# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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 1559450'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O6 Zn'
_chemical_formula_weight         356.62

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2143(5)
_cell_length_b                   9.7414(6)
_cell_length_c                   10.4899(6)
_cell_angle_alpha                107.352(2)
_cell_angle_beta                 101.099(2)
_cell_angle_gamma                111.798(2)
_cell_volume                     699.00(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16950
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0100
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.20
_reflns_number_total             2499
_reflns_number_gt                2423
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0378P)²+1.0070P] 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         2499
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.70183(3) 0.64748(3) 0.49634(2) 0.02307(10) Uani 1 1 d . . .
N1 N -0.1154(2) -0.2383(2) -0.29944(19) 0.0221(4) Uani 1 1 d . . .
O1 O 0.6974(6) 0.5105(7) 0.1078(3) 0.176(3) Uani 1 1 d . . .
H1A H 0.6780 0.4174 0.1046 0.211 Uiso 1 1 d R . .
H1B H 0.6007 0.5168 0.1200 0.211 Uiso 1 1 d R . .
O2 O 0.6192(2) -0.21335(19) 0.43009(16) 0.0271(3) Uani 1 1 d . . .
O3 O 0.4596(3) -0.3904(2) 0.20562(19) 0.0377(4) Uani 1 1 d . . .
O4 O 0.8034(2) 0.3802(2) 0.50376(19) 0.0387(4) Uani 1 1 d . . .
O5 O 0.5577(2) 0.40862(17) 0.41189(17) 0.0251(3) Uani 1 1 d . . .
O6 O 0.9010(3) 0.6632(2) 0.3969(2) 0.0369(4) Uani 1 1 d . . .
H6C H 0.8398 0.6143 0.2957 0.055 Uiso 1 1 d R . .
H6D H 0.9675 0.6074 0.4231 0.055 Uiso 1 1 d R . .
C1 C 0.5211(3) -0.2549(3) 0.3033(2) 0.0212(4) Uani 1 1 d . . .
C2 C 0.4801(3) -0.1285(3) 0.2704(2) 0.0201(4) Uani 1 1 d . . .
C3 C 0.5790(3) 0.0347(3) 0.3604(2) 0.0198(4) Uani 1 1 d . . .
H3 H 0.6713 0.0686 0.4460 0.024 Uiso 1 1 calc R . .
C4 C 0.6452(3) 0.3236(2) 0.4209(2) 0.0216(4) Uani 1 1 d . . .
C5 C 0.5401(3) 0.1474(2) 0.3226(2) 0.0192(4) Uani 1 1 d . . .
C6 C 0.3420(3) -0.1774(3) 0.1430(2) 0.0240(5) Uani 1 1 d . . .
H6A H 0.2748 -0.2868 0.0832 0.029 Uiso 1 1 calc R . .
C7 C 0.4030(3) 0.0972(3) 0.1944(2) 0.0213(4) Uani 1 1 d . . .
H7 H 0.3782 0.1732 0.1695 0.026 Uiso 1 1 calc R . .
C8 C 0.3021(3) -0.0665(3) 0.1028(2) 0.0220(4) Uani 1 1 d . . .
C9 C 0.1547(3) -0.1235(3) -0.0342(2) 0.0226(4) Uani 1 1 d . . .
C10 C 0.0068(4) -0.2799(3) -0.0967(3) 0.0323(5) Uani 1 1 d . . .
H10 H -0.0046 -0.3485 -0.0499 0.039 Uiso 1 1 calc R . .
C11 C 0.1554(3) -0.0259(3) -0.1068(2) 0.0233(4) Uani 1 1 d . . .
H11 H 0.2490 0.0804 -0.0675 0.028 Uiso 1 1 calc R . .
C12 C 0.0160(4) 0.0244(3) -0.3122(3) 0.0340(6) Uani 1 1 d . . .
H12A H 0.0601 -0.0011 -0.3902 0.051 Uiso 1 1 calc R . .
H12B H 0.0952 0.1352 -0.2472 0.051 Uiso 1 1 calc R . .
H12C H -0.1093 0.0085 -0.3476 0.051 Uiso 1 1 calc R . .
C13 C 0.0191(3) -0.0834(3) -0.2372(2) 0.0217(4) Uani 1 1 d . . .
C14 C -0.1214(3) -0.3319(3) -0.2272(3) 0.0302(5) Uani 1 1 d . . .
H14 H -0.2173 -0.4372 -0.2677 0.036 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 1.9608(15) 1_565 ?
Zn1 O5 1.9803(15) . ?
Zn1 N1 2.0447(18) 1_666 ?
Zn1 O6 2.0866(18) . ?
Zn1 O5 2.4510(16) 2_666 ?
N1 C14 1.342(3) . ?
N1 C13 1.350(3) . ?
N1 Zn1 2.0447(17) 1_444 ?
O1 H1A 0.8499 . ?
O1 H1B 0.8500 . ?
O2 C1 1.267(3) . ?
O2 Zn1 1.9608(15) 1_545 ?
O3 C1 1.244(3) . ?
O4 C4 1.223(3) . ?
O5 C4 1.294(3) . ?
O5 Zn1 2.4510(16) 2_666 ?
O6 H6C 0.9601 . ?
O6 H6D 0.9600 . ?
C1 C2 1.505(3) . ?
C2 C3 1.389(3) . ?
C2 C6 1.391(3) . ?
C3 C5 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.502(3) . ?
C5 C7 1.390(3) . ?
C6 C8 1.390(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.397(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.481(3) . ?
C9 C11 1.384(3) . ?
C9 C10 1.396(3) . ?
C10 C14 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C13 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.493(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14 0.9300 . ?

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 O5 123.16(7) 1_565 . ?
O2 Zn1 N1 113.99(7) 1_565 1_666 ?
O5 Zn1 N1 118.83(7) . 1_666 ?
O2 Zn1 O6 95.98(7) 1_565 . ?
O5 Zn1 O6 97.38(7) . . ?
N1 Zn1 O6 96.65(7) 1_666 . ?
O2 Zn1 O5 86.31(6) 1_565 2_666 ?
O5 Zn1 O5 75.19(6) . 2_666 ?
N1 Zn1 O5 89.20(6) 1_666 2_666 ?
O6 Zn1 O5 172.18(6) . 2_666 ?
C14 N1 C13 118.07(18) . . ?
C14 N1 Zn1 115.86(14) . 1_444 ?
C13 N1 Zn1 125.78(14) . 1_444 ?
H1A O1 H1B 103.1 . . ?
C1 O2 Zn1 124.25(14) . 1_545 ?
C4 O5 Zn1 118.95(13) . . ?
C4 O5 Zn1 114.98(13) . 2_666 ?
Zn1 O5 Zn1 104.81(6) . 2_666 ?
Zn1 O6 H6C 109.4 . . ?
Zn1 O6 H6D 109.4 . . ?
H6C O6 H6D 109.5 . . ?
O3 C1 O2 124.71(19) . . ?
O3 C1 C2 118.57(19) . . ?
O2 C1 C2 116.72(18) . . ?
C3 C2 C6 119.27(19) . . ?
C3 C2 C1 122.28(18) . . ?
C6 C2 C1 118.41(19) . . ?
C2 C3 C5 120.04(19) . . ?
C2 C3 H3 120.0 . . ?
C5 C3 H3 120.0 . . ?
O4 C4 O5 123.21(19) . . ?
O4 C4 C5 120.88(19) . . ?
O5 C4 C5 115.91(18) . . ?
C7 C5 C3 120.16(19) . . ?
C7 C5 C4 119.78(18) . . ?
C3 C5 C4 120.06(18) . . ?
C8 C6 C2 121.5(2) . . ?
C8 C6 H6A 119.2 . . ?
C2 C6 H6A 119.2 . . ?
C5 C7 C8 120.49(19) . . ?
C5 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C6 C8 C7 118.50(19) . . ?
C6 C8 C9 119.83(19) . . ?
C7 C8 C9 121.67(19) . . ?
C11 C9 C10 116.47(19) . . ?
C11 C9 C8 122.25(19) . . ?
C10 C9 C8 121.28(19) . . ?
C14 C10 C9 119.8(2) . . ?
C14 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C9 C11 C13 121.3(2) . . ?
C9 C11 H11 119.4 . . ?
C13 C11 H11 119.4 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C11 120.92(19) . . ?
N1 C13 C12 118.03(19) . . ?
C11 C13 C12 121.0(2) . . ?
N1 C14 C10 123.2(2) . . ?
N1 C14 H14 118.4 . . ?
C10 C14 H14 118.4 . . ?

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
O2 Zn1 O5 C4 154.41(15) 1_565 . . . ?
N1 Zn1 O5 C4 -49.52(18) 1_666 . . . ?
O6 Zn1 O5 C4 52.28(17) . . . . ?
O5 Zn1 O5 C4 -130.20(19) 2_666 . . . ?
O2 Zn1 O5 Zn1 -75.39(9) 1_565 . . 2_666 ?
N1 Zn1 O5 Zn1 80.68(8) 1_666 . . 2_666 ?
O6 Zn1 O5 Zn1 -177.51(6) . . . 2_666 ?
O5 Zn1 O5 Zn1 0.0 2_666 . . 2_666 ?
Zn1 O2 C1 O3 2.3(3) 1_545 . . . ?
Zn1 O2 C1 C2 -176.70(13) 1_545 . . . ?
O3 C1 C2 C3 -163.5(2) . . . . ?
O2 C1 C2 C3 15.6(3) . . . . ?
O3 C1 C2 C6 14.5(3) . . . . ?
O2 C1 C2 C6 -166.4(2) . . . . ?
C6 C2 C3 C5 -0.3(3) . . . . ?
C1 C2 C3 C5 177.68(19) . . . . ?
Zn1 O5 C4 O4 16.4(3) . . . . ?
Zn1 O5 C4 O4 -109.1(2) 2_666 . . . ?
Zn1 O5 C4 C5 -163.85(14) . . . . ?
Zn1 O5 C4 C5 70.7(2) 2_666 . . . ?
C2 C3 C5 C7 -0.3(3) . . . . ?
C2 C3 C5 C4 179.13(19) . . . . ?
O4 C4 C5 C7 -153.1(2) . . . . ?
O5 C4 C5 C7 27.1(3) . . . . ?
O4 C4 C5 C3 27.4(3) . . . . ?
O5 C4 C5 C3 -152.4(2) . . . . ?
C3 C2 C6 C8 0.8(3) . . . . ?
C1 C2 C6 C8 -177.2(2) . . . . ?
C3 C5 C7 C8 0.4(3) . . . . ?
C4 C5 C7 C8 -179.0(2) . . . . ?
C2 C6 C8 C7 -0.7(3) . . . . ?
C2 C6 C8 C9 179.6(2) . . . . ?
C5 C7 C8 C6 0.1(3) . . . . ?
C5 C7 C8 C9 179.8(2) . . . . ?
C6 C8 C9 C11 -153.8(2) . . . . ?
C7 C8 C9 C11 26.5(3) . . . . ?
C6 C8 C9 C10 26.3(3) . . . . ?
C7 C8 C9 C10 -153.4(2) . . . . ?
C11 C9 C10 C14 3.8(4) . . . . ?
C8 C9 C10 C14 -176.3(2) . . . . ?
C10 C9 C11 C13 -2.1(3) . . . . ?
C8 C9 C11 C13 177.9(2) . . . . ?
C14 N1 C13 C11 4.6(3) . . . . ?
Zn1 N1 C13 C11 -169.01(16) 1_444 . . . ?
C14 N1 C13 C12 -174.9(2) . . . . ?
Zn1 N1 C13 C12 11.5(3) 1_444 . . . ?
C9 C11 C13 N1 -2.1(3) . . . . ?
C9 C11 C13 C12 177.4(2) . . . . ?
C13 N1 C14 C10 -3.0(4) . . . . ?
Zn1 N1 C14 C10 171.3(2) 1_444 . . . ?
C9 C10 C14 N1 -1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.059
