) Uani 1 1 d . . .
H13A H 0.2851 -0.1291 0.0187 0.058 Uiso 1 1 calc R . .
N2 N 0.0910(3) 0.3192(3) -0.06333(7) 0.0419(7) Uani 1 1 d . . .
N3 N -0.0751(3) 0.2029(3) -0.17139(7) 0.0417(7) Uani 1 1 d . . .
N7 N 0.5566(3) -0.3286(3) 0.17902(7) 0.0394(7) Uani 1 1 d . . .
C8 C -0.0922(5) 0.3045(5) -0.12697(10) 0.0664(16) Uani 1 1 d . . .
H8A H -0.1600 0.3357 -0.1338 0.080 Uiso 1 1 calc R . .
C7 C -0.0330(4) 0.2326(4) -0.14358(8) 0.0439(8) Uani 1 1 d . . .
C24 C 0.4892(3) -0.3946(3) 0.19510(7) 0.0375(8) Uani 1 1 d . . .
H24A H 0.4179 -0.4215 0.1895 0.045 Uiso 1 1 calc R . .
C2 C 0.1282(4) 0.4067(4) -0.02388(9) 0.0520(10) Uani 1 1 d . . .
H2A H 0.1311 0.4608 -0.0095 0.062 Uiso 1 1 calc R . .
C11 C -0.1060(4) 0.1131(4) -0.21138(10) 0.0535(11) Uani 1 1 d . . .
H11A H -0.1049 0.0588 -0.2257 0.064 Uiso 1 1 calc R . .
C10 C -0.0551(5) 0.1027(4) -0.18635(10) 0.0604(13) Uani 1 1 d . . .
H10A H -0.0137 0.0398 -0.1800 0.072 Uiso 1 1 calc R . .
C1 C 0.0676(4) 0.4185(4) -0.04837(9) 0.0516(10) Uani 1 1 d . . .
H1A H 0.0213 0.4792 -0.0538 0.062 Uiso 1 1 calc R . .
C4 C 0.0469(3) 0.2888(3) -0.09140(8) 0.0422(8) Uani 1 1 d . . .
C17 C 0.5436(5) -0.1453(4) 0.11533(10) 0.0599(13) Uani 1 1 d . . .
H17A H 0.5743 -0.0769 0.1087 0.072 Uiso 1 1 calc R . .
C3 C 0.1607(3) 0.2541(4) -0.04824(8) 0.0401(8) Uani 1 1 d . . .
H3A H 0.1893 0.1837 -0.0541 0.048 Uiso 1 1 calc R . .
C16 C 0.4709(4) -0.2062(3) 0.09844(7) 0.0401(8) Uani 1 1 d . . .
C20 C 0.4547(5) -0.3484(5) 0.13449(11) 0.0633(13) Uani 1 1 d . . .
H20A H 0.4238 -0.4167 0.1411 0.076 Uiso 1 1 calc R . .
C21 C 0.4264(5) -0.3088(4) 0.10812(9) 0.0570(12) Uani 1 1 d . . .
H21A H 0.3772 -0.3508 0.0967 0.068 Uiso 1 1 calc R . .
C5 C 0.1106(4) 0.2191(5) -0.10833(11) 0.0592(12) Uani 1 1 d . . .
H5A H 0.1811 0.1917 -0.1023 0.071 Uiso 1 1 calc R . .
C14 C 0.3383(4) -0.1878(4) 0.05686(9) 0.0529(11) Uani 1 1 d . . .
H14A H 0.2796 -0.2359 0.0628 0.063 Uiso 1 1 calc R . .
C9 C -0.0557(5) 0.3337(4) -0.09999(11) 0.0612(13) Uani 1 1 d . . .
H9A H -0.0986 0.3814 -0.0883 0.073 Uiso 1 1 calc R . .
C22 C 0.6536(4) -0.3065(4) 0.19500(10) 0.0554(11) Uani 1 1 d . . .
H22A H 0.7156 -0.2616 0.1897 0.067 Uiso 1 1 calc R . .
C6 C 0.0680(5) 0.1896(5) -0.13488(11) 0.0638(13) Uani 1 1 d . . .
H6A H 0.1091 0.1404 -0.1466 0.077 Uiso 1 1 calc R . .
C23 C 0.6407(4) -0.3621(5) 0.21954(10) 0.0573(12) Uani 1 1 d . . .
H23A H 0.6942 -0.3636 0.2341 0.069 Uiso 1 1 calc R . .
C18 C 0.5726(5) -0.1844(5) 0.14252(10) 0.0678(16) Uani 1 1 d . . .
H18A H 0.6201 -0.1412 0.1542 0.081 Uiso 1 1 calc R . .
O2 O 0.3947(4) 0.3531(4) 0.02100(8) 0.0752(11) Uani 1 1 d . . .


_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
Zn1 O2 1.916(4) . ?
Zn1 O1 1.962(3) . ?
Zn1 N4 2.006(3) 4 ?
Zn1 N1 2.010(3) . ?
Zn2 O1 1.948(3) . ?
Zn2 O1 1.948(3) 5_655 ?
Zn2 N5 2.016(3) 5_655 ?
Zn2 N5 2.016(3) . ?
Zn3 O2 1.943(4) 5_655 ?
Zn3 O2 1.943(4) . ?
Zn3 N8 1.997(3) 3_554 ?
Zn3 N8 1.997(3) 7_655 ?
N4 C12 1.326(5) . ?
N4 C11 1.384(6) . ?
N4 Zn1 2.006(3) 3_554 ?
N1 C3 1.332(5) . ?
N1 C2 1.369(6) . ?
N5 C15 1.324(5) . ?
N5 C13 1.384(6) . ?
C19 C18 1.355(6) . ?
C19 C20 1.402(7) . ?
C19 N7 1.424(5) . ?
C12 N3 1.345(5) . ?
C12 H12A 0.9300 . ?
N6 C15 1.359(5) . ?
N6 C14 1.376(6) . ?
N6 C16 1.420(5) . ?
N8 C24 1.332(5) . ?
N8 C23 1.371(6) . ?
N8 Zn3 1.997(3) 4 ?
C15 H15A 0.9300 . ?
C13 C14 1.337(6) . ?
C13 H13A 0.9300 . ?
N2 C3 1.324(5) . ?
N2 C1 1.386(6) . ?
N2 C4 1.467(5) . ?
N3 C10 1.389(5) . ?
N3 C7 1.445(5) . ?
N7 C24 1.339(5) . ?
N7 C22 1.387(6) . ?
C8 C7 1.343(7) . ?
C8 C9 1.386(6) . ?
C8 H8A 0.9300 . ?
C7 C6 1.348(7) . ?
C24 H24A 0.9300 . ?
C2 C1 1.363(6) . ?
C2 H2A 0.9300 . ?
C11 C10 1.329(6) . ?
C11 H11A 0.9300 . ?
C10 H10A 0.9300 . ?
C1 H1A 0.9300 . ?
C4 C5 1.364(6) . ?
C4 C9 1.371(6) . ?
C17 C16 1.367(6) . ?
C17 C18 1.405(6) . ?
C17 H17A 0.9300 . ?
C3 H3A 0.9300 . ?
C16 C21 1.385(6) . ?
C20 C21 1.369(6) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C5 C6 1.392(7) . ?
C5 H5A 0.9300 . ?
C14 H14A 0.9300 . ?
C9 H9A 0.9300 . ?
C22 C23 1.338(6) . ?
C22 H22A 0.9300 . ?
C6 H6A 0.9300 . ?
C23 H23A 0.9300 . ?
C18 H18A 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
O2 Zn1 O1 113.76(19) . . ?
O2 Zn1 N4 106.89(15) . 4 ?
O1 Zn1 N4 106.13(14) . 4 ?
O2 Zn1 N1 113.79(16) . . ?
O1 Zn1 N1 103.12(13) . . ?
N4 Zn1 N1 113.02(13) 4 . ?
O1 Zn2 O1 116.2(2) . 5_655 ?
O1 Zn2 N5 105.19(14) . 5_655 ?
O1 Zn2 N5 110.61(13) 5_655 5_655 ?
O1 Zn2 N5 110.61(13) . . ?
O1 Zn2 N5 105.19(14) 5_655 . ?
N5 Zn2 N5 108.99(19) 5_655 . ?
O2 Zn3 O2 109.0(3) 5_655 . ?
O2 Zn3 N8 104.22(14) 5_655 3_554 ?
O2 Zn3 N8 110.46(15) . 3_554 ?
O2 Zn3 N8 110.46(15) 5_655 7_655 ?
O2 Zn3 N8 104.22(14) . 7_655 ?
N8 Zn3 N8 118.4(2) 3_554 7_655 ?
C12 N4 C11 106.2(3) . . ?
C12 N4 Zn1 123.2(3) . 3_554 ?
C11 N4 Zn1 130.3(3) . 3_554 ?
C3 N1 C2 106.0(3) . . ?
C3 N1 Zn1 123.9(3) . . ?
C2 N1 Zn1 129.8(3) . . ?
Zn2 O1 Zn1 121.95(17) . . ?
C15 N5 C13 106.8(3) . . ?
C15 N5 Zn2 125.4(3) . . ?
C13 N5 Zn2 127.8(3) . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 N7 121.0(4) . . ?
C20 C19 N7 118.5(3) . . ?
N4 C12 N3 110.8(3) . . ?
N4 C12 H12A 124.6 . . ?
N3 C12 H12A 124.6 . . ?
C15 N6 C14 106.8(3) . . ?
C15 N6 C16 125.3(3) . . ?
C14 N6 C16 127.9(3) . . ?
C24 N8 C23 105.3(3) . . ?
C24 N8 Zn3 120.5(3) . 4 ?
C23 N8 Zn3 133.9(3) . 4 ?
N5 C15 N6 110.0(4) . . ?
N5 C15 H15A 125.0 . . ?
N6 C15 H15A 125.0 . . ?
C14 C13 N5 108.7(4) . . ?
C14 C13 H13A 125.7 . . ?
N5 C13 H13A 125.7 . . ?
C3 N2 C1 109.2(3) . . ?
C3 N2 C4 124.3(3) . . ?
C1 N2 C4 126.5(3) . . ?
C12 N3 C10 106.4(3) . . ?
C12 N3 C7 126.1(3) . . ?
C10 N3 C7 127.4(4) . . ?
C24 N7 C22 106.3(3) . . ?
C24 N7 C19 126.2(3) . . ?
C22 N7 C19 127.4(3) . . ?
C7 C8 C9 122.2(5) . . ?
C7 C8 H8A 118.9 . . ?
C9 C8 H8A 118.9 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 N3 120.4(4) . . ?
C6 C7 N3 119.1(4) . . ?
N7 C24 N8 111.6(3) . . ?
N7 C24 H24A 124.2 . . ?
N8 C24 H24A 124.2 . . ?
C1 C2 N1 110.3(4) . . ?
C1 C2 H2A 124.8 . . ?
N1 C2 H2A 124.8 . . ?
C10 C11 N4 109.1(4) . . ?
C10 C11 H11A 125.4 . . ?
N4 C11 H11A 125.4 . . ?
C11 C10 N3 107.4(4) . . ?
C11 C10 H10A 126.3 . . ?
N3 C10 H10A 126.3 . . ?
C2 C1 N2 104.2(4) . . ?
C2 C1 H1A 127.9 . . ?
N2 C1 H1A 127.9 . . ?
C5 C4 C9 122.3(4) . . ?
C5 C4 N2 118.9(4) . . ?
C9 C4 N2 118.8(4) . . ?
C16 C17 C18 120.9(4) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
N2 C3 N1 110.3(3) . . ?
N2 C3 H3A 124.9 . . ?
N1 C3 H3A 124.9 . . ?
C17 C16 C21 119.5(4) . . ?
C17 C16 N6 121.1(4) . . ?
C21 C16 N6 119.4(4) . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C16 120.2(4) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?
C4 C5 C6 118.7(4) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C13 C14 N6 107.7(4) . . ?
C13 C14 H14A 126.2 . . ?
N6 C14 H14A 126.2 . . ?
C4 C9 C8 116.5(4) . . ?
C4 C9 H9A 121.7 . . ?
C8 C9 H9A 121.7 . . ?
C23 C22 N7 106.7(4) . . ?
C23 C22 H22A 126.6 . . ?
N7 C22 H22A 126.6 . . ?
C7 C6 C5 119.7(5) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C22 C23 N8 110.1(4) . . ?
C22 C23 H23A 125.0 . . ?
N8 C23 H23A 125.0 . . ?
C19 C18 C17 119.0(4) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
Zn1 O2 Zn3 125.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        71.17
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.070
