# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_NENU-505
_database_code_depnum_ccdc_archive 'CCDC 1412229'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cl0 N5 O11 Zn2'
_chemical_formula_weight         639.17

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           'MONOCLINIC '
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  '-C 2yc '

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                   27.7680(11)
_cell_length_b                   7.9000(6)
_cell_length_c                   18.2980(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.3290(15)
_cell_angle_gamma                90.00
_cell_volume                     3810.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      28.28

_exptl_crystal_description       rhombus
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1300
_exptl_absorpt_coefficient_mu    1.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13597
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4701
_reflns_number_gt                3514
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97(Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (Brandenburg and Putz, 2008)'
_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 > 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)+(0.1231P)²+1.3884P] 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         4701
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_restrained_S_all      0.834
_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
Zn1 Zn 0.040976(10) 0.17319(4) 0.197153(15) 0.03203(13) Uani 1 1 d . . .
C2 C 0.08892(9) 0.0900(4) -0.02215(14) 0.0341(5) Uani 1 1 d . . .
H2 H 0.0565 0.0601 -0.0222 0.041 Uiso 1 1 calc R . .
O1 O 0.02387(7) -0.0561(3) -0.15170(12) 0.0514(5) Uani 1 1 d . . .
O2 O 0.08269(7) -0.0554(3) -0.21130(11) 0.0485(5) Uani 1 1 d . . .
C7 C 0.06728(9) -0.0233(3) -0.15505(14) 0.0339(5) Uani 1 1 d . . .
C3 C 0.10345(9) 0.0592(3) -0.08658(14) 0.0340(5) Uani 1 1 d . . .
N7 N 0.23368(9) 0.2226(5) -0.02749(18) 0.0628(8) Uani 1 1 d . . .
C4 C 0.15197(10) 0.1034(4) -0.08648(16) 0.0414(6) Uani 1 1 d . . .
H4 H 0.1623 0.0826 -0.1294 0.050 Uiso 1 1 calc R . .
O3 O 0.06231(9) 0.1476(3) 0.10822(13) 0.0563(6) Uani 1 1 d . . .
C1 C 0.12245(10) 0.1655(3) 0.04284(16) 0.0366(6) Uani 1 1 d . . .
C5 C 0.18484(10) 0.1792(4) -0.02116(19) 0.0444(7) Uani 1 1 d . . .
O5 O 0.02830(12) 0.4052(3) 0.21866(17) 0.0707(7) Uani 1 1 d . . .
C6 C 0.17062(10) 0.2111(4) 0.04299(17) 0.0435(7) Uani 1 1 d . . .
H6 H 0.1931 0.2627 0.0860 0.052 Uiso 1 1 calc R . .
O4 O 0.13526(12) 0.2655(5) 0.16989(16) 0.0901(10) Uani 1 1 d . . .
C8 C 0.10667(12) 0.1970(4) 0.11288(18) 0.0462(7) Uani 1 1 d . . .
N1 N 0.0986(8) 0.6576(15) 0.0437(14) 0.324(11) Uani 1 1 d . . .
H1A H 0.0758 0.7424 0.0320 0.389 Uiso 1 1 calc R . .
H1B H 0.0842 0.5639 0.0556 0.389 Uiso 1 1 calc R . .
C10 C 0.1218(11) 0.625(2) -0.0213(18) 0.40(2) Uani 1 1 d . . .
H10A H 0.0956 0.5893 -0.0669 0.596 Uiso 1 1 calc R . .
H10B H 0.1471 0.5380 -0.0056 0.596 Uiso 1 1 calc R . .
H10C H 0.1371 0.7272 -0.0319 0.596 Uiso 1 1 calc R . .
N2 N 0.0000 0.4749(6) 0.2500 0.0814(14) Uani 1 2 d S . .
O6 O 0.0000 0.6663(8) 0.2500 0.243(8) Uani 1 2 d S . .
C11 C 0.1421(15) 0.702(2) 0.101(3) 0.75(6) Uani 1 1 d . . .
H11A H 0.1337 0.7340 0.1464 1.131 Uiso 1 1 calc R . .
H11B H 0.1580 0.7956 0.0844 1.131 Uiso 1 1 calc R . .
H11C H 0.1650 0.6074 0.1130 1.131 Uiso 1 1 calc R . .


_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
Zn1 O3 1.910(2) . ?
Zn1 O5 1.930(2) . ?
Zn1 O2 1.9476(19) 6_556 ?
Zn1 O1 1.9615(18) 5 ?
C2 C3 1.382(3) . ?
C2 C1 1.393(4) . ?
C2 H2 0.9300 . ?
O1 C7 1.253(3) . ?
O1 Zn1 1.9615(18) 5 ?
O2 C7 1.259(3) . ?
O2 Zn1 1.9476(19) 6 ?
C7 C3 1.487(3) . ?
C3 C4 1.391(3) . ?
N7 N7 1.203(5) 7 ?
N7 C5 1.438(3) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
O3 C8 1.269(4) . ?
C1 C6 1.384(4) . ?
C1 C8 1.500(4) . ?
C5 C6 1.374(4) . ?
O5 N2 1.238(3) . ?
C6 H6 0.9300 . ?
O4 C8 1.221(4) . ?
N1 C11 1.38(3) . ?
N1 C10 1.54(2) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N2 O5 1.238(3) 2 ?
N2 O6 1.512(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
O3 Zn1 O5 113.55(11) . . ?
O3 Zn1 O2 114.98(10) . 6_556 ?
O5 Zn1 O2 112.06(12) . 6_556 ?
O3 Zn1 O1 94.48(9) . 5 ?
O5 Zn1 O1 109.41(12) . 5 ?
O2 Zn1 O1 110.97(10) 6_556 5 ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C7 O1 Zn1 147.75(19) . 5 ?
C7 O2 Zn1 122.44(17) . 6 ?
O1 C7 O2 125.3(2) . . ?
O1 C7 C3 117.0(2) . . ?
O2 C7 C3 117.6(2) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 C7 119.7(2) . . ?
C4 C3 C7 120.6(2) . . ?
N7 N7 C5 120.0(4) 7 . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C8 O3 Zn1 117.7(2) . . ?
C6 C1 C2 119.9(3) . . ?
C6 C1 C8 119.8(3) . . ?
C2 C1 C8 120.3(2) . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 N7 123.8(3) . . ?
C4 C5 N7 114.5(3) . . ?
N2 O5 Zn1 134.4(3) . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O4 C8 O3 123.4(3) . . ?
O4 C8 C1 121.2(3) . . ?
O3 C8 C1 115.4(3) . . ?
C11 N1 C10 99(4) . . ?
C11 N1 H1A 112.0 . . ?
C10 N1 H1A 112.0 . . ?
C11 N1 H1B 112.0 . . ?
C10 N1 H1B 112.0 . . ?
H1A N1 H1B 109.7 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 N2 O5 127.2(5) 2 . ?
O5 N2 O6 116.4(2) 2 . ?
O5 N2 O6 116.4(2) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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 O1 C7 O2 10.9(6) 5 . . . ?
Zn1 O1 C7 C3 -168.6(3) 5 . . . ?
Zn1 O2 C7 O1 -2.7(4) 6 . . . ?
Zn1 O2 C7 C3 176.84(18) 6 . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C7 179.3(3) . . . . ?
O1 C7 C3 C2 2.4(4) . . . . ?
O2 C7 C3 C2 -177.1(3) . . . . ?
O1 C7 C3 C4 -178.5(3) . . . . ?
O2 C7 C3 C4 2.0(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C7 C3 C4 C5 -179.6(3) . . . . ?
O5 Zn1 O3 C8 71.6(3) . . . . ?
O2 Zn1 O3 C8 -59.3(3) 6_556 . . . ?
O1 Zn1 O3 C8 -175.0(3) 5 . . . ?
C3 C2 C1 C6 0.4(4) . . . . ?
C3 C2 C1 C8 -179.4(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C3 C4 C5 N7 -178.9(3) . . . . ?
N7 N7 C5 C6 6.4(7) 7 . . . ?
N7 N7 C5 C4 -174.6(5) 7 . . . ?
O3 Zn1 O5 N2 151.3(3) . . . . ?
O2 Zn1 O5 N2 -76.4(3) 6_556 . . . ?
O1 Zn1 O5 N2 47.2(3) 5 . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
N7 C5 C6 C1 179.4(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C8 C1 C6 C5 179.0(3) . . . . ?
Zn1 O3 C8 O4 -3.0(5) . . . . ?
Zn1 O3 C8 C1 176.9(2) . . . . ?
C6 C1 C8 O4 1.4(5) . . . . ?
C2 C1 C8 O4 -178.8(4) . . . . ?
C6 C1 C8 O3 -178.4(3) . . . . ?
C2 C1 C8 O3 1.3(4) . . . . ?
Zn1 O5 N2 O5 3.8(2) . . . 2 ?
Zn1 O5 N2 O6 -176.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.395
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.105
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
_platon_squeeze_void_content
1 0.250 -0.051 0.290 587 144 ' '
2 0.500 0.000 0.000 58 6 ' '
3 0.500 0.000 0.500 58 6 ' '
4 0.750 -0.112 0.410 587 144 ' '
5 0.000 0.500 0.500 58 6 ' '
6 1.000 0.500 1.000 58 6 ' '
_platon_squeeze_details          
;
;
