# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1507368'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 N2 O5 Zn'
_chemical_formula_weight         309.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
N N 0.0090 0.0050 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0150 0.0080 'Calculated using XDISP in WinGX (Farrugia, 1999)'
Zn Zn 0.1510 1.8620 'Calculated using XDISP in WinGX (Farrugia, 1999)'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.590(3)
_cell_length_b                   11.390(2)
_cell_length_c                   13.990(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1209.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2461
_cell_measurement_theta_min      1
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.82653
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  synchrotron
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14943
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         33.730
_diffrn_reflns_theta_full        29.730
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2771
_reflns_number_gt                2690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.994

_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       'MD2M MAATEL'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond (brandenburg, 1996'
_computing_publication_material  'Platon (Spek, 2009)'

_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)+(0.0682P)²+0.4939P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.080(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2771
_refine_ls_number_parameters     178
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.92407(7) 0.53045(4) 0.58053(3) 0.0328(2) Uani 1 1 d . . . . .
O1 O 1.4048(4) 0.6238(3) 1.0815(2) 0.0369(7) Uani 1 1 d . . . . .
O2 O 1.3414(5) 0.4670(3) 0.9995(2) 0.0415(7) Uani 1 1 d . . . . .
O3 O 0.9149(7) 0.3841(3) 0.9788(3) 0.0579(11) Uani 1 1 d . . . . .
O4 O 0.7724(5) 0.5487(3) 1.0162(3) 0.0422(8) Uani 1 1 d . . . . .
O5 O 0.9454(4) 0.5280(3) 0.7261(2) 0.0350(6) Uani 1 1 d . . . . .
N1 N 0.9409(5) 0.6472(3) 0.8546(3) 0.0320(7) Uani 1 1 d D . . . .
N2 N 0.8613(5) 0.7039(4) 0.6044(3) 0.0345(8) Uani 1 1 d D . . . .
C1 C 1.3069(6) 0.5701(4) 1.0239(3) 0.0327(9) Uani 1 1 d . . . . .
C2 C 1.1499(6) 0.6353(4) 0.9852(3) 0.0348(9) Uani 1 1 d . . . . .
H2A H 1.1929 0.7053 0.9504 0.042 Uiso 1 1 calc R U . . .
H2B H 1.0787 0.6635 1.0399 0.042 Uiso 1 1 calc R U . . .
C3 C 1.0287(5) 0.5652(4) 0.9179(3) 0.0316(8) Uani 1 1 d . . . . .
H3 H 1.1029 0.5112 0.8785 0.038 Uiso 1 1 calc R U . . .
C4 C 0.8953(6) 0.4911(4) 0.9753(3) 0.0324(8) Uani 1 1 d . . . . .
C5 C 0.9100(5) 0.6245(4) 0.7636(3) 0.0306(8) Uani 1 1 d . . . . .
C6 C 0.8165(6) 0.7201(4) 0.7064(3) 0.0321(9) Uani 1 1 d . . . . .
H6 H 0.8531 0.7997 0.7289 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6186(6) 0.7006(4) 0.7238(4) 0.0373(9) Uani 1 1 d . . . . .
H7A H 0.5870 0.6225 0.6978 0.045 Uiso 1 1 calc R U . . .
H7B H 0.5990 0.6976 0.7937 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4911(7) 0.7904(5) 0.6818(4) 0.0432(11) Uani 1 1 d . . . . .
H8 H 0.5114 0.7950 0.6113 0.052 Uiso 1 1 calc R U . . .
C9 C 0.3048(8) 0.7470(7) 0.6989(7) 0.0684(19) Uani 1 1 d . . . . .
H9A H 0.2880 0.7317 0.7673 0.103 Uiso 1 1 calc R U . . .
H9B H 0.2855 0.6744 0.6628 0.103 Uiso 1 1 calc R U . . .
H9C H 0.2206 0.8068 0.6778 0.103 Uiso 1 1 calc R U . . .
C10 C 0.5164(9) 0.9120(5) 0.7241(5) 0.0544(14) Uani 1 1 d . . . . .
H10A H 0.6376 0.9382 0.7127 0.082 Uiso 1 1 calc R U . . .
H10B H 0.4939 0.9094 0.7930 0.082 Uiso 1 1 calc R U . . .
H10C H 0.4342 0.9669 0.6938 0.082 Uiso 1 1 calc R U . . .
H1A H 0.909(8) 0.714(3) 0.871(4) 0.038(14) Uiso 1 1 d D . . . .
H2C H 0.921(6) 0.757(3) 0.587(3) 0.025(11) Uiso 1 1 d D . . . .
H2D H 0.777(8) 0.729(7) 0.576(6) 0.07(2) Uiso 1 1 d 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 O4 1.961(3) 2_664 ?
Zn1 O5 2.043(3) . ?
Zn1 N2 2.060(4) . ?
Zn1 O2 2.110(3) 2_764 ?
Zn1 O1 2.185(3) 2_764 ?
O1 C1 1.255(6) . ?
O1 Zn1 2.185(3) 2_765 ?
O2 C1 1.251(6) . ?
O2 Zn1 2.110(3) 2_765 ?
O3 C4 1.229(6) . ?
O4 C4 1.276(6) . ?
O4 Zn1 1.961(3) 2_665 ?
O5 C5 1.247(5) . ?
N1 C5 1.321(6) . ?
N1 C3 1.449(6) . ?
N2 C6 1.478(6) . ?
C1 C2 1.504(6) . ?
C1 Zn1 2.472(4) 2_765 ?
C2 C3 1.539(6) . ?
C3 C4 1.543(6) . ?
C5 C6 1.526(6) . ?
C6 C7 1.538(6) . ?
C7 C8 1.525(7) . ?
C8 C9 1.517(9) . ?
C8 C10 1.518(8) . ?

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
O4 Zn1 O5 120.74(15) 2_664 . ?
O4 Zn1 N2 109.85(15) 2_664 . ?
O5 Zn1 N2 82.49(14) . . ?
O4 Zn1 O2 113.69(16) 2_664 2_764 ?
O5 Zn1 O2 117.94(14) . 2_764 ?
N2 Zn1 O2 105.60(15) . 2_764 ?
O4 Zn1 O1 94.89(13) 2_664 2_764 ?
O5 Zn1 O1 86.35(12) . 2_764 ?
N2 Zn1 O1 155.21(14) . 2_764 ?
O2 Zn1 O1 60.85(13) 2_764 2_764 ?
C1 O1 Zn1 87.5(3) . 2_765 ?
C1 O2 Zn1 91.0(3) . 2_765 ?
C4 O4 Zn1 121.7(3) . 2_665 ?
C5 O5 Zn1 113.0(3) . . ?
C5 N1 C3 123.0(4) . . ?
C6 N2 Zn1 109.2(3) . . ?
O2 C1 O1 120.6(4) . . ?
O2 C1 C2 122.1(4) . . ?
O1 C1 C2 117.3(4) . . ?
O2 C1 Zn1 58.6(2) . 2_765 ?
O1 C1 Zn1 62.0(2) . 2_765 ?
C2 C1 Zn1 176.5(3) . 2_765 ?
C1 C2 C3 115.9(4) . . ?
N1 C3 C2 108.3(3) . . ?
N1 C3 C4 111.6(3) . . ?
C2 C3 C4 111.0(4) . . ?
O3 C4 O4 125.5(4) . . ?
O3 C4 C3 119.0(4) . . ?
O4 C4 C3 115.6(4) . . ?
O5 C5 N1 122.7(4) . . ?
O5 C5 C6 120.6(4) . . ?
N1 C5 C6 116.6(4) . . ?
N2 C6 C5 108.1(3) . . ?
N2 C6 C7 111.1(4) . . ?
C5 C6 C7 105.6(4) . . ?
C8 C7 C6 117.5(4) . . ?
C9 C8 C10 110.8(5) . . ?
C9 C8 C7 108.2(5) . . ?
C10 C8 C7 112.4(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2C O3 0.793(19) 2.12(2) 2.908(6) 172(5) 4_756
N1 H1A O1 0.83(3) 1.97(3) 2.771(5) 164(6) 3_467
N2 H2C O3 0.793(19) 2.12(2) 2.908(6) 172(5) 4_756
N1 H1A O1 0.83(3) 1.97(3) 2.771(5) 164(6) 3_467

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.129

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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 1507367'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 N2 O5 Zn'
_chemical_formula_weight         309.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
N N 0.0090 0.0050 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0150 0.0080 'Calculated using XDISP in WinGX (Farrugia, 1999)'
Zn Zn 0.1510 1.8620 'Calculated using XDISP in WinGX (Farrugia, 1999)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   5.440(4)
_cell_length_b                   6.0700(10)
_cell_length_c                   19.8000(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.836(11)
_cell_angle_gamma                90
_cell_volume                     651.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1591
_cell_measurement_theta_min      1
_cell_measurement_theta_max      20

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.82656
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  synchrotron
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4111
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         33.693
_diffrn_reflns_theta_full        29.731
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             2548
_reflns_number_gt                2309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_max     0.677
_reflns_Friedel_fraction_full    0.848

_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       'MD2M MAATEL'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond (brandenburg, 1996'
_computing_publication_material  'Platon (Spek, 2009)'


_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)+(0.1187P)²+0.6112P]
 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_abs_structure_details 
;
 Flack x determined using 809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.030(17)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2548
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1895
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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
Zn1A Zn 0.50941(15) 0.17116(19) 0.39602(5) 0.0294(4) Uani 0.9 1 d . . P . .
Zn1B Zn 0.5185(16) 0.2759(14) 0.3549(5) 0.0242(18) Uani 0.1 1 d . . P . .
O1 O 1.2198(12) 0.7561(13) 0.5394(3) 0.0403(16) Uani 1 1 d . . . . .
O2 O 1.4682(11) 0.8978(12) 0.4681(3) 0.0379(15) Uani 1 1 d . . . . .
O3 O 0.6490(12) 0.9686(13) 0.3265(4) 0.0387(17) Uani 1 1 d . . . . .
O4 O 0.5844(14) 0.4313(14) 0.3354(4) 0.0472(19) Uani 1 1 d . . . . .
O5 O 0.2594(13) 0.4397(13) 0.2597(4) 0.0456(17) Uani 1 1 d . . . . .
N1 N 1.1461(12) 1.1395(13) 0.3679(4) 0.0309(16) Uani 1 1 d . . . . .
H1A H 1.0487 1.2071 0.4025 0.037 Uiso 1 1 calc R U . . .
H1B H 1.1053 1.2167 0.3243 0.037 Uiso 1 1 calc R U . . .
N2 N 0.8448(16) 0.7181(15) 0.2688(4) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.9882 0.6684 0.2579 0.051 Uiso 1 1 calc R U . . .
C1 C 1.2632(17) 0.8221(15) 0.4812(5) 0.0333(18) Uani 1 1 d . . . . .
C2 C 1.0500(15) 0.7959(14) 0.4295(5) 0.0337(19) Uani 1 1 d . . . . .
H2A H 0.9025 0.8616 0.4476 0.040 Uiso 1 1 calc R U . . .
H2B H 1.0174 0.6366 0.4229 0.040 Uiso 1 1 calc R U . . .
C3 C 1.0819(15) 0.8995(14) 0.3602(5) 0.0316(18) Uani 1 1 d . . . . .
H3 H 1.2180 0.8217 0.3390 0.038 Uiso 1 1 calc R U . . .
C4 C 0.8389(17) 0.8647(18) 0.3158(5) 0.038(2) Uani 1 1 d . . . . .
C5 C 0.6221(18) 0.6344(19) 0.2339(5) 0.044(3) Uani 1 1 d . . . . .
H5 H 0.5158 0.7611 0.2174 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4759(19) 0.4875(16) 0.2812(5) 0.038(2) Uani 1 1 d . . . . .
C7 C 0.683(2) 0.494(3) 0.1727(6) 0.062(3) Uani 1 1 d . . . . .
H7A H 0.7873 0.3681 0.1893 0.074 Uiso 1 1 calc R U . . .
H7B H 0.5278 0.4329 0.1506 0.074 Uiso 1 1 calc R U . . .
C8 C 0.818(3) 0.620(3) 0.1192(7) 0.081(5) Uani 1 1 d . . . . .
H8 H 0.9676 0.6937 0.1416 0.097 Uiso 1 1 calc R U . . .
C9 C 0.894(5) 0.460(5) 0.0666(9) 0.132(11) Uani 1 1 d . . . . .
H9A H 1.0223 0.3620 0.0870 0.198 Uiso 1 1 calc R U . . .
H9B H 0.9574 0.5419 0.0291 0.198 Uiso 1 1 calc R U . . .
H9C H 0.7504 0.3727 0.0494 0.198 Uiso 1 1 calc R U . . .
C10 C 0.653(5) 0.785(5) 0.0870(11) 0.124(9) Uani 1 1 d . . . . .
H10A H 0.7395 0.8665 0.0535 0.186 Uiso 1 1 calc R U . . .
H10B H 0.6014 0.8870 0.1214 0.186 Uiso 1 1 calc R U . . .
H10C H 0.5078 0.7121 0.0645 0.186 Uiso 1 1 calc R U . . .


_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
Zn1A O1 1.937(7) 2_746 ?
Zn1A N1 2.017(7) 1_445 ?
Zn1A O3 2.039(7) 1_545 ?
Zn1A O4 2.046(8) . ?
Zn1A O2 2.213(7) 1_445 ?
Zn1B O4 1.091(13) . ?
Zn1B O3 2.089(11) 1_545 ?
Zn1B N1 2.224(11) 1_445 ?
Zn1B O1 2.433(12) 2_746 ?
Zn1B O5 2.465(13) . ?
O1 C1 1.261(12) . ?
O2 C1 1.253(11) . ?
O3 C4 1.244(12) . ?
O4 C6 1.228(13) . ?
O5 C6 1.252(13) . ?
N1 C3 1.502(11) . ?
N2 C4 1.290(13) . ?
N2 C5 1.436(13) . ?
C1 C2 1.490(14) . ?
C2 C3 1.531(12) . ?
C3 C4 1.539(13) . ?
C5 C7 1.542(14) . ?
C5 C6 1.559(12) . ?
C7 C8 1.540(18) . ?
C8 C10 1.45(3) . ?
C8 C9 1.51(2) . ?

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 Zn1A N1 151.7(3) 2_746 1_445 ?
O1 Zn1A O3 107.5(3) 2_746 1_545 ?
N1 Zn1A O3 99.7(3) 1_445 1_545 ?
O1 Zn1A O4 90.2(3) 2_746 . ?
N1 Zn1A O4 98.7(3) 1_445 . ?
O3 Zn1A O4 88.0(3) 1_545 . ?
O1 Zn1A O2 83.5(3) 2_746 1_445 ?
N1 Zn1A O2 87.5(3) 1_445 1_445 ?
O3 Zn1A O2 92.7(3) 1_545 1_445 ?
O4 Zn1A O2 173.6(3) . 1_445 ?
O4 Zn1B O3 123.2(8) . 1_545 ?
O4 Zn1B N1 133.8(8) . 1_445 ?
O3 Zn1B N1 91.8(4) 1_545 1_445 ?
O4 Zn1B O1 99.3(7) . 2_746 ?
O3 Zn1B O1 90.0(4) 1_545 2_746 ?
N1 Zn1B O1 110.8(5) 1_445 2_746 ?
O4 Zn1B O5 64.2(7) . . ?
O3 Zn1B O5 109.9(5) 1_545 . ?
N1 Zn1B O5 76.7(4) 1_445 . ?
O1 Zn1B O5 158.9(5) 2_746 . ?
C1 O1 Zn1A 119.8(6) . 2_756 ?
C1 O1 Zn1B 129.0(7) . 2_756 ?
C1 O2 Zn1A 123.3(7) . 1_665 ?
C4 O3 Zn1A 141.5(7) . 1_565 ?
C4 O3 Zn1B 143.5(7) . 1_565 ?
Zn1B O4 C6 113.7(10) . . ?
C6 O4 Zn1A 128.5(7) . . ?
C6 O5 Zn1B 51.2(6) . . ?
C3 N1 Zn1A 109.5(5) . 1_665 ?
C3 N1 Zn1B 123.8(5) . 1_665 ?
C4 N2 C5 121.3(8) . . ?
O2 C1 O1 122.9(10) . . ?
O2 C1 C2 123.4(9) . . ?
O1 C1 C2 113.6(8) . . ?
C1 C2 C3 115.6(7) . . ?
N1 C3 C2 110.5(7) . . ?
N1 C3 C4 111.8(8) . . ?
C2 C3 C4 107.4(7) . . ?
O3 C4 N2 123.0(10) . . ?
O3 C4 C3 121.2(9) . . ?
N2 C4 C3 115.8(8) . . ?
N2 C5 C7 110.2(8) . . ?
N2 C5 C6 111.4(8) . . ?
C7 C5 C6 108.1(9) . . ?
O4 C6 O5 127.0(9) . . ?
O4 C6 C5 116.9(9) . . ?
O5 C6 C5 116.2(9) . . ?
C8 C7 C5 114.3(12) . . ?
C10 C8 C9 109.5(17) . . ?
C10 C8 C7 109.4(14) . . ?
C9 C8 C7 109.2(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.99 1.96 2.907(9) 160.0 2_756
N1 H1B O5 0.99 2.09 2.917(10) 140.3 1_665
N2 H2 O5 0.88 2.02 2.836(11) 153.0 1_655
C2 H2A O1 0.99 2.50 3.239(11) 130.8 2_756
C2 H2A O2 0.99 2.44 3.376(10) 157.2 1_455
C3 H3 O3 1.00 2.54 3.238(10) 126.7 1_655

_refine_diff_density_max         1.609
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.198

_vrf_PLAT341_1                   
;
PROBLEM: Low Bond Precision on  C-C Bonds 
RESPONSE: The analysis of Fo/Fc data for unaccounted
(non)merohedral twinning performed with PLATON/TwinRotMat
routine reveals that no twin law was detected.
This alert may be associated with the fact that
no absorption correction was applied
;
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact O1..O2
RESPONSE: O1 and O2 oxygen atoms belong to the same
deprotonated carboxylate group, and both are coordinated
to Zn1 metal centre. Therefore, no possible H-bond can be establish between O1 and O2 atoms.
;
_vrf_PLAT029_1                   
;
PROBLEM:_diffrn_measured_fraction_theta_full value Low 0.974
RESPONSE: Measurement performed using a single axis rotation diffractometer.
;
_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1507369'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H29 N3 O7 Zn'
_chemical_formula_weight         440.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
N N 0.0110 0.0060 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0180 0.0100 'Calculated using XDISP in WinGX (Farrugia, 1999)'
Zn Zn 0.005 2.145 'Calculated using XDISP in WinGX (Farrugia, 1999)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   8.700(5)
_cell_length_b                   6.200(5)
_cell_length_c                   18.520(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.090(5)
_cell_angle_gamma                90
_cell_volume                     989.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    461
_cell_measurement_theta_min      1
_cell_measurement_theta_max      20

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.89843
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  synchrotron
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5695
_diffrn_reflns_av_unetI/netI     0.6097
_diffrn_reflns_av_R_equivalents  0.3864
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.404
_diffrn_reflns_theta_max         33.926
_diffrn_reflns_theta_full        32.620
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_point_group_measured_fraction_full 0.858
_reflns_number_total             3136
_reflns_number_gt                624
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.714
_reflns_Friedel_fraction_full    0.789

_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       'MD2M MAATEL'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond (brandenburg, 1996'
_computing_publication_material  'Platon (Spek, 2009)'

_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)]
 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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because
 only 2 suitable Friedel pairs available.
;
_refine_ls_abs_structure_Flack   0.04(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2550
_refine_ls_R_factor_gt           0.1483
_refine_ls_wR_factor_ref         0.4284
_refine_ls_wR_factor_gt          0.3049
_refine_ls_goodness_of_fit_ref   0.654
_refine_ls_restrained_S_all      0.654
_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 1.1473(4) 0.8520(6) 0.43850(19) 0.0539(12) Uani 1 1 d . . . . .
O1 O 1.510(3) 1.697(4) 0.4462(15) 0.082(9) Uani 1 1 d . . . . .
O2 O 1.274(2) 1.606(3) 0.4600(12) 0.053(6) Uani 1 1 d . . . . .
O3 O 1.226(3) 0.878(5) 0.3312(14) 0.077(7) Uani 1 1 d . . . . .
O4 O 1.430(2) 0.572(3) 0.2230(11) 0.051(5) Uani 1 1 d . . . . .
O5 O 1.823(3) 1.037(3) 0.3535(12) 0.052(6) Uani 1 1 d . . . . .
O6 O 1.944(3) 0.726(4) 0.3972(13) 0.065(6) Uani 1 1 d . . . . .
N1 N 1.222(3) 1.152(4) 0.4445(16) 0.057(4) Uani 1 1 d . . . . .
H1A H 1.1395 1.2455 0.4592 0.068 Uiso 1 1 calc R U . . .
H1B H 1.3127 1.1616 0.4833 0.068 Uiso 1 1 calc R U . . .
N2 N 1.338(3) 1.111(4) 0.2584(15) 0.057(4) Uani 1 1 d . . . . .
H2N H 1.3742 1.2404 0.2517 0.068 Uiso 1 1 calc R U . . .
N3 N 1.596(3) 0.823(5) 0.2737(13) 0.057(4) Uani 1 1 d . . . . .
H3N H 1.6131 0.9625 0.2769 0.068 Uiso 1 1 calc R U . . .
C1 C 1.414(5) 1.565(6) 0.4345(19) 0.068(11) Uani 1 1 d . . . . .
C2 C 1.412(4) 1.373(7) 0.3896(17) 0.059(8) Uani 1 1 d . . . . .
H2A H 1.4955 1.2772 0.4126 0.071 Uiso 1 1 calc R U . . .
H2B H 1.4407 1.4184 0.3420 0.071 Uiso 1 1 calc R U . . .
C3 C 1.269(3) 1.241(5) 0.3742(14) 0.038(6) Uani 1 1 d . . . . .
H3 H 1.1847 1.3428 0.3540 0.046 Uiso 1 1 calc R U . . .
C4 C 1.271(4) 1.073(5) 0.3206(19) 0.054(8) Uani 1 1 d . . . . .
C5 C 1.350(4) 0.944(5) 0.2028(18) 0.051(8) Uani 1 1 d . . . . .
H5 H 1.2445 0.8837 0.1865 0.061 Uiso 1 1 calc R U . . .
C6 C 1.459(4) 0.755(6) 0.2339(18) 0.056(9) Uani 1 1 d . . . . .
C7 C 1.710(4) 0.686(6) 0.310(2) 0.070(7) Uani 1 1 d . . . . .
H7 H 1.6658 0.5896 0.3446 0.084 Uiso 1 1 calc R U . . .
C8 C 1.837(4) 0.873(8) 0.3558(19) 0.070(7) Uani 1 1 d . . . . .
C9 C 1.793(4) 0.550(6) 0.255(2) 0.080(13) Uani 1 1 d . . . . .
H9A H 1.8471 0.4298 0.2835 0.096 Uiso 1 1 calc R U . . .
H9B H 1.7112 0.4855 0.2195 0.096 Uiso 1 1 calc R U . . .
C10 C 1.899(5) 0.646(6) 0.217(2) 0.085(12) Uani 1 1 d . . . . .
H10 H 1.9810 0.7068 0.2544 0.102 Uiso 1 1 calc R U . . .
C11 C 1.988(6) 0.469(6) 0.172(3) 0.105(17) Uani 1 1 d . . . . .
H11A H 2.0622 0.5437 0.1453 0.158 Uiso 1 1 calc R U . . .
H11B H 1.9112 0.3932 0.1368 0.158 Uiso 1 1 calc R U . . .
H11C H 2.0427 0.3652 0.2058 0.158 Uiso 1 1 calc R U . . .
C12 C 1.840(5) 0.849(11) 0.162(3) 0.118(16) Uani 1 1 d . . . . .
H12A H 1.9267 0.9031 0.1394 0.177 Uiso 1 1 calc R U . . .
H12C H 1.8000 0.9644 0.1907 0.177 Uiso 1 1 calc R U . . .
H12B H 1.7568 0.7994 0.1245 0.177 Uiso 1 1 calc R U . . .
C13 C 1.408(4) 1.037(6) 0.140(2) 0.072(11) Uani 1 1 d . . . . .
H13B H 1.4366 0.9171 0.1096 0.087 Uiso 1 1 calc R U . . .
H13A H 1.5039 1.1169 0.1581 0.087 Uiso 1 1 calc R U . . .
C14 C 1.298(6) 1.194(6) 0.090(2) 0.093(15) Uani 1 1 d . . . . .
H14 H 1.2439 1.2825 0.1236 0.112 Uiso 1 1 calc R U . . .
C15 C 1.171(5) 1.067(10) 0.045(3) 0.13(2) Uani 1 1 d . . . . .
H15C H 1.1203 0.9735 0.0774 0.188 Uiso 1 1 calc R U . . .
H15B H 1.2159 0.9777 0.0096 0.188 Uiso 1 1 calc R U . . .
H15A H 1.0945 1.1659 0.0193 0.188 Uiso 1 1 calc R U . . .
C16 C 1.381(5) 1.354(10) 0.048(3) 0.118(18) Uani 1 1 d . . . . .
H16A H 1.4566 1.4347 0.0817 0.177 Uiso 1 1 calc R U . . .
H16B H 1.3055 1.4548 0.0219 0.177 Uiso 1 1 calc R U . . .
H16C H 1.4349 1.2776 0.0124 0.177 Uiso 1 1 calc R U . . .
O1W O 1.093(2) 0.837(4) 0.5468(10) 0.053(5) 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 1.89(2) 1_545 ?
Zn1 N1 1.97(3) . ?
Zn1 O6 1.99(2) 1_455 ?
Zn1 O1W 2.128(19) . ?
Zn1 O3 2.20(3) . ?
O1 C1 1.17(4) . ?
O2 C1 1.39(4) . ?
O2 Zn1 1.89(2) 1_565 ?
O3 C4 1.29(4) . ?
O4 C6 1.17(4) . ?
O5 C8 1.02(5) . ?
O6 C8 1.44(5) . ?
O6 Zn1 1.99(2) 1_655 ?
N1 C3 1.52(4) . ?
N2 C4 1.38(4) . ?
N2 C5 1.48(4) . ?
N3 C6 1.38(4) . ?
N3 C7 1.40(4) . ?
C1 C2 1.45(5) . ?
C2 C3 1.48(4) . ?
C3 C4 1.44(4) . ?
C5 C13 1.44(5) . ?
C5 C6 1.56(4) . ?
C7 C9 1.56(6) . ?
C7 C8 1.74(5) . ?
C9 C10 1.37(5) . ?
C10 C11 1.63(6) . ?
C10 C12 1.65(7) . ?
C13 C14 1.58(5) . ?
C14 C15 1.50(6) . ?
C14 C16 1.51(6) . ?
O1W O5 2.65(3) 2_846 ?
O1W O6 2.66(3) 2_856 ?

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 N1 125.0(11) 1_545 . ?
O2 Zn1 O6 102.9(10) 1_545 1_455 ?
N1 Zn1 O6 131.5(11) . 1_455 ?
O2 Zn1 O1W 88.1(9) 1_545 . ?
N1 Zn1 O1W 95.9(11) . . ?
O6 Zn1 O1W 92.3(9) 1_455 . ?
O2 Zn1 O3 90.2(10) 1_545 . ?
N1 Zn1 O3 80.7(13) . . ?
O6 Zn1 O3 93.1(10) 1_455 . ?
O1W Zn1 O3 174.5(8) . . ?
C1 O2 Zn1 125.9(19) . 1_565 ?
C4 O3 Zn1 110(2) . . ?
C8 O6 Zn1 115(2) . 1_655 ?
C3 N1 Zn1 114.8(19) . . ?
C4 N2 C5 123(3) . . ?
C6 N3 C7 125(3) . . ?
O1 C1 O2 117(3) . . ?
O1 C1 C2 129(4) . . ?
O2 C1 C2 114(3) . . ?
C1 C2 C3 121(3) . . ?
C4 C3 C2 116(3) . . ?
C4 C3 N1 111(2) . . ?
C2 C3 N1 111(2) . . ?
O3 C4 N2 117(3) . . ?
O3 C4 C3 123(3) . . ?
N2 C4 C3 120(3) . . ?
C13 C5 N2 110(2) . . ?
C13 C5 C6 110(3) . . ?
N2 C5 C6 112(3) . . ?
O4 C6 N3 122(3) . . ?
O4 C6 C5 124(3) . . ?
N3 C6 C5 114(3) . . ?
N3 C7 C9 113(3) . . ?
N3 C7 C8 101(3) . . ?
C9 C7 C8 111(3) . . ?
O5 C8 O6 136(4) . . ?
O5 C8 C7 125(3) . . ?
O6 C8 C7 99(3) . . ?
C10 C9 C7 120(4) . . ?
C9 C10 C11 112(4) . . ?
C9 C10 C12 118(4) . . ?
C11 C10 C12 109(4) . . ?
C5 C13 C14 118(3) . . ?
C15 C14 C16 116(4) . . ?
C15 C14 C13 110(4) . . ?
C16 C14 C13 115(4) . . ?
Zn1 O1W O5 127.5(10) . 2_846 ?
Zn1 O1W O6 112.6(12) . 2_856 ?
O5 O1W O6 113.7(9) 2_846 2_856 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1W 0.99 2.09 2.99(4) 151.7 2_756
N1 H1B O1 0.99 1.89 2.87(4) 175.9 2_846
N2 H2N O4 0.88 2.19 3.07(3) 170.7 1_565
N3 H3N O5 0.88 2.20 2.65(3) 111.6 .
C2 H2B O4 0.99 2.39 3.35(4) 162.0 1_565
C7 H7 O1 1.00 2.55 3.27(5) 128.2 1_545
C9 H9B O4 0.99 2.51 3.13(4) 120.6 .

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.132

_vrf_RINTA01_3                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Several crystals were measured and the best crystal
was investigated
and it was still weakly diffracting.
Moreover, the low data completeness
is attributed to the data collection
having been performed with only omega scan
;
_vrf_PLAT020_3                   
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: see RINTA01_3
;
_vrf_PLAT026_3                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low
RESPONSE: see RINTA01_3
;
_vrf_PLAT029_3                   
;
PROBLEM:_diffrn_measured_fraction_theta_full value Low
RESPONSE: see RINTA01_3
;
_vrf_PLAT234_3                   
;
PROBLEM: Large Hirshfeld Difference C14--C15
RESPONSE: see RINTA01_3
;
_vrf_PLAT084_3                   
;
PROBLEM: High wR2 Value (i.e. > 0.25)
High wR2 Value (i.e. > 0.25)
;
_vrf_PLAT041_3                   
;
PROBLEM: Calc. and Reported SumFormula Strings Differ 
RESPONSE: It was impossible to localize the H atoms
of the coordinated water molecule; but they were
included in the formula
;
_vrf_PLAT043_3                   
;
PROBLEM: Calculated and Reported Mol. Weight Differ by 1.99
RESPONSE: see PLAT041_3
;

_shelxl_version_number           2013-2

