# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_p4nnc-1
_database_code_depnum_ccdc_archive 'CCDC 1020282'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4.36 N3.36 O3 Zn'
_chemical_formula_weight         236.92

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           ?
_symmetry_space_group_name_H-M   P4/ncc

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

_cell_length_a                   13.4537(9)
_cell_length_b                   13.4537(9)
_cell_length_c                   27.329(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4946.6(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1886
_exptl_absorpt_coefficient_mu    1.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6490
_exptl_absorpt_correction_T_max  0.6939
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26236
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2280
_reflns_number_gt                1727
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1005P)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     SHELXL
_refine_ls_extinction_coef       0.00013(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2280
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.007 0.203 0.250 951 185 ' '
2 0.008 0.294 0.750 951 185 ' '

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
O1 O 0.4454(3) 0.1386(3) 0.36757(12) 0.0625(10) Uani 1 1 d . . .
Zn1 Zn 0.52227(3) 0.08925(3) 0.446728(16) 0.0297(2) Uani 1 1 d . . .
N3 N 0.5142(3) 0.2329(3) 0.46533(13) 0.0359(8) Uani 1 1 d . . .
O2 O 0.5751(3) 0.0449(3) 0.38345(13) 0.0613(11) Uani 1 1 d . . .
C1 C 0.5162(4) 0.0846(4) 0.35307(19) 0.0543(15) Uani 1 1 d . . .
C2 C 0.5322(4) 0.0677(4) 0.29987(19) 0.0566(14) Uani 1 1 d . A .
C3 C 0.4792(5) 0.1205(5) 0.26433(18) 0.0685(17) Uani 1 1 d . . .
H3 H 0.4311 0.1665 0.2735 0.082 Uiso 0.639(18) 1 calc PR A 1
N4 N 0.4061(11) 0.1818(13) 0.2761(4) 0.097(8) Uani 0.361(18) 1 d P A 2
H4A H 0.3718 0.2102 0.2535 0.116 Uiso 0.361(18) 1 calc PR A 2
H4B H 0.3928 0.1932 0.3064 0.116 Uiso 0.361(18) 1 calc PR A 2
C4 C 0.6035(5) -0.0010(5) 0.28475(19) 0.0676(17) Uani 1 1 d . . .
H4 H 0.6407 -0.0344 0.3082 0.081 Uiso 1 1 calc R A .
N1 N 0.3922(2) 0.0255(3) 0.46578(13) 0.0339(8) Uani 1 1 d . . .
N2 N 0.6243(3) 0.0375(2) 0.49562(12) 0.0324(8) Uani 1 1 d . . .
C5 C 0.4633(3) 0.3063(3) 0.44389(15) 0.0390(11) Uani 1 1 d . . .
H5 H 0.4240 0.2973 0.4163 0.047 Uiso 1 1 calc R . .
C6 C 0.5602(3) 0.2807(3) 0.50279(15) 0.0391(10) Uani 1 1 d . . .
O4 O 0.2500 0.2500 0.3522(5) 0.184(6) Uani 1 4 d S . .
H6 H 0.620(5) 0.259(5) 0.530(2) 0.11(2) Uiso 1 1 d . . .
O6 O 0.2500 0.2500 0.1811(9) 0.264(10) Uani 1 4 d S . .
O3 O 0.7500 0.2500 0.5782(3) 0.130(3) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.082(2) 0.074(2) 0.0307(18) -0.0087(17) 0.0163(18) 0.004(2)
Zn1 0.0340(3) 0.0317(3) 0.0233(3) 0.00101(17) -0.00099(19) -0.0007(2)
N3 0.042(2) 0.0335(19) 0.0325(18) -0.0020(16) -0.0056(15) 0.0009(15)
O2 0.081(3) 0.080(3) 0.0223(18) -0.0030(17) 0.0011(17) 0.007(2)
C1 0.077(4) 0.057(3) 0.030(3) -0.002(2) 0.011(3) -0.013(3)
C2 0.075(4) 0.069(3) 0.026(3) -0.012(2) 0.004(2) 0.004(3)
C3 0.086(4) 0.088(4) 0.032(3) -0.007(3) 0.004(3) 0.034(4)
N4 0.119(15) 0.137(15) 0.035(8) -0.004(7) -0.007(7) 0.089(12)
C4 0.090(4) 0.083(4) 0.030(3) 0.002(3) -0.005(3) 0.021(4)
N1 0.0314(18) 0.043(2) 0.0272(17) 0.0077(15) -0.0031(15) -0.0031(15)
N2 0.0311(18) 0.0388(19) 0.0273(18) 0.0047(14) -0.0026(15) -0.0014(15)
C5 0.048(3) 0.037(2) 0.032(2) -0.0060(18) -0.0133(19) 0.003(2)
C6 0.047(2) 0.036(2) 0.034(2) -0.003(2) -0.011(2) 0.000(2)
O4 0.191(9) 0.191(9) 0.170(15) 0.000 0.000 0.000
O6 0.275(16) 0.275(16) 0.24(2) 0.000 0.000 0.000
O3 0.124(7) 0.118(6) 0.149(7) 0.000 0.000 0.030(5)

_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
O1 C1 1.261(6) . ?
O1 Zn1 2.488(4) . ?
Zn1 O2 1.963(4) . ?
Zn1 N3 2.002(3) . ?
Zn1 N1 2.017(3) . ?
Zn1 N2 2.038(3) . ?
N3 C5 1.337(5) . ?
N3 C6 1.357(5) . ?
O2 C1 1.266(7) . ?
C1 C2 1.487(7) . ?
C2 C4 1.394(8) . ?
C2 C3 1.399(8) . ?
C3 N4 1.324(13) . ?
C3 C4 1.387(7) 7_545 ?
C4 C3 1.387(7) 7_545 ?
N1 C5 1.310(5) 4 ?
N1 N2 1.372(5) 9_656 ?
N2 C6 1.315(5) 12_656 ?
N2 N1 1.372(5) 9_656 ?
C5 N1 1.310(5) 3 ?
C6 N2 1.315(5) 11_666 ?

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
C1 O1 Zn1 78.8(3) . . ?
O2 Zn1 N3 122.50(16) . . ?
O2 Zn1 N1 114.33(15) . . ?
N3 Zn1 N1 107.34(15) . . ?
O2 Zn1 N2 103.30(15) . . ?
N3 Zn1 N2 101.53(14) . . ?
N1 Zn1 N2 105.65(14) . . ?
O2 Zn1 O1 57.69(15) . . ?
N3 Zn1 O1 86.60(13) . . ?
N1 Zn1 O1 88.69(13) . . ?
N2 Zn1 O1 160.24(13) . . ?
C5 N3 C6 102.4(3) . . ?
C5 N3 Zn1 129.0(3) . . ?
C6 N3 Zn1 128.6(3) . . ?
C1 O2 Zn1 102.9(3) . . ?
O1 C1 O2 120.6(5) . . ?
O1 C1 C2 120.3(5) . . ?
O2 C1 C2 119.0(5) . . ?
C4 C2 C3 118.8(5) . . ?
C4 C2 C1 119.4(5) . . ?
C3 C2 C1 121.8(5) . . ?
N4 C3 C4 118.8(7) . 7_545 ?
N4 C3 C2 121.7(7) . . ?
C4 C3 C2 119.3(5) 7_545 . ?
C3 C4 C2 121.9(5) 7_545 . ?
C5 N1 N2 106.2(3) 4 9_656 ?
C5 N1 Zn1 126.8(3) 4 . ?
N2 N1 Zn1 127.0(3) 9_656 . ?
C6 N2 N1 106.0(3) 12_656 9_656 ?
C6 N2 Zn1 126.7(3) 12_656 . ?
N1 N2 Zn1 127.3(3) 9_656 . ?
N1 C5 N3 113.1(4) 3 . ?
N2 C6 N3 112.3(4) 11_666 . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.551
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.100
