# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_NUS-5
_database_code_depnum_ccdc_archive 'CCDC 1045563'
_audit_update_record             
;
2015-04-17 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H2 N2 O3 Zn'
_chemical_formula_weight         191.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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                   8.8126(3)
_cell_length_b                   10.6094(3)
_cell_length_c                   10.5394(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.180(3)
_cell_angle_gamma                90
_cell_volume                     979.67(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2328
_cell_measurement_theta_min      4.1500
_cell_measurement_theta_max      73.0600

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.229
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_T_min  0.88274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3635
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.935
_diffrn_reflns_theta_max         73.670
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1908
_reflns_number_gt                1767
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0378P)²+1.1007P] 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_number_reflns         1908
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.016 0.428 -0.025 434 130 ' '
_platon_squeeze_details          
;
Large sections of the structure, 449.1 cubic Angstrom or 45.8% of 
the unit cell volume, consist of solvent filled voids. The content 
of the voids is partially recognizable as mostly disordered 
dimethylacetamide, isopropanol, and some water molecules, while 
other sections show only featureless electron density. Attempts 
to include solvent molecules in the structural model yielded less 
than satisfactory results. The data were thus instead corrected for 
using back Fourier transform methods as implemented in the Squeeze 
algorithm of the Platon program package. Correction for unresolved 
electron density yielded 130 electrons for the void volume.
;

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 0.81496(3) 0.42688(3) 0.48894(3) 0.01049(12) Uani 1 1 d . . . . .
O3 O 0.66780(19) 0.48369(17) 0.34493(16) 0.0204(4) Uani 1 1 d . . . . .
O1 O 0.7177(2) 0.77428(16) 0.90673(16) 0.0190(4) Uani 1 1 d . . . . .
O2 O 0.91973(19) 0.89353(16) 0.89552(16) 0.0189(4) Uani 1 1 d . . . . .
N1 N 0.8765(2) 0.56846(18) 0.60635(19) 0.0132(4) Uani 1 1 d . . . . .
N2 N 1.0145(2) 0.62944(19) 0.60889(18) 0.0138(4) Uani 1 1 d . . . . .
C1 C 0.7991(3) 0.6208(2) 0.6950(2) 0.0151(5) Uani 1 1 d . . . . .
H1 H 0.7003 0.5958 0.7133 0.018 Uiso 1 1 calc R U . . .
C4 C 0.8413(3) 0.7999(2) 0.8578(2) 0.0136(4) Uani 1 1 d . . . . .
C2 C 0.8848(3) 0.7177(2) 0.7565(2) 0.0130(4) Uani 1 1 d . . . . .
C3 C 1.0193(3) 0.7190(2) 0.6978(2) 0.0157(5) Uani 1 1 d . . . . .
H3 H 1.1020 0.7755 0.7181 0.019 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
Zn1 O3 1.9811(17) . ?
Zn1 N1 1.9843(19) . ?
Zn1 O1 1.9953(16) 2_646 ?
Zn1 N2 2.0031(19) 3_766 ?
O1 C4 1.284(3) . ?
O1 Zn1 1.9953(16) 2_656 ?
O2 C4 1.250(3) . ?
N1 C1 1.335(3) . ?
N1 N2 1.375(3) . ?
N2 C3 1.332(3) . ?
N2 Zn1 2.0031(19) 3_766 ?
C1 C2 1.393(3) . ?
C4 C2 1.461(3) . ?
C2 C3 1.395(3) . ?

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 N1 111.10(8) . . ?
O3 Zn1 O1 123.21(8) . 2_646 ?
N1 Zn1 O1 108.45(8) . 2_646 ?
O3 Zn1 N2 99.32(8) . 3_766 ?
N1 Zn1 N2 112.14(8) . 3_766 ?
O1 Zn1 N2 101.67(7) 2_646 3_766 ?
C4 O1 Zn1 103.20(14) . 2_656 ?
C1 N1 N2 107.92(19) . . ?
C1 N1 Zn1 128.70(16) . . ?
N2 N1 Zn1 123.37(14) . . ?
C3 N2 N1 108.09(18) . . ?
C3 N2 Zn1 127.31(16) . 3_766 ?
N1 N2 Zn1 124.10(15) . 3_766 ?
N1 C1 C2 109.9(2) . . ?
O2 C4 O1 120.3(2) . . ?
O2 C4 C2 121.8(2) . . ?
O1 C4 C2 117.9(2) . . ?
C1 C2 C3 104.14(19) . . ?
C1 C2 C4 127.5(2) . . ?
C3 C2 C4 128.3(2) . . ?
N2 C3 C2 109.9(2) . . ?

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.083

_shelxl_version_number           2014-3



