# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ZJU-108
_database_code_depnum_ccdc_archive 'CCDC 1555718'
_audit_update_record             
;
2017-08-06 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H0 N O5 Zn'
_chemical_formula_weight         315.51

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.4995(2)
_cell_length_b                   18.1405(5)
_cell_length_c                   10.6050(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.155(2)
_cell_angle_gamma                90
_cell_volume                     1230.79(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.251
_cell_measurement_theta_max      25.9975

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.012
_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_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            25915
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         26.091
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2422
_reflns_number_gt                2146
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2422
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_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 1.14072(5) 0.05526(2) 0.19239(3) 0.02278(19) Uani 1 1 d . . . . .
O2 O 0.9626(3) 0.14096(12) 0.1467(2) 0.0331(5) Uani 1 1 d . . . . .
O4 O 1.2617(4) 0.03914(13) 0.0348(2) 0.0336(5) Uani 1 1 d . . . . .
O5 O 0.5362(4) 0.48353(12) 0.2387(2) 0.0428(6) Uani 1 1 d . . . . .
O14 O 0.6543(3) 0.09739(11) 0.0495(2) 0.0341(6) Uani 1 1 d . . . . .
O17 O 0.2376(5) 0.42657(14) 0.2389(3) 0.0505(7) Uani 1 1 d . . . . .
N3 N -0.1217(4) 0.39887(15) -0.1808(2) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.0552(6) 0.43814(16) -0.1453(4) 0.0306(8) Uani 1 1 d . . . . .
C2 C 0.2240(5) 0.41169(17) -0.0615(3) 0.0315(7) Uani 1 1 d . . . . .
C3 C -0.1289(5) 0.33044(16) -0.1319(3) 0.0317(7) Uani 1 1 d . . . . .
C7 C 0.7672(5) 0.14683(16) 0.1055(3) 0.0251(6) Uani 1 1 d . . . . .
C9A C 0.4830(4) 0.24265(15) 0.0605(3) 0.0238(6) Uani 1 1 d . . . . .
C10 C 0.0349(5) 0.30046(16) -0.0454(3) 0.0302(7) Uani 1 1 d . . . . .
C11 C 0.6773(5) 0.22082(15) 0.1269(3) 0.0242(6) Uani 1 1 d . . . . .
C12 C 0.4026(4) 0.31228(15) 0.0799(3) 0.0237(6) Uani 1 1 d . . . . .
C13 C 0.2147(5) 0.34114(16) -0.0075(3) 0.0244(6) Uani 1 1 d . . . . .
C14 C 0.5139(5) 0.35786(16) 0.1755(3) 0.0287(7) Uani 1 1 d . . . . .
C15 C 0.7103(6) 0.33733(17) 0.2383(3) 0.0328(7) Uani 1 1 d . . . . .
C16 C 0.4185(6) 0.42666(17) 0.2188(3) 0.0327(8) Uani 1 1 d . . . . .
C18 C 0.7927(5) 0.26976(17) 0.2145(3) 0.0325(7) Uani 1 1 d . . . . .


_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 1.948(2) . ?
Zn1 O5 1.961(2) 2_645 ?
Zn1 O4 1.990(2) . ?
Zn1 N3 2.038(2) 4_766 ?
Zn1 C16 2.570(3) 2_645 ?
O2 C7 1.273(4) . ?
O5 C16 1.279(4) . ?
O5 Zn1 1.961(2) 2_655 ?
O14 C7 1.242(4) . ?
O17 C16 1.231(5) . ?
N3 C1 1.349(4) . ?
N3 C3 1.349(4) . ?
N3 Zn1 2.038(2) 4_465 ?
C1 C2 1.371(5) . ?
C2 C13 1.408(4) . ?
C3 C10 1.388(4) . ?
C7 C11 1.497(4) . ?
C9A C11 1.390(4) . ?
C9A C12 1.396(4) . ?
C10 C13 1.380(4) . ?
C11 C18 1.403(4) . ?
C12 C14 1.405(4) . ?
C12 C13 1.492(4) . ?
C14 C15 1.383(5) . ?
C14 C16 1.501(4) . ?
C15 C18 1.379(5) . ?
C16 Zn1 2.570(3) 2_655 ?

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 105.11(10) . 2_645 ?
O2 Zn1 O4 102.34(10) . . ?
O5 Zn1 O4 124.06(11) 2_645 . ?
O2 Zn1 N3 100.72(10) . 4_766 ?
O5 Zn1 N3 116.78(10) 2_645 4_766 ?
O4 Zn1 N3 104.40(10) . 4_766 ?
O2 Zn1 C16 134.02(11) . 2_645 ?
O5 Zn1 C16 29.02(12) 2_645 2_645 ?
O4 Zn1 C16 106.35(11) . 2_645 ?
N3 Zn1 C16 105.88(11) 4_766 2_645 ?
C7 O2 Zn1 131.7(2) . . ?
C16 O5 Zn1 102.9(2) . 2_655 ?
C1 N3 C3 117.7(3) . . ?
C1 N3 Zn1 118.5(2) . 4_465 ?
C3 N3 Zn1 123.8(2) . 4_465 ?
N3 C1 C2 122.8(3) . . ?
C1 C2 C13 119.6(3) . . ?
N3 C3 C10 122.7(3) . . ?
O14 C7 O2 125.0(3) . . ?
O14 C7 C11 120.4(3) . . ?
O2 C7 C11 114.6(3) . . ?
C11 C9A C12 120.9(3) . . ?
C13 C10 C3 119.6(3) . . ?
C9A C11 C18 119.1(3) . . ?
C9A C11 C7 121.5(3) . . ?
C18 C11 C7 119.4(3) . . ?
C9A C12 C14 118.7(3) . . ?
C9A C12 C13 120.9(3) . . ?
C14 C12 C13 120.2(2) . . ?
C10 C13 C2 117.6(3) . . ?
C10 C13 C12 123.5(3) . . ?
C2 C13 C12 118.8(3) . . ?
C15 C14 C12 120.2(3) . . ?
C15 C14 C16 118.2(3) . . ?
C12 C14 C16 121.5(3) . . ?
C18 C15 C14 120.4(3) . . ?
O17 C16 O5 122.3(3) . . ?
O17 C16 C14 120.7(3) . . ?
O5 C16 C14 117.0(3) . . ?
O17 C16 Zn1 74.25(19) . 2_655 ?
O5 C16 Zn1 48.04(16) . 2_655 ?
C14 C16 Zn1 164.5(3) . 2_655 ?
C15 C18 C11 120.3(3) . . ?

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
C3 N3 C1 C2 -0.8(5) . . . . ?
Zn1 N3 C1 C2 -179.4(3) 4_465 . . . ?
N3 C1 C2 C13 -1.0(6) . . . . ?
C1 N3 C3 C10 1.6(5) . . . . ?
Zn1 N3 C3 C10 -179.9(3) 4_465 . . . ?
Zn1 O2 C7 O14 -22.6(5) . . . . ?
Zn1 O2 C7 C11 158.6(2) . . . . ?
N3 C3 C10 C13 -0.6(5) . . . . ?
C12 C9A C11 C18 0.1(5) . . . . ?
C12 C9A C11 C7 -178.9(3) . . . . ?
O14 C7 C11 C9A -15.6(4) . . . . ?
O2 C7 C11 C9A 163.3(3) . . . . ?
O14 C7 C11 C18 165.4(3) . . . . ?
O2 C7 C11 C18 -15.8(4) . . . . ?
C11 C9A C12 C14 -5.1(5) . . . . ?
C11 C9A C12 C13 168.6(3) . . . . ?
C3 C10 C13 C2 -1.2(5) . . . . ?
C3 C10 C13 C12 -176.9(3) . . . . ?
C1 C2 C13 C10 1.9(5) . . . . ?
C1 C2 C13 C12 177.9(3) . . . . ?
C9A C12 C13 C10 46.9(5) . . . . ?
C14 C12 C13 C10 -139.5(3) . . . . ?
C9A C12 C13 C2 -128.8(3) . . . . ?
C14 C12 C13 C2 44.8(4) . . . . ?
C9A C12 C14 C15 7.4(5) . . . . ?
C13 C12 C14 C15 -166.4(3) . . . . ?
C9A C12 C14 C16 -168.2(3) . . . . ?
C13 C12 C14 C16 18.1(5) . . . . ?
C12 C14 C15 C18 -4.6(5) . . . . ?
C16 C14 C15 C18 171.1(3) . . . . ?
Zn1 O5 C16 O17 2.1(4) 2_655 . . . ?
Zn1 O5 C16 C14 -174.9(2) 2_655 . . . ?
C15 C14 C16 O17 -131.6(4) . . . . ?
C12 C14 C16 O17 44.0(5) . . . . ?
C15 C14 C16 O5 45.5(5) . . . . ?
C12 C14 C16 O5 -138.9(3) . . . . ?
C15 C14 C16 Zn1 31.1(11) . . . 2_655 ?
C12 C14 C16 Zn1 -153.3(7) . . . 2_655 ?
C14 C15 C18 C11 -0.5(6) . . . . ?
C9A C11 C18 C15 2.8(5) . . . . ?
C7 C11 C18 C15 -178.2(3) . . . . ?

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.102

_shelxl_version_number           2013-2

