# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 972578'
_audit_update_record             
;
2013-11-18 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H36 N6 O7 Zn4'
_chemical_formula_weight         998.33

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

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P -3 c 1'

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

_cell_length_a                   14.5525(3)
_cell_length_b                   14.5525(3)
_cell_length_c                   24.7573(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4540.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4818
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      24.108

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2024
_exptl_absorpt_coefficient_mu    2.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  0.652
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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       'κ-geometry diffractometr'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8072
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         23.25
_reflns_number_total             2174
_reflns_number_gt                1904
_reflns_threshold_expression     I>2σ(I)


_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    
;
DIAMOND v3.1 (Brandenburg, 1999)
Ortep-3 for Windows, L.J.Farrugia (1997) J.Appl.Cryst. 30, 565,
ORTEP III (Burnett, Johnson, 1996)
;
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008),
;

_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 > 2σ(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)+(0.0348P)²+10.2267P] where P=(Fo²+2Fc²)/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         2174
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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
C1 C 0.2908(5) 0.4369(4) 0.2881(2) 0.0649(14) Uani 1 1 d . . .
C2 C 0.2692(5) 0.3350(5) 0.3140(3) 0.0741(16) Uani 1 1 d . . .
C3 C 0.3446(5) 0.3218(5) 0.3408(2) 0.0736(16) Uani 1 1 d . . .
H3 H 0.4145 0.3807 0.3440 0.088 Uiso 1 1 calc R . .
C4 C 0.3223(7) 0.2265(6) 0.3632(3) 0.092(2) Uani 1 1 d . . .
H4 H 0.3757 0.2197 0.3819 0.110 Uiso 1 1 calc R . .
C5 C 0.2251(10) 0.1440(8) 0.3582(6) 0.173(5) Uani 1 1 d . . .
H5 H 0.2099 0.0775 0.3728 0.207 Uiso 1 1 calc R . .
C6 C 0.1447(9) 0.1520(7) 0.3322(8) 0.241(9) Uani 1 1 d . . .
H6 H 0.0748 0.0929 0.3300 0.289 Uiso 1 1 calc R . .
C7 C 0.1699(7) 0.2502(6) 0.3093(5) 0.172(5) Uani 1 1 d . . .
H7 H 0.1170 0.2573 0.2905 0.206 Uiso 1 1 calc R . .
C8 C 0.1091(6) 0.4840(7) 0.1253(4) 0.095(2) Uani 1 1 d . . .
C9 C 0.0316(6) 0.4068(6) 0.0866(3) 0.0842(19) Uani 1 1 d . . .
C10 C -0.0536(7) 0.3166(9) 0.1051(3) 0.140(4) Uani 1 1 d . . .
H10 H -0.0660 0.3059 0.1429 0.168 Uiso 1 1 calc R . .
C11 C -0.1218(7) 0.2412(9) 0.0698(4) 0.179(5) Uani 1 1 d . . .
H11 H -0.1809 0.1783 0.0833 0.214 Uiso 1 1 calc R . .
C12 C -0.1062(7) 0.2549(9) 0.0156(3) 0.141(4) Uani 1 1 d . . .
H12 H -0.1541 0.2018 -0.0085 0.169 Uiso 1 1 calc R . .
C13 C -0.0223(9) 0.3444(8) -0.0037(3) 0.136(3) Uani 1 1 d . . .
H13 H -0.0103 0.3545 -0.0415 0.164 Uiso 1 1 calc R . .
C14 C 0.0460(7) 0.4213(7) 0.0324(3) 0.120(3) Uani 1 1 d . . .
H14 H 0.1038 0.4853 0.0190 0.145 Uiso 1 1 calc R . .
O1 O 0.2118(3) 0.4453(3) 0.27406(17) 0.0786(11) Uani 1 1 d . . .
O2 O 0.1880(6) 0.5648(6) 0.1046(2) 0.144(2) Uani 1 1 d . . .
O3 O 0.3333 0.6667 0.2109(2) 0.0661(16) Uani 1 3 d S . .
N1 N 0.3890(4) 0.5115(4) 0.27940(17) 0.0655(12) Uani 1 1 d . . .
H1 H 0.4374 0.5019 0.2956 0.079 Uiso 1 1 calc R . .
N2 N 0.1014(4) 0.4760(4) 0.1754(2) 0.0767(14) Uani 1 1 d . . .
H2 H 0.0400 0.4232 0.1861 0.092 Uiso 1 1 calc R . .
Zn1 Zn 0.19582(5) 0.55486(5) 0.23615(3) 0.0662(3) Uani 1 1 d . . .
Zn2 Zn 0.3333 0.6667 0.13240(5) 0.0914(5) Uani 1 3 d S . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 O1 1.264(7) . ?
C1 N1 1.310(7) . ?
C1 C2 1.498(8) . ?
C2 C7 1.357(10) . ?
C2 C3 1.375(8) . ?
C3 C4 1.374(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.327(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(12) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N2 1.245(9) . ?
C8 O2 1.270(9) . ?
C8 C9 1.477(9) . ?
C9 C10 1.357(11) . ?
C9 C14 1.359(10) . ?
C10 C11 1.365(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.357(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.351(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(11) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O1 Zn1 1.961(4) . ?
O2 Zn2 2.003(7) . ?
O3 Zn2 1.942(6) . ?
O3 Zn1 1.946(2) 3_565 ?
O3 Zn1 1.946(2) . ?
O3 Zn1 1.946(2) 2_665 ?
N1 Zn1 1.955(4) 2_665 ?
N1 H1 0.8800 . ?
N2 Zn1 1.973(5) . ?
N2 H2 0.8800 . ?
Zn1 N1 1.955(4) 3_565 ?
Zn2 O2 2.003(7) 3_565 ?
Zn2 O2 2.003(7) 2_665 ?

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 C1 N1 122.9(5) . . ?
O1 C1 C2 117.6(5) . . ?
N1 C1 C2 119.5(5) . . ?
C7 C2 C3 118.4(7) . . ?
C7 C2 C1 117.7(7) . . ?
C3 C2 C1 123.9(6) . . ?
C4 C3 C2 122.3(7) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C5 C4 C3 118.9(8) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.9(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 118.0(10) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C2 C7 C6 120.6(10) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N2 C8 O2 119.1(7) . . ?
N2 C8 C9 125.1(9) . . ?
O2 C8 C9 115.8(8) . . ?
C10 C9 C14 118.6(7) . . ?
C10 C9 C8 119.9(7) . . ?
C14 C9 C8 121.5(8) . . ?
C9 C10 C11 120.5(8) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.9(9) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.8(8) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.0(8) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C9 C14 C13 121.3(8) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C1 O1 Zn1 133.9(4) . . ?
C8 O2 Zn2 132.7(5) . . ?
Zn2 O3 Zn1 108.77(16) . 3_565 ?
Zn2 O3 Zn1 108.77(16) . . ?
Zn1 O3 Zn1 110.16(16) 3_565 . ?
Zn2 O3 Zn1 108.77(16) . 2_665 ?
Zn1 O3 Zn1 110.16(16) 3_565 2_665 ?
Zn1 O3 Zn1 110.16(16) . 2_665 ?
C1 N1 Zn1 130.2(4) . 2_665 ?
C1 N1 H1 114.9 . . ?
Zn1 N1 H1 114.9 2_665 . ?
C8 N2 Zn1 134.6(6) . . ?
C8 N2 H2 112.7 . . ?
Zn1 N2 H2 112.7 . . ?
O3 Zn1 N1 112.00(16) . 3_565 ?
O3 Zn1 O1 110.08(14) . . ?
N1 Zn1 O1 112.87(19) 3_565 . ?
O3 Zn1 N2 111.5(2) . . ?
N1 Zn1 N2 107.11(19) 3_565 . ?
O1 Zn1 N2 102.9(2) . . ?
O3 Zn2 O2 110.12(19) . 3_565 ?
O3 Zn2 O2 110.1(2) . . ?
O2 Zn2 O2 108.8(2) 3_565 . ?
O3 Zn2 O2 110.12(19) . 2_665 ?
O2 Zn2 O2 108.8(2) 3_565 2_665 ?
O2 Zn2 O2 108.8(2) . 2_665 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.055
