# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1409437'
_audit_update_record             
;
2015-08-29 deposited with the CCDC.
2015-10-08 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            'C36 H38 N10 O10 Zn2'
_chemical_formula_weight         901.42

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.471(4)
_cell_length_b                   8.7703(17)
_cell_length_c                   19.775(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3897.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       acicular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.301
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            13805
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.812
_diffrn_reflns_theta_max         25.067
_diffrn_reflns_theta_full        25.067
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3457
_reflns_number_gt                2686
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1543P)²+9.8107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3457
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2441
_refine_ls_wR_factor_gt          0.2216
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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_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 0.21398(3) -0.57919(8) -0.04170(3) 0.0430(3) Uani 1 1 d . . . . .
O1 O 0.2500 -0.7500 -0.0847(3) 0.0544(15) Uani 1 2 d S T P . .
O2 O 0.0845(2) -0.6794(8) -0.0311(2) 0.0766(17) Uani 1 1 d . . . . .
O3 O 0.1629(2) -0.6416(6) 0.0333(2) 0.0562(12) Uani 1 1 d . . . . .
N1 N 0.1930(3) -0.4294(7) -0.1106(3) 0.0703(18) Uani 1 1 d . . . . .
N2 N 0.1468(2) -0.3868(6) -0.1265(3) 0.0498(13) Uani 1 1 d . . . . .
N3 N 0.1027(3) -0.3290(9) -0.1431(4) 0.086(2) Uani 1 1 d . . . . .
N4 N -0.03210(19) -0.9741(5) 0.2837(2) 0.0364(10) Uani 1 1 d . . . . .
N5 N -0.2212(2) -0.5289(6) 0.4862(3) 0.0439(12) Uani 1 1 d . . . . .
C1 C 0.1110(2) -0.6937(7) 0.0226(3) 0.0412(13) Uani 1 1 d . . . . .
C2 C 0.0833(2) -0.7791(6) 0.0796(3) 0.0370(12) Uani 1 1 d . . . . .
C3 C 0.1092(2) -0.7872(7) 0.1431(3) 0.0418(13) Uani 1 1 d . . . . .
H3 H 0.1438 -0.7326 0.1518 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0312(3) -0.8616(8) 0.0692(3) 0.0477(14) Uani 1 1 d . . . . .
H4 H 0.0127 -0.8577 0.0271 0.057 Uiso 1 1 calc R U . . .
C5 C 0.0841(3) -0.8756(7) 0.1936(3) 0.0438(14) Uani 1 1 d . . . . .
H5 H 0.1021 -0.8795 0.2359 0.053 Uiso 1 1 calc R U . . .
C6 C 0.0064(3) -0.9491(8) 0.1197(3) 0.0509(15) Uani 1 1 d . . . . .
H6 H -0.0286 -1.0026 0.1114 0.061 Uiso 1 1 calc R U . . .
C7 C 0.0328(2) -0.9581(6) 0.1822(3) 0.0391(12) Uani 1 1 d . . . . .
C8 C 0.0073(3) -1.0587(6) 0.2365(3) 0.0453(14) Uani 1 1 d . . . . .
H8A H -0.0152 -1.1404 0.2156 0.054 Uiso 1 1 calc R U . . .
H8B H 0.0396 -1.1044 0.2619 0.054 Uiso 1 1 calc R U . . .
C9 C -0.0129(3) -0.9346(7) 0.3455(3) 0.0424(13) Uani 1 1 d . . . . .
H9 H 0.0245 -0.9657 0.3598 0.051 Uiso 1 1 calc R U . . .
C10 C -0.0871(3) -0.9337(7) 0.2631(3) 0.0447(14) Uani 1 1 d . . . . .
H10 H -0.1002 -0.9632 0.2205 0.054 Uiso 1 1 calc R U . . .
C11 C -0.0481(2) -0.8486(7) 0.3879(3) 0.0400(13) Uani 1 1 d . . . . .
H11 H -0.0340 -0.8204 0.4303 0.048 Uiso 1 1 calc R U . . .
C12 C -0.1234(2) -0.8514(7) 0.3032(3) 0.0438(14) Uani 1 1 d . . . . .
H12 H -0.1613 -0.8261 0.2879 0.053 Uiso 1 1 calc R U . . .
C13 C -0.1050(2) -0.8036(6) 0.3672(3) 0.0358(12) Uani 1 1 d . . . . .
C14 C -0.1440(2) -0.7061(6) 0.4090(3) 0.0337(11) Uani 1 1 d . . . . .
C15 C -0.1393(3) -0.7014(8) 0.4788(3) 0.0493(15) Uani 1 1 d . . . . .
H15 H -0.1104 -0.7582 0.5010 0.059 Uiso 1 1 calc R U . . .
C16 C -0.1877(3) -0.6173(7) 0.3796(3) 0.0456(14) Uani 1 1 d . . . . .
H16 H -0.1915 -0.6150 0.3328 0.055 Uiso 1 1 calc R U . . .
C17 C -0.1783(3) -0.6111(8) 0.5150(3) 0.0541(17) Uani 1 1 d . . . . .
H17 H -0.1745 -0.6076 0.5618 0.065 Uiso 1 1 calc R U . . .
C18 C -0.2253(3) -0.5330(8) 0.4189(3) 0.0463(14) Uani 1 1 d . . . . .
H18 H -0.2550 -0.4761 0.3979 0.056 Uiso 1 1 calc R U . . .
O6 O -0.2386(6) -0.1732(13) 0.2451(7) 0.198(5) Uiso 1 1 d . . . . .
O4 O -0.1133(3) -0.1949(9) 0.1536(3) 0.108(2) Uani 1 1 d . . . . .
O5 O -0.2500 -0.7500 0.2269(8) 0.168(6) Uiso 1 2 d S . 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 1.903(3) . ?
Zn1 N1 1.951(6) . ?
Zn1 O3 1.954(4) . ?
Zn1 N5 2.056(5) 3_545 ?
O1 Zn1 1.903(3) 2_535 ?
O2 C1 1.223(7) . ?
O3 C1 1.270(7) . ?
N1 N2 1.147(8) . ?
N2 N3 1.160(9) . ?
N4 C9 1.340(7) . ?
N4 C10 1.348(7) . ?
N4 C8 1.486(7) . ?
N5 C17 1.330(8) . ?
N5 C18 1.335(8) . ?
N5 Zn1 2.056(5) 3_445 ?
C1 C2 1.490(8) . ?
C2 C3 1.385(8) . ?
C2 C4 1.392(8) . ?
C3 C5 1.385(8) . ?
C3 H3 0.9300 . ?
C4 C6 1.377(9) . ?
C4 H4 0.9300 . ?
C5 C7 1.380(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.503(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.378(8) . ?
C9 H9 0.9300 . ?
C10 C12 1.347(8) . ?
C10 H10 0.9300 . ?
C11 C13 1.399(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.476(7) . ?
C14 C16 1.381(8) . ?
C14 C15 1.385(8) . ?
C15 C17 1.381(8) . ?
C15 H15 0.9300 . ?
C16 C18 1.365(9) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O6 O6 1.44(2) 2_445 ?

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 108.7(3) . . ?
O1 Zn1 O3 111.6(2) . . ?
N1 Zn1 O3 125.2(3) . . ?
O1 Zn1 N5 107.45(17) . 3_545 ?
N1 Zn1 N5 103.5(2) . 3_545 ?
O3 Zn1 N5 98.07(19) . 3_545 ?
Zn1 O1 Zn1 127.0(3) 2_535 . ?
C1 O3 Zn1 120.9(4) . . ?
N2 N1 Zn1 129.0(5) . . ?
N1 N2 N3 173.0(7) . . ?
C9 N4 C10 120.1(5) . . ?
C9 N4 C8 120.7(5) . . ?
C10 N4 C8 119.2(5) . . ?
C17 N5 C18 117.5(5) . . ?
C17 N5 Zn1 122.3(4) . 3_445 ?
C18 N5 Zn1 119.7(4) . 3_445 ?
O2 C1 O3 123.7(6) . . ?
O2 C1 C2 120.3(5) . . ?
O3 C1 C2 116.0(5) . . ?
C3 C2 C4 117.4(5) . . ?
C3 C2 C1 122.4(5) . . ?
C4 C2 C1 120.1(5) . . ?
C5 C3 C2 120.8(5) . . ?
C5 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C6 C4 C2 121.5(5) . . ?
C6 C4 H4 119.3 . . ?
C2 C4 H4 119.3 . . ?
C7 C5 C3 121.1(5) . . ?
C7 C5 H5 119.5 . . ?
C3 C5 H5 119.5 . . ?
C7 C6 C4 120.7(6) . . ?
C7 C6 H6 119.6 . . ?
C4 C6 H6 119.6 . . ?
C6 C7 C5 118.5(5) . . ?
C6 C7 C8 120.8(5) . . ?
C5 C7 C8 120.6(5) . . ?
N4 C8 C7 112.5(4) . . ?
N4 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N4 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N4 C9 C11 120.8(5) . . ?
N4 C9 H9 119.6 . . ?
C11 C9 H9 119.6 . . ?
C12 C10 N4 121.2(5) . . ?
C12 C10 H10 119.4 . . ?
N4 C10 H10 119.4 . . ?
C9 C11 C13 120.0(5) . . ?
C9 C11 H11 120.0 . . ?
C13 C11 H11 120.0 . . ?
C10 C12 C13 120.9(5) . . ?
C10 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C11 116.8(5) . . ?
C12 C13 C14 120.4(5) . . ?
C11 C13 C14 122.8(5) . . ?
C16 C14 C15 117.1(5) . . ?
C16 C14 C13 120.9(5) . . ?
C15 C14 C13 122.0(5) . . ?
C17 C15 C14 119.1(5) . . ?
C17 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C18 C16 C14 120.4(6) . . ?
C18 C16 H16 119.8 . . ?
C14 C16 H16 119.8 . . ?
N5 C17 C15 123.3(6) . . ?
N5 C17 H17 118.4 . . ?
C15 C17 H17 118.4 . . ?
N5 C18 C16 122.6(6) . . ?
N5 C18 H18 118.7 . . ?
C16 C18 H18 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O3 C1 O2 -16.1(10) . . . . ?
Zn1 O3 C1 C2 162.6(4) . . . . ?
O2 C1 C2 C3 -174.3(6) . . . . ?
O3 C1 C2 C3 7.0(8) . . . . ?
O2 C1 C2 C4 9.3(9) . . . . ?
O3 C1 C2 C4 -169.3(6) . . . . ?
C4 C2 C3 C5 0.6(8) . . . . ?
C1 C2 C3 C5 -175.8(5) . . . . ?
C3 C2 C4 C6 -0.5(9) . . . . ?
C1 C2 C4 C6 176.1(6) . . . . ?
C2 C3 C5 C7 0.1(9) . . . . ?
C2 C4 C6 C7 -0.4(10) . . . . ?
C4 C6 C7 C5 1.1(9) . . . . ?
C4 C6 C7 C8 -177.4(6) . . . . ?
C3 C5 C7 C6 -0.9(9) . . . . ?
C3 C5 C7 C8 177.5(5) . . . . ?
C9 N4 C8 C7 -103.2(6) . . . . ?
C10 N4 C8 C7 75.1(7) . . . . ?
C6 C7 C8 N4 -96.0(7) . . . . ?
C5 C7 C8 N4 85.6(7) . . . . ?
C10 N4 C9 C11 -2.0(8) . . . . ?
C8 N4 C9 C11 176.2(5) . . . . ?
C9 N4 C10 C12 1.1(9) . . . . ?
C8 N4 C10 C12 -177.2(6) . . . . ?
N4 C9 C11 C13 1.1(9) . . . . ?
N4 C10 C12 C13 0.8(9) . . . . ?
C10 C12 C13 C11 -1.6(9) . . . . ?
C10 C12 C13 C14 176.5(6) . . . . ?
C9 C11 C13 C12 0.6(8) . . . . ?
C9 C11 C13 C14 -177.4(5) . . . . ?
C12 C13 C14 C16 -23.0(8) . . . . ?
C11 C13 C14 C16 155.0(6) . . . . ?
C12 C13 C14 C15 155.8(6) . . . . ?
C11 C13 C14 C15 -26.3(8) . . . . ?
C16 C14 C15 C17 0.7(9) . . . . ?
C13 C14 C15 C17 -178.1(6) . . . . ?
C15 C14 C16 C18 -1.9(9) . . . . ?
C13 C14 C16 C18 177.0(6) . . . . ?
C18 N5 C17 C15 -1.3(10) . . . . ?
Zn1 N5 C17 C15 170.8(6) 3_445 . . . ?
C14 C15 C17 N5 0.9(11) . . . . ?
C17 N5 C18 C16 0.1(10) . . . . ?
Zn1 N5 C18 C16 -172.3(5) 3_445 . . . ?
C14 C16 C18 N5 1.5(10) . . . . ?

_refine_diff_density_max         1.502
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.135

