# 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_NNU-27
_database_code_depnum_ccdc_archive 'CCDC 995215'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2015-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C74 H54 N2 Na2 O10 Zn'
_chemical_formula_weight         1242.54

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           133
_space_group_name_H-M_alt        'P 42/n b c'
_space_group_name_Hall           '-P 4ac 2b'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   30.871(3)
_cell_length_b                   30.871(3)
_cell_length_c                   10.6581(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10157(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4182
_cell_measurement_theta_min      2.412
_cell_measurement_theta_max      19.744

_exptl_crystal_description       needle-like
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not mesaured'
_exptl_crystal_density_diffrn    0.813
_exptl_crystal_F_000             2576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42799
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.322
_diffrn_reflns_theta_max         23.271
_diffrn_reflns_theta_full        23.271
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3651
_reflns_number_gt                2010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-2014/7
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1263P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3651
_refine_ls_number_parameters     233
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.2018
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.7500 0.2500 0.7500 0.0482(3) Uani 1 4 d S T P . .
Na1 Na 0.7500 0.17819(9) 1.0000 0.1002(9) Uani 1 2 d S T P . .
O1 O 0.79432(9) 0.22425(8) 0.8625(2) 0.0605(7) Uani 1 1 d . U . . .
O2 O 0.83056(9) 0.21519(9) 0.6841(3) 0.0862(10) Uani 1 1 d . . . . .
O3 O 0.7856(4) 0.1115(4) 0.9238(14) 0.213(6) Uani 0.5 1 d D U P . .
N1 N 0.7610(10) 0.0476(6) 0.873(2) 0.395(13) Uani 0.5 1 d D U P . .
C1 C 0.82717(14) 0.21055(12) 0.7992(4) 0.0630(11) Uani 1 1 d . . . . .
C2 C 0.9847(2) 0.0939(2) 1.5172(7) 0.145(3) Uani 1 1 d . . . . .
H2A H 0.9656 0.1116 1.5666 0.174 Uiso 1 1 d R U . . .
C3 C 0.86172(12) 0.18796(12) 0.8703(4) 0.0595(10) Uani 1 1 d . . . . .
C4 C 0.86437(13) 0.19071(13) 0.9988(4) 0.0692(11) Uani 1 1 d . . . . .
H4A H 0.8438 0.2079 1.0444 0.083 Uiso 1 1 d R U . . .
C5 C 0.89133(15) 0.16311(15) 0.8056(4) 0.0853(14) Uani 1 1 d . . . . .
H5A H 0.8904 0.1618 0.7157 0.102 Uiso 1 1 d R U . . .
C6 C 0.92207(16) 0.14028(17) 0.8700(5) 0.1066(18) Uani 1 1 d . . . . .
H6A H 0.9428 0.1230 0.8251 0.128 Uiso 1 1 d R U . . .
C7 C 0.89519(15) 0.16828(15) 1.0637(5) 0.0814(13) Uani 1 1 d . . . . .
H7A H 0.8972 0.1704 1.1534 0.098 Uiso 1 1 d R U . . .
C8 C 0.92502(16) 0.14248(15) 0.9996(5) 0.0925(15) Uani 1 1 d . . . . .
C9 C 0.95710(18) 0.11771(18) 1.0661(5) 0.1094(18) Uani 1 1 d . . . . .
C10 C 0.98216(17) 0.09554(18) 1.1217(5) 0.1119(18) Uani 1 1 d . . . . .
C11 C 1.01162(17) 0.06783(17) 1.1877(6) 0.1021(17) Uani 1 1 d . . . . .
C12 C 1.01162(17) 0.06766(18) 1.3194(6) 0.1027(17) Uani 1 1 d . . . . .
C13 C 1.04073(18) 0.03903(19) 1.3814(6) 0.1019(17) Uani 1 1 d . . . . .
C14 C 1.0403(2) 0.0393(2) 1.5142(7) 0.129(2) Uani 1 1 d . . . . .
H14A H 1.0580 0.0188 1.5583 0.154 Uiso 1 1 d R U . . .
C15 C 0.9837(2) 0.0945(2) 1.3919(7) 0.122(2) Uani 1 1 d . . . . .
H15A H 0.9639 0.1134 1.3491 0.147 Uiso 1 1 d R U . . .
C16 C 1.0135(3) 0.0652(2) 1.5793(7) 0.152(3) Uani 1 1 d . . . . .
H16A H 1.0161 0.0656 1.6691 0.182 Uiso 1 1 d R U . . .
C17 C 0.7963(10) 0.0747(7) 0.899(3) 0.313(11) Uani 0.5 1 d D U P . .
H17 H 0.8250 0.0654 0.8976 0.375 Uiso 0.5 1 calc R U P . .
C18 C 0.7250(11) 0.0396(10) 0.969(3) 0.426(18) Uani 0.5 1 d D U P . .
H18A H 0.7331 0.0152 1.0214 0.511 Uiso 0.5 1 calc R U P . .
H18B H 0.6987 0.0318 0.9247 0.511 Uiso 0.5 1 calc R U P . .
C19 C 0.7157(18) 0.0804(10) 1.056(4) 0.42(2) Uani 0.5 1 d D U P . .
H19A H 0.6929 0.0736 1.1136 0.628 Uiso 0.5 1 calc R U P . .
H19B H 0.7415 0.0879 1.1010 0.628 Uiso 0.5 1 calc R U P . .
H19C H 0.7070 0.1045 1.0043 0.628 Uiso 0.5 1 calc R U P . .
C20 C 0.7492(14) 0.0134(10) 0.790(2) 0.441(18) Uani 0.5 1 d D U P . .
H20A H 0.7184 0.0090 0.8031 0.529 Uiso 0.5 1 calc R U P . .
H20B H 0.7633 -0.0122 0.8232 0.529 Uiso 0.5 1 calc R U P . .
C21 C 0.7556(11) 0.0106(10) 0.645(2) 0.430(19) Uani 0.5 1 d D U P . .
H21A H 0.7444 -0.0165 0.6154 0.645 Uiso 0.5 1 calc R U P . .
H21B H 0.7404 0.0340 0.6057 0.645 Uiso 0.5 1 calc R U P . .
H21C H 0.7859 0.0125 0.6260 0.645 Uiso 0.5 1 calc R U P . .


_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 1.985(2) 11_667 ?
Zn1 O1 1.985(2) 12_657 ?
Zn1 O1 1.985(2) 2_655 ?
Zn1 O1 1.986(2) . ?
Zn1 Na1 3.4661(19) . ?
Zn1 Na1 3.4661(19) 11_667 ?
Zn1 Na1 3.4661(19) 2_655 ?
Zn1 Na1 3.4661(19) 12_657 ?
Na1 O2 2.254(3) 11_667 ?
Na1 O2 2.254(3) 15_666 ?
Na1 O1 2.457(3) 5_657 ?
Na1 O1 2.458(3) . ?
Na1 O3 2.470(12) 5_657 ?
Na1 O3 2.470(12) . ?
Na1 Zn1 3.4661(19) 5_657 ?
O1 C1 1.290(4) . ?
O2 C1 1.239(4) . ?
O2 Na1 2.254(3) 12_657 ?
O3 C19 0.99(3) 5_657 ?
O3 C17 1.214(17) . ?
N1 C17 1.402(19) . ?
N1 C20 1.426(16) . ?
N1 C18 1.528(18) . ?
N1 C18 1.76(5) 5_657 ?
C1 C3 1.482(5) . ?
C2 C15 1.335(8) . ?
C2 C16 1.421(8) . ?
C3 C4 1.375(5) . ?
C3 C5 1.378(5) . ?
C4 C7 1.365(6) . ?
C5 C6 1.367(6) . ?
C6 C8 1.385(6) . ?
C7 C8 1.396(6) . ?
C8 C9 1.438(6) . ?
C9 C10 1.191(6) . ?
C10 C11 1.433(7) . ?
C11 C13 1.399(7) 7_647 ?
C11 C12 1.404(8) . ?
C12 C13 1.423(6) . ?
C12 C15 1.423(7) . ?
C13 C11 1.399(7) 7_647 ?
C13 C14 1.416(8) . ?
C14 C16 1.344(8) . ?
C18 C19 1.590(19) . ?
C20 C21 1.554(19) . ?

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 O1 105.66(16) 11_667 12_657 ?
O1 Zn1 O1 111.41(8) 11_667 2_655 ?
O1 Zn1 O1 111.41(8) 12_657 2_655 ?
O1 Zn1 O1 111.41(8) 11_667 . ?
O1 Zn1 O1 111.41(8) 12_657 . ?
O1 Zn1 O1 105.66(16) 2_655 . ?
O1 Zn1 Na1 91.36(9) 11_667 . ?
O1 Zn1 Na1 154.84(8) 12_657 . ?
O1 Zn1 Na1 77.97(8) 2_655 . ?
O1 Zn1 Na1 43.91(8) . . ?
O1 Zn1 Na1 43.90(8) 11_667 11_667 ?
O1 Zn1 Na1 77.97(8) 12_657 11_667 ?
O1 Zn1 Na1 91.36(9) 2_655 11_667 ?
O1 Zn1 Na1 154.84(7) . 11_667 ?
Na1 Zn1 Na1 126.23(5) . 11_667 ?
O1 Zn1 Na1 154.84(8) 11_667 2_655 ?
O1 Zn1 Na1 91.36(9) 12_657 2_655 ?
O1 Zn1 Na1 43.90(8) 2_655 2_655 ?
O1 Zn1 Na1 77.97(8) . 2_655 ?
Na1 Zn1 Na1 79.52(7) . 2_655 ?
Na1 Zn1 Na1 126.23(5) 11_667 2_655 ?
O1 Zn1 Na1 77.97(8) 11_667 12_657 ?
O1 Zn1 Na1 43.90(8) 12_657 12_657 ?
O1 Zn1 Na1 154.84(7) 2_655 12_657 ?
O1 Zn1 Na1 91.36(9) . 12_657 ?
Na1 Zn1 Na1 126.23(5) . 12_657 ?
Na1 Zn1 Na1 79.52(7) 11_667 12_657 ?
Na1 Zn1 Na1 126.23(5) 2_655 12_657 ?
O2 Na1 O2 166.2(2) 11_667 15_666 ?
O2 Na1 O1 108.85(10) 11_667 5_657 ?
O2 Na1 O1 79.38(9) 15_666 5_657 ?
O2 Na1 O1 79.38(9) 11_667 . ?
O2 Na1 O1 108.84(10) 15_666 . ?
O1 Na1 O1 109.30(17) 5_657 . ?
O2 Na1 O3 88.5(4) 11_667 5_657 ?
O2 Na1 O3 80.0(4) 15_666 5_657 ?
O1 Na1 O3 92.2(3) 5_657 5_657 ?
O1 Na1 O3 157.8(3) . 5_657 ?
O2 Na1 O3 80.0(4) 11_667 . ?
O2 Na1 O3 88.5(4) 15_666 . ?
O1 Na1 O3 157.8(3) 5_657 . ?
O1 Na1 O3 92.2(3) . . ?
O3 Na1 O3 67.2(5) 5_657 . ?
O2 Na1 Zn1 138.25(12) 11_667 5_657 ?
O2 Na1 Zn1 53.65(8) 15_666 5_657 ?
O1 Na1 Zn1 34.07(6) 5_657 5_657 ?
O1 Na1 Zn1 95.06(10) . 5_657 ?
O3 Na1 Zn1 106.3(3) 5_657 5_657 ?
O3 Na1 Zn1 141.8(4) . 5_657 ?
O2 Na1 Zn1 53.65(8) 11_667 . ?
O2 Na1 Zn1 138.25(12) 15_666 . ?
O1 Na1 Zn1 95.06(10) 5_657 . ?
O1 Na1 Zn1 34.08(6) . . ?
O3 Na1 Zn1 141.8(4) 5_657 . ?
O3 Na1 Zn1 106.3(3) . . ?
Zn1 Na1 Zn1 100.48(7) 5_657 . ?
C1 O1 Zn1 110.9(2) . . ?
C1 O1 Na1 124.1(2) . . ?
Zn1 O1 Na1 102.02(11) . . ?
C1 O2 Na1 155.1(3) . 12_657 ?
C19 O3 C17 31(3) 5_657 . ?
C19 O3 Na1 136(2) 5_657 . ?
C17 O3 Na1 166.8(16) . . ?
C17 N1 C20 139.8(18) . . ?
C17 N1 C18 121.9(16) . . ?
C20 N1 C18 96.3(14) . . ?
C17 N1 C18 73(2) . 5_657 ?
C20 N1 C18 124(3) . 5_657 ?
C18 N1 C18 61(3) . 5_657 ?
O2 C1 O1 123.1(4) . . ?
O2 C1 C3 119.9(4) . . ?
O1 C1 C3 116.9(4) . . ?
C15 C2 C16 119.2(7) . . ?
C4 C3 C5 119.5(4) . . ?
C4 C3 C1 121.5(4) . . ?
C5 C3 C1 118.9(4) . . ?
C7 C4 C3 121.0(4) . . ?
C6 C5 C3 119.8(4) . . ?
C5 C6 C8 121.4(5) . . ?
C4 C7 C8 120.1(4) . . ?
C6 C8 C7 118.2(4) . . ?
C6 C8 C9 120.7(5) . . ?
C7 C8 C9 121.1(5) . . ?
C10 C9 C8 176.7(6) . . ?
C9 C10 C11 178.4(6) . . ?
C13 C11 C12 121.6(5) 7_647 . ?
C13 C11 C10 118.8(6) 7_647 . ?
C12 C11 C10 119.5(6) . . ?
C11 C12 C13 117.8(6) . . ?
C11 C12 C15 122.7(5) . . ?
C13 C12 C15 119.5(6) . . ?
C11 C13 C14 122.3(5) 7_647 . ?
C11 C13 C12 120.6(6) 7_647 . ?
C14 C13 C12 117.0(6) . . ?
C16 C14 C13 121.7(6) . . ?
C2 C15 C12 121.4(6) . . ?
C14 C16 C2 121.1(7) . . ?
O3 C17 N1 113(2) . . ?
N1 C18 C19 113.0(18) . . ?
N1 C20 C21 129(2) . . ?

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.046




