# 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_CP
_database_code_depnum_ccdc_archive 'CCDC 1004144'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 N4 O4 Zn'
_chemical_formula_weight         567.89

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   15.1755(11)
_cell_length_b                   22.2665(17)
_cell_length_c                   8.1466(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.2820(10)
_cell_angle_gamma                90.00
_cell_volume                     2582.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7561
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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 CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8186
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.04
_reflns_number_total             3854
_reflns_number_gt                3050
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_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)+(0.0573P)²+2.1198P] 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   0.49(3)
_refine_ls_number_reflns         3854
_refine_ls_number_parameters     341
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.002
_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 0.24656(19) 0.13475(2) -0.2924(3) 0.04508(19) Uani 1 1 d . . .
C1 C 0.4237(7) 0.0649(6) -0.2903(13) 0.055(3) Uani 1 1 d . . .
H1 H 0.4514 0.1024 -0.2871 0.066 Uiso 1 1 calc R . .
C2 C 0.4707(10) 0.0165(8) -0.2938(16) 0.079(4) Uani 1 1 d . . .
H2 H 0.5328 0.0201 -0.2878 0.095 Uiso 1 1 calc R . .
C3 C 0.4318(12) -0.0404(7) -0.3059(13) 0.097(5) Uani 1 1 d . . .
H3 H 0.4647 -0.0743 -0.3181 0.116 Uiso 1 1 calc R . .
C4 C 0.3376(10) -0.0449(6) -0.2989(18) 0.075(4) Uani 1 1 d . . .
H4 H 0.3076 -0.0813 -0.2991 0.089 Uiso 1 1 calc R . .
C5 C 0.2977(6) 0.0086(5) -0.2921(11) 0.038(3) Uani 1 1 d . . .
C6 C 0.1999(8) 0.0064(4) -0.2905(13) 0.048(3) Uani 1 1 d . . .
C7 C 0.1443(8) -0.0441(4) -0.2881(14) 0.051(3) Uani 1 1 d . . .
H7 H 0.1702 -0.0819 -0.2879 0.061 Uiso 1 1 calc R . .
C8 C 0.0591(7) -0.0412(5) -0.2863(17) 0.076(4) Uani 1 1 d . . .
H8 H 0.0252 -0.0762 -0.2892 0.091 Uiso 1 1 calc R . .
C9 C 0.0194(9) 0.0134(6) -0.2800(17) 0.072(4) Uani 1 1 d . . .
H9 H -0.0402 0.0172 -0.2729 0.087 Uiso 1 1 calc R . .
C10 C 0.0764(10) 0.0651(6) -0.2853(19) 0.077(4) Uani 1 1 d . . .
H10 H 0.0513 0.1030 -0.2825 0.093 Uiso 1 1 calc R . .
C11 C 0.1702(16) 0.6302(8) 0.102(3) 0.107(7) Uani 1 1 d . . .
H11 H 0.1185 0.6497 0.0238 0.129 Uiso 1 1 calc R . .
C12 C 0.2404(19) 0.6650(3) 0.201(3) 0.115(4) Uani 1 1 d . . .
H12 H 0.2343 0.7065 0.2015 0.138 Uiso 1 1 calc R . .
C13 C 0.3242(16) 0.6363(6) 0.306(3) 0.088(6) Uani 1 1 d . . .
H13 H 0.3771 0.6585 0.3694 0.106 Uiso 1 1 calc R . .
C14 C 0.3251(11) 0.5734(7) 0.313(2) 0.078(4) Uani 1 1 d . . .
H14 H 0.3766 0.5526 0.3870 0.094 Uiso 1 1 calc R . .
C15 C 0.2483(12) 0.5439(2) 0.207(2) 0.0524(12) Uani 1 1 d . . .
C16 C 0.2457(12) 0.4771(2) 0.208(2) 0.0537(12) Uani 1 1 d . . .
C17 C 0.3159(9) 0.4481(5) 0.3276(15) 0.057(3) Uani 1 1 d . . .
H17 H 0.3649 0.4681 0.4113 0.068 Uiso 1 1 calc R . .
C18 C 0.3103(15) 0.3868(10) 0.317(3) 0.113(6) Uani 1 1 d . . .
H18 H 0.3568 0.3649 0.4009 0.135 Uiso 1 1 calc R . .
C19 C 0.242(2) 0.3555(3) 0.195(5) 0.105(4) Uani 1 1 d . . .
H19 H 0.2442 0.3139 0.1882 0.126 Uiso 1 1 calc R . .
C20 C 0.1709(14) 0.3868(7) 0.083(3) 0.096(5) Uani 1 1 d . . .
H20 H 0.1211 0.3663 0.0033 0.115 Uiso 1 1 calc R . .
C21 C 0.3432(12) 0.1876(6) -0.0194(14) 0.081(5) Uani 1 1 d . . .
C22 C 0.4006(4) 0.2120(3) 0.1601(6) 0.085(4) Uani 1 1 d G . .
C23 C 0.3706(4) 0.2073(3) 0.3026(8) 0.105(4) Uani 1 1 d G . .
H23 H 0.3133 0.1893 0.2893 0.126 Uiso 1 1 calc R . .
C24 C 0.4264(5) 0.2294(3) 0.4649(7) 0.067(2) Uani 1 1 d G . .
H24 H 0.4063 0.2262 0.5602 0.081 Uiso 1 1 calc R . .
C25 C 0.5121(5) 0.2563(3) 0.4847(6) 0.067(2) Uani 1 1 d G . .
C26 C 0.5421(4) 0.2611(2) 0.3422(8) 0.069(2) Uani 1 1 d G . .
H26 H 0.5994 0.2791 0.3555 0.083 Uiso 1 1 calc R . .
C27 C 0.4863(4) 0.2389(2) 0.1799(6) 0.0647(19) Uani 1 1 d G . .
H27 H 0.5064 0.2421 0.0846 0.078 Uiso 1 1 calc R . .
C28 C 0.5861(10) 0.2845(5) 0.6455(16) 0.108(4) Uani 1 1 d DU . .
H28 H 0.6385 0.3033 0.6347 0.130 Uiso 1 1 calc R . .
C29 C 0.5761(9) 0.2822(5) 0.7865(15) 0.103(4) Uani 1 1 d D . .
H29 H 0.5243 0.2627 0.7976 0.123 Uiso 1 1 calc R . .
C30 C 0.6480(11) 0.3112(5) 0.945(2) 0.092(6) Uani 1 1 d . . .
N1 N 0.3319(7) 0.0609(4) -0.2914(10) 0.042(2) Uani 1 1 d . . .
N2 N 0.1577(7) 0.0621(4) -0.2933(12) 0.049(2) Uani 1 1 d . . .
N3 N 0.1674(9) 0.5726(5) 0.1046(16) 0.071(3) Uani 1 1 d . . .
N4 N 0.1700(9) 0.4486(6) 0.0844(19) 0.091(4) Uani 1 1 d . . .
O1 O 0.2688(8) 0.1606(4) -0.0358(11) 0.075(3) Uani 1 1 d . . .
O2 O 0.3676(6) 0.1930(4) -0.1486(14) 0.081(3) Uani 1 1 d . . .
O3 O 0.7209(8) 0.3373(4) 0.9484(13) 0.081(3) Uani 1 1 d . . .
O4 O 0.6242(8) 0.3084(5) 1.0767(14) 0.096(4) 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 O1 2.080(8) . ?
Zn1 N1 2.091(10) . ?
Zn1 O3 2.104(10) 4_453 ?
Zn1 N2 2.105(10) . ?
Zn1 O4 2.194(11) 4_453 ?
Zn1 O2 2.222(10) . ?
Zn1 C30 2.458(13) 4_453 ?
Zn1 C21 2.495(12) . ?
C1 C2 1.300(18) . ?
C1 N1 1.393(13) . ?
C2 C3 1.386(19) . ?
C3 C4 1.45(2) . ?
C4 C5 1.346(16) . ?
C5 N1 1.273(14) . ?
C5 C6 1.490(7) . ?
C6 N2 1.392(14) . ?
C6 C7 1.410(14) . ?
C7 C8 1.300(14) . ?
C8 C9 1.365(15) . ?
C9 C10 1.450(17) . ?
C10 N2 1.259(15) . ?
C11 N3 1.283(19) . ?
C11 C12 1.34(3) . ?
C12 C13 1.42(3) . ?
C13 C14 1.400(17) . ?
C14 C15 1.35(2) . ?
C15 N3 1.380(18) . ?
C15 C16 1.489(6) . ?
C16 C17 1.333(19) . ?
C16 N4 1.39(2) . ?
C17 C18 1.37(2) . ?
C18 C19 1.36(3) . ?
C19 C20 1.34(3) . ?
C20 N4 1.376(17) . ?
C21 O2 1.237(16) . ?
C21 O1 1.246(19) . ?
C21 C22 1.519(12) . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 C24 1.3900 . ?
C24 C25 1.3900 . ?
C25 C26 1.3900 . ?
C25 C28 1.533(10) . ?
C26 C27 1.3900 . ?
C28 C29 1.210(14) . ?
C29 C30 1.515(16) . ?
C30 O3 1.242(17) . ?
C30 O4 1.246(19) . ?
C30 Zn1 2.458(13) 4_556 ?
O3 Zn1 2.104(10) 4_556 ?
O4 Zn1 2.194(11) 4_556 ?

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
O1 Zn1 N1 109.2(4) . . ?
O1 Zn1 O3 146.70(17) . 4_453 ?
N1 Zn1 O3 97.8(4) . 4_453 ?
O1 Zn1 N2 95.5(4) . . ?
N1 Zn1 N2 77.93(16) . . ?
O3 Zn1 N2 109.2(4) 4_453 . ?
O1 Zn1 O4 98.3(4) . 4_453 ?
N1 Zn1 O4 150.9(4) . 4_453 ?
O3 Zn1 O4 60.7(4) 4_453 4_453 ?
N2 Zn1 O4 90.5(4) . 4_453 ?
O1 Zn1 O2 59.5(4) . . ?
N1 Zn1 O2 93.4(4) . . ?
O3 Zn1 O2 100.9(4) 4_453 . ?
N2 Zn1 O2 149.5(4) . . ?
O4 Zn1 O2 108.98(19) 4_453 . ?
O1 Zn1 C30 125.2(5) . 4_453 ?
N1 Zn1 C30 125.3(5) . 4_453 ?
O3 Zn1 C30 30.3(5) 4_453 4_453 ?
N2 Zn1 C30 100.2(4) . 4_453 ?
O4 Zn1 C30 30.4(5) 4_453 4_453 ?
O2 Zn1 C30 108.4(4) . 4_453 ?
O1 Zn1 C21 29.9(4) . . ?
N1 Zn1 C21 101.3(4) . . ?
O3 Zn1 C21 127.0(5) 4_453 . ?
N2 Zn1 C21 122.9(5) . . ?
O4 Zn1 C21 107.3(4) 4_453 . ?
O2 Zn1 C21 29.7(4) . . ?
C30 Zn1 C21 122.5(2) 4_453 . ?
C2 C1 N1 120.2(13) . . ?
C1 C2 C3 122.4(14) . . ?
C2 C3 C4 117.4(12) . . ?
C5 C4 C3 113.7(12) . . ?
N1 C5 C4 128.5(11) . . ?
N1 C5 C6 115.8(11) . . ?
C4 C5 C6 115.7(13) . . ?
N2 C6 C7 115.8(10) . . ?
N2 C6 C5 115.1(11) . . ?
C7 C6 C5 129.1(12) . . ?
C8 C7 C6 124.3(10) . . ?
C7 C8 C9 119.9(10) . . ?
C8 C9 C10 115.4(11) . . ?
N2 C10 C9 124.4(12) . . ?
N3 C11 C12 126.4(18) . . ?
C11 C12 C13 117.7(7) . . ?
C14 C13 C12 117.9(17) . . ?
C15 C14 C13 117.8(17) . . ?
C14 C15 N3 123.3(5) . . ?
C14 C15 C16 120.0(15) . . ?
N3 C15 C16 116.5(14) . . ?
C17 C16 N4 124.0(5) . . ?
C17 C16 C15 118.2(15) . . ?
N4 C16 C15 117.9(14) . . ?
C16 C17 C18 114.9(14) . . ?
C19 C18 C17 124.9(18) . . ?
C20 C19 C18 117.5(8) . . ?
C19 C20 N4 121.6(17) . . ?
O2 C21 O1 118.9(11) . . ?
O2 C21 C22 123.0(16) . . ?
O1 C21 C22 118.2(13) . . ?
O2 C21 Zn1 62.8(7) . . ?
O1 C21 Zn1 56.3(6) . . ?
C22 C21 Zn1 172.1(10) . . ?
C23 C22 C27 120.0 . . ?
C23 C22 C21 122.1(9) . . ?
C27 C22 C21 117.9(9) . . ?
C24 C23 C22 120.0 . . ?
C23 C24 C25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 C28 109.1(7) . . ?
C24 C25 C28 130.9(7) . . ?
C27 C26 C25 120.0 . . ?
C26 C27 C22 120.0 . . ?
C29 C28 C25 119.9(13) . . ?
C28 C29 C30 120.1(15) . . ?
O3 C30 O4 121.7(14) . . ?
O3 C30 C29 126.2(17) . . ?
O4 C30 C29 112.1(15) . . ?
O3 C30 Zn1 58.9(7) . 4_556 ?
O4 C30 Zn1 63.0(8) . 4_556 ?
C29 C30 Zn1 172.3(12) . 4_556 ?
C5 N1 C1 117.6(10) . . ?
C5 N1 Zn1 117.9(7) . . ?
C1 N1 Zn1 124.5(8) . . ?
C10 N2 C6 120.0(10) . . ?
C10 N2 Zn1 126.6(9) . . ?
C6 N2 Zn1 113.2(7) . . ?
C11 N3 C15 116.4(16) . . ?
C20 N4 C16 116.9(14) . . ?
C21 O1 Zn1 93.8(7) . . ?
C21 O2 Zn1 87.5(9) . . ?
C30 O3 Zn1 90.8(10) . 4_556 ?
C30 O4 Zn1 86.6(9) . 4_556 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.070
