# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_zn
_database_code_depnum_ccdc_archive 'CCDC 1538368'
_audit_update_record             
;
2017-03-15 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N O5 Zn'
_chemical_formula_weight         324.58

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.4729(5)
_cell_length_b                   7.8274(3)
_cell_length_c                   12.5069(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.642(4)
_cell_angle_gamma                90.00
_cell_volume                     1181.40(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2152
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      25.35

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    2.098
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.5532
_exptl_absorpt_correction_T_max  0.7301
_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            7637
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2152
_reflns_number_gt                1611
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0244P)²+0.0164P] 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         2152
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.33719(3) 0.31677(5) 0.69077(4) 0.03025(17) Uani 1 1 d . . .
O2 O 0.47962(19) 0.4654(4) 0.7458(2) 0.0414(7) Uani 1 1 d . . .
N1 N 0.3201(2) 0.4995(3) 0.5614(2) 0.0289(7) Uani 1 1 d . . .
O3 O -0.18279(19) 0.6746(4) 0.3053(2) 0.0410(7) Uani 1 1 d . . .
O1 O 0.5871(2) 0.6535(3) 0.6864(2) 0.0391(7) Uani 1 1 d . . .
O1W O 0.3486(2) 0.1238(3) 0.5815(2) 0.0476(8) Uani 1 1 d . . .
H1WA H 0.3938 0.0487 0.6149 0.071 Uiso 1 1 d R . .
H1WB H 0.3719 0.1653 0.5289 0.071 Uiso 1 1 d R . .
C6 C 0.2367(3) 0.5193(5) 0.4711(3) 0.0316(9) Uani 1 1 d . . .
H6 H 0.1736 0.4528 0.4641 0.038 Uiso 1 1 calc R . .
C4 C 0.3344(3) 0.7322(4) 0.4002(3) 0.0339(10) Uani 1 1 d . . .
H4 H 0.3396 0.8109 0.3460 0.041 Uiso 1 1 calc R . .
C8 C 0.1664(3) 0.6634(5) 0.1840(3) 0.0377(10) Uani 1 1 d . . .
H8 H 0.2389 0.6711 0.1777 0.045 Uiso 1 1 calc R . .
C3 C 0.4210(3) 0.7134(5) 0.4933(3) 0.0352(10) Uani 1 1 d . . .
H3 H 0.4850 0.7786 0.5026 0.042 Uiso 1 1 calc R . .
C9 C 0.0800(3) 0.6694(5) 0.0906(3) 0.0407(10) Uani 1 1 d . . .
H9 H 0.0948 0.6802 0.0217 0.049 Uiso 1 1 calc R . .
C11 C -0.0508(3) 0.6454(4) 0.2005(3) 0.0290(9) Uani 1 1 d . . .
C13 C -0.1684(3) 0.6400(5) 0.2107(4) 0.0348(10) Uani 1 1 d . . .
C7 C 0.1462(3) 0.6460(4) 0.2875(3) 0.0286(9) Uani 1 1 d . . .
C2 C 0.4105(3) 0.5965(4) 0.5717(3) 0.0279(9) Uani 1 1 d . . .
C10 C -0.0277(3) 0.6597(4) 0.0979(3) 0.0368(10) Uani 1 1 d . . .
H10 H -0.0854 0.6626 0.0341 0.044 Uiso 1 1 calc R . .
O4 O -0.2450(2) 0.6038(4) 0.1297(2) 0.0492(8) Uani 1 1 d . . .
C12 C 0.0368(3) 0.6382(4) 0.2950(3) 0.0277(9) Uani 1 1 d . . .
H12 H 0.0220 0.6280 0.3640 0.033 Uiso 1 1 calc R . .
C5 C 0.2397(3) 0.6333(4) 0.3878(3) 0.0291(9) Uani 1 1 d . . .
C1 C 0.4998(3) 0.5694(5) 0.6770(3) 0.0326(9) 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 O3 1.940(2) 3_566 ?
Zn1 O1 2.038(2) 2_646 ?
Zn1 O1W 2.066(3) . ?
Zn1 O2 2.089(2) . ?
Zn1 N1 2.130(3) . ?
O2 C1 1.255(4) . ?
N1 C6 1.337(4) . ?
N1 C2 1.338(4) . ?
O3 C13 1.269(4) . ?
O3 Zn1 1.940(2) 3_566 ?
O1 C1 1.252(4) . ?
O1 Zn1 2.038(2) 2_656 ?
O1W H1WA 0.8473 . ?
O1W H1WB 0.8478 . ?
C6 C5 1.380(5) . ?
C6 H6 0.9300 . ?
C4 C3 1.381(5) . ?
C4 C5 1.388(5) . ?
C4 H4 0.9300 . ?
C8 C9 1.375(5) . ?
C8 C7 1.387(5) . ?
C8 H8 0.9300 . ?
C3 C2 1.371(5) . ?
C3 H3 0.9300 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9300 . ?
C11 C10 1.389(5) . ?
C11 C12 1.393(5) . ?
C11 C13 1.505(5) . ?
C13 O4 1.237(4) . ?
C7 C12 1.393(5) . ?
C7 C5 1.484(5) . ?
C2 C1 1.510(5) . ?
C10 H10 0.9300 . ?
C12 H12 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
O3 Zn1 O1 106.07(11) 3_566 2_646 ?
O3 Zn1 O1W 106.11(12) 3_566 . ?
O1 Zn1 O1W 86.77(11) 2_646 . ?
O3 Zn1 O2 137.64(12) 3_566 . ?
O1 Zn1 O2 84.68(11) 2_646 . ?
O1W Zn1 O2 115.46(10) . . ?
O3 Zn1 N1 94.98(11) 3_566 . ?
O1 Zn1 N1 158.79(10) 2_646 . ?
O1W Zn1 N1 89.92(11) . . ?
O2 Zn1 N1 77.86(11) . . ?
C1 O2 Zn1 115.9(2) . . ?
C6 N1 C2 118.2(3) . . ?
C6 N1 Zn1 128.8(2) . . ?
C2 N1 Zn1 112.8(2) . . ?
C13 O3 Zn1 113.9(2) . 3_566 ?
C1 O1 Zn1 128.9(2) . 2_656 ?
Zn1 O1W H1WA 109.2 . . ?
Zn1 O1W H1WB 109.1 . . ?
H1WA O1W H1WB 109.4 . . ?
N1 C6 C5 123.3(3) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 C13 121.0(4) . . ?
C12 C11 C13 120.0(4) . . ?
O4 C13 O3 123.5(4) . . ?
O4 C13 C11 120.3(4) . . ?
O3 C13 C11 116.3(3) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C5 120.4(3) . . ?
C12 C7 C5 121.0(3) . . ?
N1 C2 C3 122.7(3) . . ?
N1 C2 C1 115.0(3) . . ?
C3 C2 C1 122.3(3) . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C7 C12 C11 120.9(4) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 C7 121.1(3) . . ?
C4 C5 C7 121.5(3) . . ?
O1 C1 O2 126.6(4) . . ?
O1 C1 C2 116.1(4) . . ?
O2 C1 C2 117.2(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
O3 Zn1 O2 C1 -94.3(3) 3_566 . . . ?
O1 Zn1 O2 C1 157.7(3) 2_646 . . . ?
O1W Zn1 O2 C1 73.8(3) . . . . ?
N1 Zn1 O2 C1 -10.2(2) . . . . ?
O3 Zn1 N1 C6 -39.1(3) 3_566 . . . ?
O1 Zn1 N1 C6 147.8(3) 2_646 . . . ?
O1W Zn1 N1 C6 67.0(3) . . . . ?
O2 Zn1 N1 C6 -176.9(3) . . . . ?
O3 Zn1 N1 C2 146.0(2) 3_566 . . . ?
O1 Zn1 N1 C2 -27.0(4) 2_646 . . . ?
O1W Zn1 N1 C2 -107.8(2) . . . . ?
O2 Zn1 N1 C2 8.3(2) . . . . ?
C2 N1 C6 C5 0.6(5) . . . . ?
Zn1 N1 C6 C5 -174.0(2) . . . . ?
C5 C4 C3 C2 -0.2(6) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
Zn1 O3 C13 O4 -4.5(5) 3_566 . . . ?
Zn1 O3 C13 C11 175.3(2) 3_566 . . . ?
C10 C11 C13 O4 18.8(5) . . . . ?
C12 C11 C13 O4 -162.0(3) . . . . ?
C10 C11 C13 O3 -161.0(3) . . . . ?
C12 C11 C13 O3 18.2(5) . . . . ?
C9 C8 C7 C12 -1.3(6) . . . . ?
C9 C8 C7 C5 177.8(3) . . . . ?
C6 N1 C2 C3 -0.5(5) . . . . ?
Zn1 N1 C2 C3 174.9(3) . . . . ?
C6 N1 C2 C1 178.7(3) . . . . ?
Zn1 N1 C2 C1 -5.9(4) . . . . ?
C4 C3 C2 N1 0.3(5) . . . . ?
C4 C3 C2 C1 -178.8(3) . . . . ?
C8 C9 C10 C11 0.7(6) . . . . ?
C12 C11 C10 C9 -1.1(5) . . . . ?
C13 C11 C10 C9 178.1(3) . . . . ?
C8 C7 C12 C11 0.8(5) . . . . ?
C5 C7 C12 C11 -178.2(3) . . . . ?
C10 C11 C12 C7 0.4(5) . . . . ?
C13 C11 C12 C7 -178.9(3) . . . . ?
N1 C6 C5 C4 -0.5(5) . . . . ?
N1 C6 C5 C7 178.0(3) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C3 C4 C5 C7 -178.2(3) . . . . ?
C8 C7 C5 C6 -138.5(4) . . . . ?
C12 C7 C5 C6 40.5(5) . . . . ?
C8 C7 C5 C4 39.8(5) . . . . ?
C12 C7 C5 C4 -141.1(4) . . . . ?
Zn1 O1 C1 O2 -56.0(5) 2_656 . . . ?
Zn1 O1 C1 C2 124.1(3) 2_656 . . . ?
Zn1 O2 C1 O1 -169.6(3) . . . . ?
Zn1 O2 C1 C2 10.2(4) . . . . ?
N1 C2 C1 O1 177.1(3) . . . . ?
C3 C2 C1 O1 -3.7(5) . . . . ?
N1 C2 C1 O2 -2.7(5) . . . . ?
C3 C2 C1 O2 176.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.082
﻿####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 1538369'
_audit_update_record             
;
2017-03-15 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N O5 Zn'
_chemical_formula_weight         324.60

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           Trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   31.2060(7)
_cell_length_b                   31.2060(7)
_cell_length_c                   10.5025(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     8857.3(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3493
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      25.10

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2951
_exptl_absorpt_coefficient_mu    1.259
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7868
_exptl_absorpt_correction_T_max  0.8636
_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            7320
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3493
_reflns_number_gt                2841
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1000P)²+0.0000P] 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         3493
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_restrained_S_all      0.862
_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 -0.017432(12) 0.315599(12) 0.18922(3) 0.02481(16) Uani 1 1 d . . .
O1 O -0.03936(9) 0.21252(8) -0.0869(2) 0.0503(7) Uani 1 1 d . . .
O1W O -0.07952(8) 0.31028(8) 0.08231(19) 0.0355(5) Uani 1 1 d . . .
H1 H -0.0849 0.3321 0.1213 0.043 Uiso 1 1 d R . .
H2 H -0.0744 0.3162 0.0118 0.043 Uiso 1 1 d R . .
O2 O -0.00675(7) 0.28476(7) 0.01688(16) 0.0263(5) Uani 1 1 d . . .
O3 O -0.27841(7) 0.02514(7) 0.51736(18) 0.0296(5) Uani 1 1 d . . .
O4 O -0.27371(7) 0.04312(7) 0.72451(18) 0.0326(5) Uani 1 1 d . . .
N1 N -0.05980(9) 0.23919(9) 0.2262(2) 0.0276(6) Uani 1 1 d . . .
C1 C -0.03528(11) 0.23768(11) 0.0078(3) 0.0308(7) Uani 1 1 d . . .
C2 C -0.06521(12) 0.21149(11) 0.1241(3) 0.0329(7) Uani 1 1 d . . .
C3 C -0.09648(14) 0.16066(12) 0.1260(3) 0.0510(10) Uani 1 1 d . . .
H2A H -0.1014 0.1420 0.0528 0.061 Uiso 1 1 calc R . .
C4 C -0.12020(14) 0.13819(12) 0.2379(3) 0.0511(10) Uani 1 1 d . . .
H3 H -0.1419 0.1042 0.2401 0.061 Uiso 1 1 calc R . .
C5 C -0.11170(11) 0.16624(11) 0.3469(3) 0.0336(7) Uani 1 1 d . . .
C6 C -0.08198(11) 0.21737(11) 0.3349(3) 0.0319(7) Uani 1 1 d . . .
H5 H -0.0774 0.2371 0.4057 0.038 Uiso 1 1 calc R . .
C7 C -0.13250(11) 0.14345(11) 0.4725(3) 0.0315(7) Uani 1 1 d . . .
C8 C -0.18145(11) 0.10626(11) 0.4841(3) 0.0288(7) Uani 1 1 d . . .
H8 H -0.2013 0.0947 0.4120 0.035 Uiso 1 1 calc R . .
C9 C -0.20112(11) 0.08602(10) 0.6028(3) 0.0266(6) Uani 1 1 d . . .
C10 C -0.17094(12) 0.10245(12) 0.7094(3) 0.0355(7) Uani 1 1 d . . .
H11 H -0.1837 0.0889 0.7888 0.043 Uiso 1 1 calc R . .
C11 C -0.12187(12) 0.13907(13) 0.6978(3) 0.0439(9) Uani 1 1 d . . .
H9 H -0.1015 0.1496 0.7692 0.053 Uiso 1 1 calc R . .
C12 C -0.10322(12) 0.15988(12) 0.5811(3) 0.0401(8) Uani 1 1 d . . .
H10 H -0.0705 0.1853 0.5746 0.048 Uiso 1 1 calc R . .
C13 C -0.25494(10) 0.04864(10) 0.6164(3) 0.0252(6) 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 O3 2.036(2) 18 ?
Zn1 O4 2.0786(19) 11_556 ?
Zn1 N1 2.105(2) . ?
Zn1 O2 2.1457(18) 6_455 ?
Zn1 O2 2.1528(18) . ?
Zn1 O1W 2.173(2) . ?
O1 C1 1.234(3) . ?
O1W H1 0.8788 . ?
O1W H2 0.7608 . ?
O2 C1 1.285(3) . ?
O2 Zn1 2.1456(18) 8_554 ?
O3 C13 1.272(3) . ?
O3 Zn1 2.0363(19) 17_445 ?
O4 C13 1.250(3) . ?
O4 Zn1 2.0786(19) 12_556 ?
N1 C2 1.334(4) . ?
N1 C6 1.333(3) . ?
C1 C2 1.506(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.379(4) . ?
C3 H2A 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H3 0.9300 . ?
C5 C6 1.394(4) . ?
C5 C7 1.485(4) . ?
C6 H5 0.9300 . ?
C7 C8 1.387(4) . ?
C7 C12 1.389(4) . ?
C8 C9 1.393(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(4) . ?
C9 C13 1.498(4) . ?
C10 C11 1.384(4) . ?
C10 H11 0.9300 . ?
C11 C12 1.373(4) . ?
C11 H9 0.9300 . ?
C12 H10 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
O3 Zn1 O4 85.65(8) 18 11_556 ?
O3 Zn1 N1 173.77(9) 18 . ?
O4 Zn1 N1 89.48(9) 11_556 . ?
O3 Zn1 O2 87.35(8) 18 6_455 ?
O4 Zn1 O2 97.53(7) 11_556 6_455 ?
N1 Zn1 O2 97.15(8) . 6_455 ?
O3 Zn1 O2 97.88(7) 18 . ?
O4 Zn1 O2 91.85(8) 11_556 . ?
N1 Zn1 O2 78.38(8) . . ?
O2 Zn1 O2 169.60(5) 6_455 . ?
O3 Zn1 O1W 95.72(8) 18 . ?
O4 Zn1 O1W 173.94(8) 11_556 . ?
N1 Zn1 O1W 88.73(9) . . ?
O2 Zn1 O1W 88.44(7) 6_455 . ?
O2 Zn1 O1W 82.12(7) . . ?
Zn1 O1W H1 102.1 . . ?
Zn1 O1W H2 114.3 . . ?
H1 O1W H2 111.3 . . ?
C1 O2 Zn1 123.44(17) . 8_554 ?
C1 O2 Zn1 113.56(17) . . ?
Zn1 O2 Zn1 115.12(9) 8_554 . ?
C13 O3 Zn1 126.93(18) . 17_445 ?
C13 O4 Zn1 131.63(19) . 12_556 ?
C2 N1 C6 119.5(3) . . ?
C2 N1 Zn1 112.97(18) . . ?
C6 N1 Zn1 127.5(2) . . ?
O1 C1 O2 125.4(3) . . ?
O1 C1 C2 118.0(3) . . ?
O2 C1 C2 116.6(2) . . ?
N1 C2 C3 121.3(3) . . ?
N1 C2 C1 117.2(3) . . ?
C3 C2 C1 121.5(3) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H2A 120.5 . . ?
C2 C3 H2A 120.5 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H3 120.0 . . ?
C5 C4 H3 120.0 . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 C7 122.2(3) . . ?
C6 C5 C7 120.7(3) . . ?
N1 C6 C5 122.7(3) . . ?
N1 C6 H5 118.6 . . ?
C5 C6 H5 118.6 . . ?
C8 C7 C12 118.9(3) . . ?
C8 C7 C5 120.9(3) . . ?
C12 C7 C5 120.2(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 C13 120.1(3) . . ?
C8 C9 C13 120.5(3) . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H11 120.0 . . ?
C11 C10 H11 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H9 120.0 . . ?
C10 C11 H9 120.0 . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H10 119.6 . . ?
C7 C12 H10 119.6 . . ?
O4 C13 O3 124.6(3) . . ?
O4 C13 C9 117.4(2) . . ?
O3 C13 C9 118.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.059

# start Validation Reply Form
_vrf_PLAT602_1                   
;
PROBLEM: A VERY LARGE Solvent Accessible VOID(S) in Structure ! Info
RESPONSE: In this compound, there is a larger 1D channel and no any guest molecules are included. Moreover, we don't treat it through Sqweeze
;
# end Validation Reply Form
