# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_MOF1
_database_code_depnum_ccdc_archive 'CCDC 1868716'
loop_
_audit_author_name
_audit_author_address
'Sandeep Singh Dhankhar'
;IIT Ropar
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT306_MOF1                
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O1W Check
RESPONSE: As a guest water molecule, the H atoms of O1w are not located. 
;
_vrf_PLAT306_MOF1_2              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O2W Check
RESPONSE: As a guest water molecule, the H atoms of O2w are not located. 
;
_vrf_PLAT306_MOF1_3              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O3W Check
RESPONSE: As a guest water molecule, the H atoms of O3w are not located. 
;
_vrf_PLAT306_MOF1_4              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O4W Check
RESPONSE: As a guest water molecule, the H atoms of O4w are not located. 
;
_vrf_PLAT430_MOF1                
;
PROBLEM: Short Inter D...A Contact  O1W      ..O4W      .       2.80 Ang.
RESPONSE: The alerts are due to the potential strong hydrogen-bonding interactions among guest water molecules and coordinated water molecules. But it is mainly also due to the no adding hydrogen atoms of the guest water molecules Oxygen.
;
_vrf_PLAT430_MOF1_2              
;
PROBLEM: Short Inter D...A Contact  O1W      ..O4W      .       2.81 Ang.
RESPONSE: The alerts are due to the potential strong hydrogen-bonding interactions among guest water molecules and coordinated water molecules. But it is mainly also due to the no adding hydrogen atoms of the guest water molecules Oxygen.
;
_vrf_PLAT430_MOF1_3              
;
PROBLEM: Short Inter D...A Contact  O2W      ..O4       .       2.80 Ang.
RESPONSE: The alerts are due to the potential strong hydrogen-bonding interactions among guest water molecules and coordinated water molecules. But it is mainly also due to the no adding hydrogen atoms of the guest water molecules Oxygen 
;
_vrf_PLAT430_MOF1_4              
;
PROBLEM: Short Inter D...A Contact  O3       ..O3W      .       2.74 Ang.
RESPONSE: The alerts are due to the potential strong hydrogen-bonding interactions among guest water molecules and coordinated water molecules. But it is mainly also due to the no adding hydrogen atoms of the guest water molecules Oxygen. 
;
# Added during the CSD deposition process: Thursday 20 September 2018 05:25 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H11 N2 O7 Zn, 4(O)'
_chemical_formula_sum            'C21 H11 N2 O11 Zn'
_chemical_formula_weight         532.69

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                   4.821(5)
_cell_length_b                   17.325(5)
_cell_length_c                   27.459(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.618(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2293(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5711
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      28.3

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.135
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6853
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83821
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.351
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5711
_reflns_number_gt                4669
_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       'APEX2 (Bruker, 2014.3)'
_computing_cell_refinement       'APEX2 (Bruker, 2014.3);SAINT (Bruker, 2014)'
_computing_data_reduction        'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'WinGX(Farrugia, 2013)'

_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)+(0.0616P)²+1.9795P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5711
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_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 0.70136(6) 0.94346(2) 0.29976(2) 0.03006(10) Uani 1 1 d . . . . .
C20 C 0.1091(5) 0.98305(17) 0.43445(8) 0.0382(6) Uani 1 1 d . . . . .
C16 C 0.3926(6) 1.03389(16) 0.37212(10) 0.0429(6) Uani 1 1 d . . . . .
H16 H 0.4609 1.0766 0.3558 0.051 Uiso 1 1 calc R U . . .
O6 O 1.6395(4) 1.00036(12) 0.15098(6) 0.0464(5) Uani 1 1 d . . . . .
O5 O 1.0325(5) 1.16338(14) 0.07526(7) 0.0653(7) Uani 1 1 d . . . . .
O1 O 0.8506(4) 0.84240(10) 0.31492(7) 0.0443(4) Uani 1 1 d . . . . .
N2 N 1.3589(4) 1.08721(12) 0.11206(6) 0.0324(4) Uani 1 1 d . . . . .
O3 O 0.8448(5) 1.12265(12) 0.30739(7) 0.0547(6) Uani 1 1 d . . . . .
C8 C 1.4684(5) 1.01704(13) 0.02263(7) 0.0284(4) Uani 1 1 d . . . . .
O2 O 0.9633(4) 1.01270(10) 0.27203(7) 0.0443(4) Uani 1 1 d . . . . .
O7 O 0.4345(4) 0.94036(14) 0.24355(8) 0.0577(6) Uani 1 1 d . . . . .
C1 C 0.9559(5) 0.80912(14) 0.27868(9) 0.0364(5) Uani 1 1 d . . . . .
C9 C 1.2723(5) 1.07722(14) 0.02395(8) 0.0330(5) Uani 1 1 d . . . . .
C19 C 0.2112(6) 1.04565(17) 0.40944(10) 0.0467(7) Uani 1 1 d . . . . .
H19 H 0.1580 1.0954 0.4177 0.056 Uiso 1 1 calc R U . . .
O4 O 0.9509(5) 0.83663(12) 0.23729(8) 0.0618(6) Uani 1 1 d . . . . .
C5 C 1.3168(5) 1.12641(13) 0.15821(8) 0.0316(5) Uani 1 1 d . . . . .
N1 N 0.4738(4) 0.96393(12) 0.35851(7) 0.0327(4) Uani 1 1 d . . . . .
C15 C 1.1604(5) 1.09087(14) 0.19278(8) 0.0318(5) Uani 1 1 d . . . . .
H15 H 1.0785 1.0432 0.1864 0.038 Uiso 1 1 calc R U . . .
C14 C 1.1258(5) 1.12704(13) 0.23756(8) 0.0296(5) Uani 1 1 d . . . . .
C10 C 1.2073(6) 1.11340(15) 0.07118(8) 0.0384(6) Uani 1 1 d . . . . .
C3 C 1.0580(5) 0.69667(14) 0.33328(8) 0.0339(5) Uani 1 1 d . . . . .
C11 C 1.1402(6) 1.10204(16) -0.01828(9) 0.0419(6) Uani 1 1 d . . . . .
C7 C 1.6039(5) 0.98944(13) 0.06536(8) 0.0306(5) Uani 1 1 d . . . . .
C13 C 0.9615(5) 1.08689(14) 0.27579(8) 0.0329(5) Uani 1 1 d . . . . .
C6 C 1.5399(5) 1.02435(14) 0.11278(8) 0.0320(5) Uani 1 1 d . . . . .
C21 C -0.0824(6) 0.9938(2) 0.47622(10) 0.0471(7) Uani 1 1 d . . . . .
C2 C 1.0917(5) 0.73293(13) 0.28870(8) 0.0314(5) Uani 1 1 d . . . . .
C4 C 1.2525(5) 0.69835(13) 0.25355(8) 0.0315(5) Uani 1 1 d . . . . .
C18 C 0.1957(6) 0.91088(18) 0.42049(10) 0.0478(7) Uani 1 1 d . . . . .
H18 H 0.1320 0.8673 0.4365 0.057 Uiso 1 1 calc R U . . .
C17 C 0.3766(6) 0.90307(16) 0.38286(10) 0.0436(6) Uani 1 1 d . . . . .
H17 H 0.4332 0.8538 0.3740 0.052 Uiso 1 1 calc R U . . .
C12 C 1.7955(6) 0.93095(15) 0.06339(9) 0.0392(6) Uani 1 1 d . . . . .
O3W O 0.8022(7) 1.2543(2) 0.36183(15) 0.1148(13) Uani 1 1 d . . . . .
O4W O 0.7536(8) 0.2004(2) 0.46151(16) 0.1226(13) Uani 1 1 d . . . . .
O2W O 0.1959(9) 0.8438(3) 0.14632(13) 0.1278(15) Uani 1 1 d . . . . .
O1W O 0.2636(8) 0.2182(2) 0.51243(14) 0.1125(12) Uani 1 1 d . . . . .
H4 H 1.279(5) 0.7232(15) 0.2252(10) 0.032(7) Uiso 1 1 d . . . . .
H3 H 0.953(5) 0.7211(16) 0.3580(10) 0.036(7) Uiso 1 1 d . . . . .
H12 H 1.887(6) 0.9196(17) 0.0916(11) 0.040(7) Uiso 1 1 d . . . . .
H11 H 1.008(7) 1.1387(19) -0.0171(11) 0.050(9) Uiso 1 1 d . . . . .
H21A H -0.194(9) 0.947(2) 0.4797(15) 0.071(12) Uiso 1 1 d . . . . .
H21B H -0.183(9) 1.038(3) 0.4702(17) 0.087(14) Uiso 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 1.915(2) . ?
Zn1 O1 1.9339(18) . ?
Zn1 O7 1.982(2) . ?
Zn1 N1 2.008(2) . ?
C20 C18 1.376(4) . ?
C20 C19 1.382(4) . ?
C20 C21 1.504(3) . ?
C16 N1 1.330(3) . ?
C16 C19 1.381(4) . ?
O6 C6 1.215(3) . ?
O5 C10 1.216(3) . ?
O1 C1 1.268(3) . ?
N2 C6 1.395(3) . ?
N2 C10 1.398(3) . ?
N2 C5 1.457(3) . ?
O3 C13 1.217(3) . ?
C8 C9 1.409(3) . ?
C8 C7 1.410(3) . ?
C8 C8 1.417(4) 3_875 ?
O2 C13 1.290(3) . ?
C1 O4 1.232(3) . ?
C1 C2 1.496(3) . ?
C9 C11 1.376(3) . ?
C9 C10 1.482(3) . ?
C5 C15 1.375(3) . ?
C5 C3 1.376(3) 2_755 ?
N1 C17 1.340(3) . ?
C15 C14 1.394(3) . ?
C14 C4 1.387(3) 2_755 ?
C14 C13 1.504(3) . ?
C3 C5 1.376(3) 2_745 ?
C3 C2 1.390(3) . ?
C11 C12 1.407(3) 3_875 ?
C7 C12 1.373(4) . ?
C7 C6 1.476(3) . ?
C21 C21 1.524(6) 3_576 ?
C2 C4 1.390(3) . ?
C4 C14 1.387(3) 2_745 ?
C18 C17 1.377(4) . ?
C12 C11 1.407(3) 3_875 ?

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 O1 114.03(10) . . ?
O2 Zn1 O7 97.36(10) . . ?
O1 Zn1 O7 111.87(10) . . ?
O2 Zn1 N1 126.17(9) . . ?
O1 Zn1 N1 101.26(8) . . ?
O7 Zn1 N1 105.85(11) . . ?
C18 C20 C19 117.4(2) . . ?
C18 C20 C21 121.5(3) . . ?
C19 C20 C21 121.1(3) . . ?
N1 C16 C19 122.7(3) . . ?
C1 O1 Zn1 113.42(15) . . ?
C6 N2 C10 125.27(19) . . ?
C6 N2 C5 116.99(19) . . ?
C10 N2 C5 117.7(2) . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 C8 119.5(3) . 3_875 ?
C7 C8 C8 118.8(3) . 3_875 ?
C13 O2 Zn1 125.91(16) . . ?
O4 C1 O1 123.4(2) . . ?
O4 C1 C2 120.5(2) . . ?
O1 C1 C2 116.1(2) . . ?
C11 C9 C8 120.3(2) . . ?
C11 C9 C10 120.1(2) . . ?
C8 C9 C10 119.6(2) . . ?
C16 C19 C20 119.7(3) . . ?
C15 C5 C3 121.7(2) . 2_755 ?
C15 C5 N2 119.0(2) . . ?
C3 C5 N2 119.3(2) 2_755 . ?
C16 N1 C17 117.8(2) . . ?
C16 N1 Zn1 123.92(17) . . ?
C17 N1 Zn1 117.94(17) . . ?
C5 C15 C14 119.3(2) . . ?
C4 C14 C15 119.7(2) 2_755 . ?
C4 C14 C13 121.2(2) 2_755 . ?
C15 C14 C13 119.1(2) . . ?
O5 C10 N2 120.4(2) . . ?
O5 C10 C9 123.1(2) . . ?
N2 C10 C9 116.5(2) . . ?
C5 C3 C2 119.2(2) 2_745 . ?
C9 C11 C12 120.5(2) . 3_875 ?
C12 C7 C8 120.9(2) . . ?
C12 C7 C6 119.6(2) . . ?
C8 C7 C6 119.4(2) . . ?
O3 C13 O2 124.7(2) . . ?
O3 C13 C14 121.7(2) . . ?
O2 C13 C14 113.6(2) . . ?
O6 C6 N2 120.7(2) . . ?
O6 C6 C7 122.3(2) . . ?
N2 C6 C7 116.96(19) . . ?
C20 C21 C21 110.8(3) . 3_576 ?
C3 C2 C4 119.9(2) . . ?
C3 C2 C1 120.0(2) . . ?
C4 C2 C1 120.1(2) . . ?
C14 C4 C2 120.2(2) 2_745 . ?
C20 C18 C17 120.1(3) . . ?
N1 C17 C18 122.3(3) . . ?
C7 C12 C11 120.0(2) . 3_875 ?

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_MOF2
_database_code_depnum_ccdc_archive 'CCDC 1868717'
loop_
_audit_author_name
_audit_author_address
'Sandeep Singh Dhankhar'
;IIT Ropar
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_MOF2                
;
PROBLEM: Check Calcd Resid. Dens.  2.86A   From O2              3.85 eA-3
RESPONSE: These alerts are due to disorder in guest solvent molecules nearby and q peaks are not assigned to any element.
;
_vrf_PLAT094_MOF2                
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       7.33 Report
RESPONSE: These alerts are due to disorder in guest solvent molecules. The alert was mainly due to absorbance around Zn(II) atom. 
;
_vrf_PLAT097_MOF2                
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.93 eA-3
RESPONSE: These alerts are due to disorder in guest solvent molecules. The alert was mainly due to absorbance around Zn(II) atom. 
;
_vrf_PLAT306_MOF2                
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O1W Check
RESPONSE: As a guest molecule, the H atoms of O1w are not located.
;
_vrf_PLAT306_MOF2_2              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O2W Check
RESPONSE: As a guest molecule, the H atoms of O2w are not located.
;
_vrf_PLAT306_MOF2_3              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O3W Check
RESPONSE: As a guest molecule, the H atoms of  O3w are not located.
;
_vrf_PLAT601_MOF2                
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        145 Ang**3
RESPONSE: These alerts are due to disorder in guest solvent molecules. The alert was mainly due to there is q peak that not assigned to any element.
;
# Added during the CSD deposition process: Thursday 20 September 2018 05:34 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H15 N3 O6 Zn, 3(O)'
_chemical_formula_sum            'C27 H15 N3 O9 Zn'
_chemical_formula_weight         590.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

_cell_length_a                   10.082(5)
_cell_length_b                   13.637(5)
_cell_length_c                   20.120(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 97.575(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2742.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6875
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.4

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.953
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            113172
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.527
_diffrn_reflns_theta_max         28.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6875
_reflns_number_gt                5317
_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       'APEX2 (Bruker, 2014.3)'
_computing_cell_refinement       'APEX2 (Bruker, 2014.3);SAINT (Bruker, 2014)'
_computing_data_reduction        'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'WinGX(Farrugia, 2013)'

_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)+(0.1457P)²+6.1734P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6875
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2462
_refine_ls_wR_factor_gt          0.2297
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_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 0.63453(4) 0.78731(3) 0.68435(2) 0.02242(18) Uani 1 1 d . . . . .
O2 O 0.8511(3) 0.7891(2) 0.68737(17) 0.0389(8) Uani 1 1 d . . . . .
O1 O 0.7393(3) 0.7834(3) 0.58708(19) 0.0442(9) Uani 1 1 d . . . . .
C24 C 0.6130(5) 1.1461(4) 0.6681(3) 0.0490(13) Uani 1 1 d . . . . .
N1 N 0.6345(4) 0.6301(3) 0.6907(2) 0.0400(9) Uani 1 1 d . . . . .
O3 O 0.4549(3) 0.7829(2) 0.62251(16) 0.0333(7) Uani 1 1 d . . . . .
O6 O 1.0765(5) 0.9588(3) 0.42659(17) 0.0583(11) Uani 1 1 d . . . . .
N3 N 1.0800(4) 0.7925(3) 0.42542(18) 0.0331(8) Uani 1 1 d . . . . .
C3 C 1.0998(4) 0.7889(3) 0.63587(19) 0.0252(8) Uani 1 1 d . . . . .
H3 H 1.1032 0.7892 0.6823 0.030 Uiso 1 1 calc R U . . .
N2 N 0.6258(4) 0.9429(3) 0.68046(19) 0.0330(8) Uani 1 1 d . . . . .
O4 O 0.6476(3) 0.7949(2) 0.78734(15) 0.0381(8) Uani 1 1 d . . . . .
O5 O 1.0790(6) 0.6271(3) 0.42519(19) 0.0716(14) Uani 1 1 d . . . . .
C19 C 0.6378(5) 0.4260(4) 0.6968(3) 0.0499(13) Uani 1 1 d . . . . .
C2 C 0.9771(4) 0.7880(3) 0.5956(2) 0.0289(8) Uani 1 1 d . . . . .
C7 C 1.0912(5) 0.7910(3) 0.4980(2) 0.0337(10) Uani 1 1 d . . . . .
C4 C 0.9737(4) 0.7891(3) 0.5260(2) 0.0333(10) Uani 1 1 d . . . . .
H4 H 0.8919 0.7886 0.4985 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2132(4) 0.7901(3) 0.5371(2) 0.0290(9) Uani 1 1 d . . . . .
H6 H 0.2917 0.7900 0.5175 0.035 Uiso 1 1 calc R U . . .
C11 C 1.0154(4) 0.7934(3) 0.2857(2) 0.0281(8) Uani 1 1 d . . . . .
C5 C 0.2181(4) 0.7893(3) 0.60702(19) 0.0241(8) Uani 1 1 d . . . . .
C12 C 1.0315(5) 0.7029(3) 0.3195(2) 0.0334(9) Uani 1 1 d . . . . .
C27 C 0.3513(4) 0.7888(3) 0.65131(19) 0.0222(7) Uani 1 1 d . . . . .
C10 C 1.0301(4) 0.8831(3) 0.3199(2) 0.0306(9) Uani 1 1 d . . . . .
C1 C 0.8481(4) 0.7863(3) 0.6248(2) 0.0315(9) Uani 1 1 d . . . . .
C20 C 0.6642(5) 1.0000(4) 0.7325(3) 0.0445(11) Uani 1 1 d . . . . .
H20 H 0.6960 0.9711 0.7734 0.053 Uiso 1 1 calc R U . . .
C23 C 0.6586(6) 1.1019(4) 0.7283(4) 0.0561(15) Uani 1 1 d . . . . .
H23 H 0.6855 1.1400 0.7660 0.067 Uiso 1 1 calc R U . . .
C13 C 1.0153(5) 0.6161(4) 0.2849(2) 0.0393(10) Uani 1 1 d . . . . .
O2W O 0.6627(9) 0.6564(6) 0.4756(3) 0.138(3) Uani 1 1 d . . . . .
O3W O 0.7473(7) 0.7828(5) 0.3767(3) 0.104(2) Uani 1 1 d . . . . .
C25 C 0.6034(7) 1.2539(5) 0.6585(4) 0.0604(15) Uani 1 1 d . . . . .
H25 H 0.5676 1.2773 0.6165 0.072 Uiso 1 1 calc R U . . .
C22 C 0.5741(7) 1.0876(4) 0.6141(3) 0.0606(15) Uani 1 1 d . . . . .
H22 H 0.5444 1.1150 0.5725 0.073 Uiso 1 1 calc R U . . .
C14 C 1.0148(5) 0.9701(3) 0.2853(2) 0.0350(9) Uani 1 1 d . . . . .
C21 C 0.5794(7) 0.9869(4) 0.6221(3) 0.0539(14) Uani 1 1 d . . . . .
H21 H 0.5495 0.9477 0.5853 0.065 Uiso 1 1 calc R U . . .
C18 C 0.5842(7) 0.4760(4) 0.6383(4) 0.0640(17) Uani 1 1 d . . . . .
H18 H 0.5488 0.4412 0.6003 0.077 Uiso 1 1 calc R U . . .
C15 C 0.6835(6) 0.5822(4) 0.7464(3) 0.0497(13) Uani 1 1 d . . . . .
H15 H 0.7175 0.6185 0.7840 0.060 Uiso 1 1 calc R U . . .
C8 C 1.0649(5) 0.7022(4) 0.3936(2) 0.0393(11) Uani 1 1 d . . . . .
C17 C 0.6859(7) 0.4815(4) 0.7507(4) 0.0598(15) Uani 1 1 d . . . . .
H17 H 0.7206 0.4514 0.7907 0.072 Uiso 1 1 calc R U . . .
C9 C 1.0629(5) 0.8837(4) 0.3937(2) 0.0349(9) Uani 1 1 d . . . . .
C16 C 0.5846(6) 0.5773(4) 0.6378(3) 0.0517(13) Uani 1 1 d . . . . .
H16 H 0.5486 0.6098 0.5989 0.062 Uiso 1 1 calc R U . . .
C26 C 0.6417(7) 1.3170(5) 0.7049(4) 0.0614(16) Uani 1 1 d . . . . .
H26 H 0.6746 1.2926 0.7470 0.074 Uiso 1 1 calc R U . . .
O1W O 0.7367(11) 0.9553(7) 0.4631(7) 0.231(7) Uani 1 1 d . . . . .
H13 H 1.007(6) 0.560(5) 0.309(3) 0.058(18) Uiso 1 1 d . . . . .
H14 H 1.017(5) 1.030(4) 0.314(3) 0.042(14) Uiso 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 2.059(3) . ?
Zn1 O4 2.061(3) . ?
Zn1 N2 2.124(4) . ?
Zn1 N1 2.147(4) . ?
Zn1 O2 2.176(4) . ?
Zn1 O1 2.344(4) . ?
Zn1 C1 2.599(4) . ?
O2 C1 1.256(6) . ?
O1 C1 1.249(6) . ?
C24 C22 1.363(9) . ?
C24 C23 1.376(9) . ?
C24 C25 1.484(8) . ?
N1 C16 1.328(7) . ?
N1 C15 1.334(7) . ?
O3 C27 1.262(5) . ?
O6 C9 1.217(6) . ?
N3 C8 1.388(6) . ?
N3 C9 1.398(6) . ?
N3 C7 1.450(5) . ?
C3 C2 1.387(6) . ?
C3 C5 1.394(5) 1_655 ?
N2 C20 1.322(6) . ?
N2 C21 1.347(7) . ?
O4 C27 1.236(5) 2_656 ?
O5 C8 1.203(6) . ?
C19 C17 1.358(9) . ?
C19 C18 1.405(9) . ?
C19 C26 1.495(9) 1_545 ?
C2 C4 1.395(6) . ?
C2 C1 1.497(6) . ?
C7 C6 1.369(6) 1_655 ?
C7 C4 1.378(6) . ?
C6 C7 1.369(6) 1_455 ?
C6 C5 1.400(5) . ?
C11 C10 1.401(6) . ?
C11 C12 1.409(6) . ?
C11 C11 1.428(8) 2_755 ?
C5 C3 1.394(5) 1_455 ?
C5 C27 1.511(5) . ?
C12 C13 1.372(6) . ?
C12 C8 1.484(6) . ?
C27 O4 1.236(5) 2_656 ?
C10 C14 1.373(6) . ?
C10 C9 1.479(6) . ?
C20 C23 1.393(8) . ?
C13 C13 1.397(9) 2_755 ?
C25 C26 1.292(10) . ?
C22 C21 1.382(8) . ?
C14 C14 1.414(8) 2_755 ?
C18 C16 1.382(8) . ?
C15 C17 1.376(7) . ?
C26 C19 1.495(9) 1_565 ?

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 122.93(13) . . ?
O3 Zn1 N2 88.76(13) . . ?
O4 Zn1 N2 89.08(14) . . ?
O3 Zn1 N1 89.98(14) . . ?
O4 Zn1 N1 89.46(15) . . ?
N2 Zn1 N1 177.15(15) . . ?
O3 Zn1 O2 144.76(13) . . ?
O4 Zn1 O2 92.31(13) . . ?
N2 Zn1 O2 91.51(13) . . ?
N1 Zn1 O2 91.00(13) . . ?
O3 Zn1 O1 87.26(13) . . ?
O4 Zn1 O1 149.79(13) . . ?
N2 Zn1 O1 90.73(13) . . ?
N1 Zn1 O1 91.76(14) . . ?
O2 Zn1 O1 57.49(12) . . ?
O3 Zn1 C1 115.94(14) . . ?
O4 Zn1 C1 121.12(14) . . ?
N2 Zn1 C1 91.21(13) . . ?
N1 Zn1 C1 91.64(14) . . ?
O2 Zn1 C1 28.81(14) . . ?
O1 Zn1 C1 28.68(14) . . ?
C1 O2 Zn1 94.6(3) . . ?
C1 O1 Zn1 87.1(3) . . ?
C22 C24 C23 118.2(5) . . ?
C22 C24 C25 117.9(6) . . ?
C23 C24 C25 123.9(6) . . ?
C16 N1 C15 117.8(5) . . ?
C16 N1 Zn1 119.8(4) . . ?
C15 N1 Zn1 122.4(3) . . ?
C27 O3 Zn1 115.9(3) . . ?
C8 N3 C9 125.4(4) . . ?
C8 N3 C7 116.2(4) . . ?
C9 N3 C7 117.5(4) . . ?
C2 C3 C5 120.2(4) . 1_655 ?
C20 N2 C21 117.4(4) . . ?
C20 N2 Zn1 123.6(3) . . ?
C21 N2 Zn1 119.1(3) . . ?
C27 O4 Zn1 172.6(3) 2_656 . ?
C17 C19 C18 117.1(5) . . ?
C17 C19 C26 117.8(6) . 1_545 ?
C18 C19 C26 125.1(6) . 1_545 ?
C3 C2 C4 119.3(4) . . ?
C3 C2 C1 121.7(4) . . ?
C4 C2 C1 119.1(4) . . ?
C6 C7 C4 121.3(4) 1_655 . ?
C6 C7 N3 121.6(4) 1_655 . ?
C4 C7 N3 117.1(4) . . ?
C7 C4 C2 120.1(4) . . ?
C7 C6 C5 119.2(4) 1_455 . ?
C10 C11 C12 122.0(4) . . ?
C10 C11 C11 119.3(2) . 2_755 ?
C12 C11 C11 118.8(2) . 2_755 ?
C3 C5 C6 119.9(4) 1_455 . ?
C3 C5 C27 119.8(3) 1_455 . ?
C6 C5 C27 120.2(3) . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 C8 120.0(4) . . ?
C11 C12 C8 119.2(4) . . ?
O4 C27 O3 124.3(4) 2_656 . ?
O4 C27 C5 118.6(4) 2_656 . ?
O3 C27 C5 117.0(3) . . ?
C14 C10 C11 120.5(4) . . ?
C14 C10 C9 119.9(4) . . ?
C11 C10 C9 119.6(4) . . ?
O1 C1 O2 120.9(4) . . ?
O1 C1 C2 120.1(4) . . ?
O2 C1 C2 119.1(4) . . ?
O1 C1 Zn1 64.3(2) . . ?
O2 C1 Zn1 56.6(2) . . ?
C2 C1 Zn1 175.5(3) . . ?
N2 C20 C23 122.3(5) . . ?
C24 C23 C20 119.8(6) . . ?
C12 C13 C13 120.4(3) . 2_755 ?
C26 C25 C24 123.9(7) . . ?
C24 C22 C21 119.1(6) . . ?
C10 C14 C14 120.2(2) . 2_755 ?
N2 C21 C22 123.2(6) . . ?
C16 C18 C19 119.3(6) . . ?
N1 C15 C17 122.9(6) . . ?
O5 C8 N3 120.8(4) . . ?
O5 C8 C12 122.2(5) . . ?
N3 C8 C12 117.0(4) . . ?
C19 C17 C15 120.3(6) . . ?
O6 C9 N3 120.1(4) . . ?
O6 C9 C10 123.1(4) . . ?
N3 C9 C10 116.8(4) . . ?
N1 C16 C18 122.5(6) . . ?
C25 C26 C19 125.7(8) . 1_565 ?

_refine_diff_density_max         3.935
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.150

_shelxl_version_number           2014-3



