# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1536032'
_audit_update_record             
;
2017-03-05 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H32 N4 O4 Zn'
_chemical_formula_weight         698.07

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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'
'-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                   24.6587(9)
_cell_length_b                   24.8939(7)
_cell_length_c                   22.3270(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.555(4)
_cell_angle_gamma                90.00
_cell_volume                     12747.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6171
_cell_measurement_theta_min      3.7590
_cell_measurement_theta_max      62.2160

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2896
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8082
_exptl_absorpt_correction_T_max  0.9229
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_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  'SuperNova, Dual, Cu at zero, Atlas'
_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            25463
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         75.08
_reflns_number_total             12663
_reflns_number_gt                5786
_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 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)+(0.1320P)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_number_reflns         12663
_refine_ls_number_parameters     422
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2595
_refine_ls_wR_factor_gt          0.2371
_refine_ls_goodness_of_fit_ref   1.030
_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 0.232212(19) 0.581905(18) 0.22880(2) 0.1038(2) Uani 1 1 d . . .
O1 O 0.27492(16) 0.50714(15) 0.31325(18) 0.1606(12) Uani 1 1 d . . .
O2 O 0.19245(15) 0.54820(14) 0.28056(15) 0.1439(10) Uani 1 1 d . . .
O3 O -0.22485(18) 1.0589(2) 0.1708(2) 0.1951(19) Uani 1 1 d . . .
O4 O -0.3041(2) 1.01343(17) 0.1417(2) 0.1820(14) Uani 1 1 d . . .
N1 N 0.16647(12) 0.63317(12) 0.17766(14) 0.1088(8) Uani 1 1 d . . .
N2 N -0.13364(16) 0.87583(16) -0.01626(15) 0.1250(10) Uani 1 1 d . . .
N3 N -0.20269(13) 0.13203(13) 0.28378(13) 0.1064(8) Uani 1 1 d . . .
N4 N 0.10865(16) 0.36459(15) 0.47476(14) 0.1212(10) Uani 1 1 d . . .
C1 C 0.2266(2) 0.51460(16) 0.3152(2) 0.1208(11) Uani 1 1 d . . .
C2 C 0.20652(15) 0.48369(15) 0.36076(17) 0.1069(9) Uani 1 1 d . . .
C3 C 0.15303(19) 0.4933(2) 0.3658(2) 0.1410(14) Uani 1 1 d . . .
H3 H 0.1272 0.5188 0.3381 0.169 Uiso 1 1 calc R . .
C4 C 0.13697(18) 0.4661(2) 0.4106(2) 0.1387(14) Uani 1 1 d . . .
H4 H 0.1001 0.4730 0.4134 0.166 Uiso 1 1 calc R . .
C5 C 0.17381(17) 0.42939(15) 0.45106(17) 0.1108(10) Uani 1 1 d . . .
C6 C 0.22588(19) 0.42053(16) 0.4459(2) 0.1217(11) Uani 1 1 d . . .
H6 H 0.2514 0.3948 0.4735 0.146 Uiso 1 1 calc R . .
C7 C 0.24323(19) 0.44705(18) 0.4027(2) 0.1345(13) Uani 1 1 d . . .
H7 H 0.2807 0.4403 0.4014 0.161 Uiso 1 1 calc R . .
C8 C 0.15864(19) 0.40308(18) 0.50328(17) 0.1332(14) Uani 1 1 d . . .
H8A H 0.1478 0.4309 0.5286 0.160 Uiso 1 1 calc R . .
H8B H 0.1930 0.3835 0.5327 0.160 Uiso 1 1 calc R . .
C9 C 0.0570(2) 0.3765(2) 0.4716(2) 0.1407(14) Uani 1 1 d . . .
H9 H 0.0495 0.4096 0.4883 0.169 Uiso 1 1 calc R . .
C10 C 0.0116(2) 0.3393(3) 0.4428(3) 0.1558(17) Uani 1 1 d . . .
H10 H -0.0271 0.3482 0.4385 0.187 Uiso 1 1 calc R . .
C11 C 0.0225(3) 0.2906(2) 0.4209(2) 0.1469(18) Uani 1 1 d D . .
C12 C 0.0776(3) 0.2805(2) 0.4285(2) 0.1531(17) Uani 1 1 d . . .
H12 H 0.0875 0.2468 0.4153 0.184 Uiso 1 1 calc R . .
C13 C 0.1185(2) 0.3166(2) 0.4538(2) 0.1447(15) Uani 1 1 d . . .
H13 H 0.1572 0.3082 0.4575 0.174 Uiso 1 1 calc R . .
C14 C -0.0210(2) 0.2462(2) 0.3903(3) 0.1680(18) Uiso 1 1 d D . .
H14 H -0.0073 0.2143 0.3771 0.202 Uiso 1 1 calc R . .
C15 C -0.0708(2) 0.2493(2) 0.3821(3) 0.1678(18) Uiso 1 1 d D . .
H15 H -0.0849 0.2805 0.3961 0.201 Uiso 1 1 calc R . .
C16 C -0.1130(3) 0.2042(2) 0.3497(2) 0.1433(17) Uani 1 1 d D . .
C17 C -0.1682(3) 0.21404(19) 0.3393(2) 0.1487(17) Uani 1 1 d . . .
H17 H -0.1779 0.2468 0.3547 0.178 Uiso 1 1 calc R . .
C18 C -0.21234(19) 0.17890(18) 0.3071(2) 0.1239(11) Uani 1 1 d . . .
H18 H -0.2513 0.1884 0.3013 0.149 Uiso 1 1 calc R . .
C19 C -0.14823(19) 0.1192(2) 0.2948(2) 0.1404(14) Uani 1 1 d . . .
H19 H -0.1396 0.0856 0.2801 0.168 Uiso 1 1 calc R . .
C20 C -0.1017(2) 0.1549(3) 0.3287(2) 0.166(2) Uani 1 1 d . . .
H20 H -0.0625 0.1446 0.3369 0.199 Uiso 1 1 calc R . .
C21 C 0.11243(19) 0.6244(2) 0.1718(3) 0.1454(16) Uani 1 1 d . . .
H21 H 0.1042 0.5926 0.1905 0.174 Uiso 1 1 calc R . .
C22 C 0.0682(2) 0.6573(3) 0.1415(3) 0.170(2) Uani 1 1 d . . .
H22 H 0.0300 0.6482 0.1388 0.204 Uiso 1 1 calc R . .
C23 C 0.0770(3) 0.7040(2) 0.1141(2) 0.157(2) Uani 1 1 d . . .
C24 C 0.1327(3) 0.71329(18) 0.1177(2) 0.1531(18) Uani 1 1 d . . .
H24 H 0.1412 0.7444 0.0981 0.184 Uiso 1 1 calc R . .
C25 C 0.1768(2) 0.67763(17) 0.14962(19) 0.1254(12) Uani 1 1 d . . .
H25 H 0.2153 0.6848 0.1518 0.150 Uiso 1 1 calc R . .
C26 C 0.0389(3) 0.7552(3) 0.0791(3) 0.207(3) Uiso 1 1 d D . .
H26 H 0.0538 0.7856 0.0645 0.248 Uiso 1 1 calc R . .
C27 C -0.0078(3) 0.7502(3) 0.0743(3) 0.207(3) Uiso 1 1 d D . .
H27 H -0.0233 0.7199 0.0882 0.249 Uiso 1 1 calc R . .
C28 C -0.0449(3) 0.8030(3) 0.0397(2) 0.160(2) Uani 1 1 d D . .
C29 C -0.1018(3) 0.7935(2) 0.0328(3) 0.1654(19) Uani 1 1 d . . .
H29 H -0.1107 0.7612 0.0499 0.198 Uiso 1 1 calc R . .
C30 C -0.1455(2) 0.8280(2) 0.0028(3) 0.1575(17) Uani 1 1 d . . .
H30 H -0.1847 0.8183 -0.0046 0.189 Uiso 1 1 calc R . .
C32 C -0.0356(2) 0.8522(3) 0.0172(3) 0.170(2) Uani 1 1 d . . .
H32 H 0.0029 0.8617 0.0213 0.205 Uiso 1 1 calc R . .
C33 C -0.1815(2) 0.91518(19) -0.0474(2) 0.1419(16) Uani 1 1 d . . .
H33A H -0.2156 0.8963 -0.0786 0.170 Uiso 1 1 calc R . .
H33B H -0.1681 0.9425 -0.0711 0.170 Uiso 1 1 calc R . .
C34 C -0.1993(2) 0.94264(18) 0.00402(17) 0.1213(12) Uani 1 1 d . . .
C35 C -0.2507(2) 0.93115(18) 0.0105(2) 0.1348(13) Uani 1 1 d . . .
H35 H -0.2748 0.9038 -0.0155 0.162 Uiso 1 1 calc R . .
C36 C -0.2686(2) 0.95733(18) 0.0527(2) 0.1395(14) Uani 1 1 d . . .
H36 H -0.3054 0.9493 0.0552 0.167 Uiso 1 1 calc R . .
C38 C -0.2341(2) 0.9948(2) 0.09120(19) 0.1307(14) Uani 1 1 d . . .
C39 C -0.1828(2) 1.0085(2) 0.0857(2) 0.167(2) Uani 1 1 d . . .
H39 H -0.1595 1.0362 0.1121 0.200 Uiso 1 1 calc R . .
C40 C -0.1641(2) 0.9821(2) 0.0418(3) 0.1609(19) Uani 1 1 d . . .
H40 H -0.1281 0.9912 0.0380 0.193 Uiso 1 1 calc R . .
C37 C -0.2545(3) 1.0249(2) 0.1434(3) 0.1455(16) Uani 1 1 d . . .
C31 C -0.0795(3) 0.8877(2) -0.0106(3) 0.1577(17) Uani 1 1 d . . .
H31 H -0.0715 0.9211 -0.0260 0.189 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
Zn1 O2 1.958(3) . ?
Zn1 O3 2.033(4) 3_545 ?
Zn1 N3 2.048(3) 3 ?
Zn1 N1 2.049(3) . ?
Zn1 C37 2.493(6) 3_545 ?
Zn1 C1 2.598(4) . ?
O1 C1 1.223(5) . ?
O2 C1 1.236(5) . ?
O3 C37 1.140(6) . ?
O3 Zn1 2.033(4) 3_455 ?
O4 C37 1.240(6) . ?
N1 C21 1.309(5) . ?
N1 C25 1.341(5) . ?
N2 C31 1.326(6) . ?
N2 C30 1.332(6) . ?
N2 C33 1.495(5) . ?
N3 C19 1.313(5) . ?
N3 C18 1.335(5) . ?
N3 Zn1 2.048(3) 3_445 ?
N4 C9 1.284(5) . ?
N4 C13 1.337(6) . ?
N4 C8 1.506(5) . ?
C1 C2 1.496(5) . ?
C2 C7 1.380(5) . ?
C2 C3 1.385(5) . ?
C3 C4 1.380(6) . ?
C4 C5 1.370(5) . ?
C5 C6 1.349(5) . ?
C5 C8 1.499(5) . ?
C6 C7 1.361(6) . ?
C9 C10 1.412(6) . ?
C10 C11 1.370(7) . ?
C11 C12 1.329(7) . ?
C11 C14 1.518(6) . ?
C12 C13 1.314(6) . ?
C14 C15 1.177(6) . ?
C15 C16 1.520(6) . ?
C16 C17 1.315(7) . ?
C16 C20 1.379(8) . ?
C17 C18 1.376(6) . ?
C19 C20 1.430(6) . ?
C21 C22 1.332(6) . ?
C22 C23 1.366(8) . ?
C23 C24 1.367(8) . ?
C23 C26 1.606(8) . ?
C24 C25 1.381(6) . ?
C26 C27 1.123(7) . ?
C27 C28 1.624(7) . ?
C28 C32 1.374(8) . ?
C28 C29 1.374(8) . ?
C29 C30 1.349(6) . ?
C32 C31 1.359(7) . ?
C33 C34 1.532(5) . ?
C34 C35 1.358(6) . ?
C34 C40 1.376(6) . ?
C35 C36 1.347(6) . ?
C36 C38 1.340(6) . ?
C38 C39 1.359(7) . ?
C38 C37 1.614(7) . ?
C39 C40 1.392(6) . ?
C37 Zn1 2.493(6) 3_455 ?

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 O3 138.3(2) . 3_545 ?
O2 Zn1 N3 111.07(12) . 3 ?
O3 Zn1 N3 94.39(16) 3_545 3 ?
O2 Zn1 N1 97.50(14) . . ?
O3 Zn1 N1 108.11(15) 3_545 . ?
N3 Zn1 N1 103.88(13) 3 . ?
O2 Zn1 C37 116.23(19) . 3_545 ?
O3 Zn1 C37 26.78(17) 3_545 3_545 ?
N3 Zn1 C37 120.76(17) 3 3_545 ?
N1 Zn1 C37 103.17(14) . 3_545 ?
O2 Zn1 C1 27.13(13) . . ?
O3 Zn1 C1 118.31(18) 3_545 . ?
N3 Zn1 C1 101.06(12) 3 . ?
N1 Zn1 C1 124.62(14) . . ?
C37 Zn1 C1 104.99(17) 3_545 . ?
C1 O2 Zn1 106.6(3) . . ?
C37 O3 Zn1 99.7(5) . 3_455 ?
C21 N1 C25 116.8(4) . . ?
C21 N1 Zn1 121.3(3) . . ?
C25 N1 Zn1 121.8(3) . . ?
C31 N2 C30 119.9(4) . . ?
C31 N2 C33 119.6(5) . . ?
C30 N2 C33 120.4(4) . . ?
C19 N3 C18 117.2(4) . . ?
C19 N3 Zn1 119.1(3) . 3_445 ?
C18 N3 Zn1 123.6(3) . 3_445 ?
C9 N4 C13 119.4(4) . . ?
C9 N4 C8 121.2(4) . . ?
C13 N4 C8 119.4(4) . . ?
O1 C1 O2 121.9(4) . . ?
O1 C1 C2 121.1(4) . . ?
O2 C1 C2 117.0(4) . . ?
O1 C1 Zn1 75.7(3) . . ?
O2 C1 Zn1 46.2(2) . . ?
C2 C1 Zn1 163.3(3) . . ?
C7 C2 C3 117.8(4) . . ?
C7 C2 C1 120.2(4) . . ?
C3 C2 C1 121.9(4) . . ?
C4 C3 C2 120.6(4) . . ?
C5 C4 C3 120.5(4) . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 C8 120.8(4) . . ?
C4 C5 C8 120.7(4) . . ?
C5 C6 C7 122.6(4) . . ?
C6 C7 C2 120.2(4) . . ?
C5 C8 N4 110.4(3) . . ?
N4 C9 C10 118.6(5) . . ?
C11 C10 C9 121.0(5) . . ?
C12 C11 C10 116.6(5) . . ?
C12 C11 C14 116.1(6) . . ?
C10 C11 C14 127.4(6) . . ?
C13 C12 C11 120.8(6) . . ?
C12 C13 N4 123.5(5) . . ?
C15 C14 C11 123.2(6) . . ?
C14 C15 C16 121.3(6) . . ?
C17 C16 C20 115.5(4) . . ?
C17 C16 C15 115.5(6) . . ?
C20 C16 C15 129.0(6) . . ?
C16 C17 C18 122.9(5) . . ?
N3 C18 C17 122.6(4) . . ?
N3 C19 C20 120.9(5) . . ?
C16 C20 C19 120.7(5) . . ?
N1 C21 C22 124.1(5) . . ?
C21 C22 C23 121.1(5) . . ?
C22 C23 C24 116.0(5) . . ?
C22 C23 C26 137.1(7) . . ?
C24 C23 C26 106.9(6) . . ?
C23 C24 C25 120.3(5) . . ?
N1 C25 C24 121.6(5) . . ?
C27 C26 C23 110.9(8) . . ?
C26 C27 C28 109.6(8) . . ?
C32 C28 C29 114.4(5) . . ?
C32 C28 C27 138.9(7) . . ?
C29 C28 C27 106.7(6) . . ?
C30 C29 C28 122.9(6) . . ?
N2 C30 C29 119.9(5) . . ?
C31 C32 C28 122.3(6) . . ?
N2 C33 C34 109.8(3) . . ?
C35 C34 C40 119.2(4) . . ?
C35 C34 C33 121.4(4) . . ?
C40 C34 C33 119.2(5) . . ?
C36 C35 C34 122.1(5) . . ?
C38 C36 C35 119.4(5) . . ?
C36 C38 C39 120.6(4) . . ?
C36 C38 C37 119.5(5) . . ?
C39 C38 C37 119.8(5) . . ?
C38 C39 C40 120.4(5) . . ?
C34 C40 C39 118.1(5) . . ?
O3 C37 O4 128.2(6) . . ?
O3 C37 C38 115.0(6) . . ?
O4 C37 C38 115.8(5) . . ?
O3 C37 Zn1 53.5(4) . 3_455 ?
O4 C37 Zn1 75.6(3) . 3_455 ?
C38 C37 Zn1 168.5(4) . 3_455 ?
N2 C31 C32 120.3(6) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        75.08
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.057
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
1 -0.002 0.002 -0.010 7376.2 1584.6
_platon_squeeze_details          
; ?
;
