# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1506975'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_audit_creation_date             2016-08-02
_audit_creation_method           'by CrystalStructure 4.2'




# start Validation Reply Form
_vrf_RINTA01_3                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Small poor quality crystals.
;
_vrf_PLAT020_3                   
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.282 Report
RESPONSE: Small poor quality crystals.
;


_chemical_formula_sum            'C6 H4 Co N6 O4'
_chemical_formula_moiety         'C6 H4 Co N6 O4'
_chemical_formula_weight         283.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        I41/amd
_space_group_name_Hall           '-I 4bd 2'
_space_group_IT_number           141
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y+1/2, z'
'y+1/4, x+1/4, z+3/4'
'y+1/4, -x+1/4, z+3/4'
'-x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+3/4'
'-y+3/4, -x+1/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'y+3/4, x+3/4, z+5/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+5/4'
'-y+5/4, -x+3/4, z+5/4'
'-x, -y, -z'
'-x, y-1/2, -z'
'-y-1/4, -x-1/4, -z-3/4'
'-y-1/4, x-1/4, -z-3/4'
'x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-3/4'
'y-3/4, x-1/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y, -z+1/2'
'-y+1/4, -x+1/4, -z-1/4'
'-y+1/4, x+1/4, -z-1/4'
'x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z-1/4'
'y-1/4, x+1/4, -z-1/4'
#------------------------------------------------------------------------------
_cell_length_a                   6.025(18)
_cell_length_b                   6.025(18)
_cell_length_c                   26.95(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     978(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    375
_cell_measurement_theta_min      7.53
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564.00
_exptl_absorpt_coefficient_mu    13.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.091
_exptl_absorpt_correction_T_max  0.657

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            6242
_diffrn_reflns_av_R_equivalents  0.2823
_diffrn_reflns_theta_max         67.645
_diffrn_reflns_theta_min         6.571
_diffrn_reflns_theta_full        67.645
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             273
_reflns_number_gt                223
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0977
_refine_ls_wR_factor_ref         0.2973
_refine_ls_wR_factor_gt          0.2787
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         273
_refine_ls_number_parameters     30
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1570P)²+2.8079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0027(16)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Co Co -2.3653 3.6143
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Co1 Co 0.0000 0.7500 0.1250 0.081(2) Uani 1 8 d S T P . .
O1 O 0.6805(16) 0.7500 0.1942(3) 0.084(3) Uani 1 2 d S T P . .
N1 N 0.5000 0.7500 0.1727(5) 0.073(4) Uani 1 4 d S T P . .
N3 N 0.3103(17) 0.7500 0.0946(3) 0.069(3) Uani 1 2 d S T P . .
C2 C 0.5000 0.7500 0.1200(6) 0.065(4) Uani 1 4 d S T P . .
C4 C 0.387(2) 0.7500 0.0466(4) 0.072(3) Uani 1 2 d S T P . .
H4 H 0.2964 0.7500 0.0177 0.086 Uiso 1 2 calc R U P . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Co1 N3 2.042(11) . ?
Co1 N3 2.042(11) 5 ?
Co1 N3 2.042(11) 20_666 ?
Co1 N3 2.042(11) 19_666 ?
O1 N1 1.232(11) . ?
N1 O1 1.232(11) 5_655 ?
N1 C2 1.42(2) . ?
N3 C2 1.333(12) . ?
N3 C4 1.375(15) . ?
C2 N3 1.333(12) 5_655 ?
C4 C4 1.36(3) 5_655 ?
C4 H4 0.9500 . ?

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
N3 Co1 N3 132.6(5) . 5 ?
N3 Co1 N3 99.29(19) . 20_666 ?
N3 Co1 N3 99.29(19) 5 20_666 ?
N3 Co1 N3 99.29(19) . 19_666 ?
N3 Co1 N3 99.29(19) 5 19_666 ?
N3 Co1 N3 132.6(5) 20_666 19_666 ?
O1 N1 O1 123.9(13) 5_655 . ?
O1 N1 C2 118.0(7) 5_655 . ?
O1 N1 C2 118.0(7) . . ?
C2 N3 C4 101.3(10) . . ?
C2 N3 Co1 125.4(7) . . ?
C4 N3 Co1 133.4(8) . . ?
N3 C2 N3 118.1(13) . 5_655 ?
N3 C2 N1 120.9(7) . . ?
N3 C2 N1 121.0(7) 5_655 . ?
C4 C4 N3 109.7(7) 5_655 . ?
C4 C4 H4 125.2 5_655 . ?
N3 C4 H4 125.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N3 C2 N3 0.000(0) . . . 5_655 ?
Co1 N3 C2 N3 180.000(1) . . . 5_655 ?
C4 N3 C2 N1 180.000(0) . . . . ?
Co1 N3 C2 N1 0.000(1) . . . . ?
O1 N1 C2 N3 0.000(1) 5_655 . . . ?
O1 N1 C2 N3 180.000(1) . . . . ?
O1 N1 C2 N3 180.000(1) 5_655 . . 5_655 ?
O1 N1 C2 N3 0.000(1) . . . 5_655 ?
C2 N3 C4 C4 0.000(1) . . . 5_655 ?
Co1 N3 C4 C4 180.000(1) . . . 5_655 ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
####################################################################### 
# 
# 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 1506974'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N6 O4 Zn'
_chemical_formula_sum            'C6 H4 N6 O4 Zn'
_chemical_formula_weight         289.52

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        Pccn
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   8.462(8)
_cell_length_b                   14.549(15)
_cell_length_c                   18.799(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2314(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1897
_cell_measurement_theta_min      21.2
_cell_measurement_theta_max      68.7

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 22.2222
_diffrn_reflns_number            26196
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0976
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.705
_diffrn_reflns_theta_max         68.086
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2059
_reflns_number_gt                1913
_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       
; 
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009) 
;
_computing_cell_refinement       
; 
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009) 
;
_computing_data_reduction        
; 
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
In the structure, the crystallographically-imposed symmetry results in
 positional disorder in two of the three nitroimidazolates.  Multiple
 restraints to bond distances and angles, as well as enhanced rigid-bond
 restraints were required to successfully model these nitroimidazolates.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+14.1440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2059
_refine_ls_number_parameters     219
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0942
_refine_ls_wR_factor_ref         0.2008
_refine_ls_wR_factor_gt          0.1976
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_restrained_S_all      1.388
_refine_ls_shift/su_max          0.002
_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 0.88751(13) 0.06121(7) 0.85522(5) 0.0458(4) Uani 1 1 d . . . . .
O1 O 1.0521(8) -0.0975(4) 0.8361(3) 0.0651(18) Uani 1 1 d . . . . .
O2 O 1.2234(9) -0.1455(4) 0.7599(3) 0.0683(19) Uani 1 1 d . . . . .
N1 N 1.0518(9) 0.0720(4) 0.7757(3) 0.0477(16) Uani 1 1 d . . . . .
N2 N 1.2274(9) 0.0223(4) 0.6955(3) 0.0517(17) Uani 1 1 d . . . . .
N3 N 1.1387(9) -0.0864(5) 0.7847(3) 0.0513(17) Uani 1 1 d . . . . .
C1 C 1.1415(10) 0.0040(5) 0.7523(4) 0.0467(19) Uani 1 1 d . . . . .
C2 C 1.0846(12) 0.1412(5) 0.7314(4) 0.056(2) Uani 1 1 d . . . . .
H2B H 1.0394 0.2009 0.7334 0.067 Uiso 1 1 calc R U . . .
C3 C 1.1944(11) 0.1120(5) 0.6824(4) 0.056(2) Uani 1 1 d . . . . .
H3A H 1.2393 0.1484 0.6456 0.067 Uiso 1 1 calc R U . . .
O3 O 0.5799(15) 0.1235(6) 0.8809(8) 0.064(5) Uani 0.5 1 d D U P A -1
O4 O 0.4755(13) 0.2609(8) 0.8791(9) 0.066(5) Uani 0.5 1 d D U P A -1
N4 N 0.8731(11) 0.1958(7) 0.8854(6) 0.050(3) Uani 0.5 1 d D U P B -1
N5 N 0.7664(13) 0.3386(5) 0.8859(6) 0.048(3) Uani 0.5 1 d D U P B -1
N6 N 0.5884(10) 0.2078(7) 0.8814(7) 0.048(3) Uani 0.5 1 d D U P A -1
C4 C 0.7500 0.2500 0.8830(5) 0.045(2) Uani 1 2 d DS TU P . .
C5 C 0.9926(14) 0.2613(10) 0.8842(10) 0.058(5) Uani 0.5 1 d D U P B -1
H5B H 1.1021 0.2483 0.8793 0.069 Uiso 0.5 1 calc R U P B -1
C6 C 0.9294(15) 0.3465(9) 0.8910(10) 0.046(4) Uani 0.5 1 d D U P B -1
H6A H 0.9867 0.4019 0.8981 0.055 Uiso 0.5 1 calc R U P B -1
O5 O 0.829(3) -0.0703(10) 1.0752(9) 0.056(6) Uani 0.5 1 d D . P B -1
O6 O 0.744(3) -0.0260(12) 0.9690(11) 0.063(7) Uani 0.5 1 d D . P B -1
N8 N 1.0315(15) 0.0425(8) 0.9396(6) 0.046(3) Uani 0.5 1 d D . P B -1
N9 N 0.8423(16) -0.0341(8) 1.0162(10) 0.045(3) Uani 0.5 1 d D . P B -1
N7 N 1.1197(14) -0.0019(8) 1.0460(6) 0.045(3) Uani 0.5 1 d D . P B -1
C7 C 1.0000 0.0000 1.0000 0.038(2) Uani 1 2 d DS . P . .
C8 C 1.243(3) 0.0394(12) 1.0113(13) 0.039(6) Uani 0.5 1 d D . P B -1
H8A H 1.3469 0.0476 1.0292 0.047 Uiso 0.5 1 calc R U P B -1
C9 C 1.189(2) 0.0665(14) 0.9463(13) 0.047(7) Uani 0.5 1 d D . P B -1
H9A H 1.2497 0.0971 0.9111 0.056 Uiso 0.5 1 calc R U P B -1


_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 N8 2.019(12) . ?
Zn1 N4 2.043(10) . ?
Zn1 N1 2.047(7) . ?
Zn1 N2 2.055(7) 3_456 ?
O1 N3 1.222(8) . ?
O2 N3 1.212(8) . ?
N1 C1 1.323(10) . ?
N1 C2 1.336(10) . ?
N2 C1 1.319(10) . ?
N2 C3 1.357(10) . ?
N2 Zn1 2.055(7) 3_556 ?
N3 C1 1.450(10) . ?
C2 C3 1.375(12) . ?
C2 H2B 0.9500 . ?
C3 H3A 0.9500 . ?
O3 N6 1.229(9) . ?
O4 N6 1.230(9) . ?
N4 C4 1.307(8) . ?
N4 C5 1.390(9) . ?
N5 C4 1.298(7) . ?
N5 C6 1.388(9) . ?
N6 C4 1.499(8) . ?
C5 C6 1.356(10) . ?
C5 H5B 0.9500 . ?
C6 H6A 0.9500 . ?
O5 N9 1.234(16) . ?
O6 N9 1.225(17) . ?
N8 C7 1.319(11) . ?
N8 C9 1.38(2) . ?
N9 C7 1.456(13) . ?
N7 C7 1.333(10) . ?
N7 C8 1.368(19) . ?
C8 C9 1.364(19) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?

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
N8 Zn1 N4 87.0(4) . . ?
N8 Zn1 N1 100.1(4) . . ?
N4 Zn1 N1 99.8(4) . . ?
N8 Zn1 N2 133.1(4) . 3_456 ?
N4 Zn1 N2 131.1(3) . 3_456 ?
N1 Zn1 N2 98.9(3) . 3_456 ?
C1 N1 C2 103.7(7) . . ?
C1 N1 Zn1 125.1(5) . . ?
C2 N1 Zn1 130.9(6) . . ?
C1 N2 C3 103.2(7) . . ?
C1 N2 Zn1 128.3(5) . 3_556 ?
C3 N2 Zn1 128.3(6) . 3_556 ?
O2 N3 O1 124.4(7) . . ?
O2 N3 C1 118.1(7) . . ?
O1 N3 C1 117.5(7) . . ?
N2 C1 N1 115.7(7) . . ?
N2 C1 N3 122.2(7) . . ?
N1 C1 N3 122.0(7) . . ?
N1 C2 C3 109.0(7) . . ?
N1 C2 H2B 125.5 . . ?
C3 C2 H2B 125.5 . . ?
N2 C3 C2 108.3(7) . . ?
N2 C3 H3A 125.8 . . ?
C2 C3 H3A 125.8 . . ?
C4 N4 C5 99.6(7) . . ?
C4 N4 Zn1 128.0(7) . . ?
C5 N4 Zn1 127.5(8) . . ?
C4 N5 C6 101.0(7) . . ?
O3 N6 O4 125.5(10) . . ?
O3 N6 C4 117.6(9) . . ?
O4 N6 C4 116.9(9) . . ?
N5 C4 N4 120.8(6) . . ?
N5 C4 N6 120.3(6) . . ?
N4 C4 N6 118.7(6) . . ?
C6 C5 N4 109.7(9) . . ?
C6 C5 H5B 125.1 . . ?
N4 C5 H5B 125.1 . . ?
C5 C6 N5 108.1(9) . . ?
C5 C6 H6A 126.0 . . ?
N5 C6 H6A 126.0 . . ?
C7 N8 C9 103.6(14) . . ?
C7 N8 Zn1 128.1(8) . . ?
C9 N8 Zn1 128.2(14) . . ?
O6 N9 O5 129.0(19) . . ?
O6 N9 C7 116.1(17) . . ?
O5 N9 C7 114.8(17) . . ?
C7 N7 C8 105.1(14) . . ?
N8 C7 N7 114.5(8) . . ?
N8 C7 N9 121.7(9) . . ?
N7 C7 N9 123.6(9) . . ?
C9 C8 N7 107(2) . . ?
C9 C8 H8A 126.3 . . ?
N7 C8 H8A 126.3 . . ?
C8 C9 N8 109(2) . . ?
C8 C9 H9A 125.3 . . ?
N8 C9 H9A 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 N1 2.3(10) . . . . ?
Zn1 N2 C1 N1 177.4(6) 3_556 . . . ?
C3 N2 C1 N3 179.0(8) . . . . ?
Zn1 N2 C1 N3 -5.8(12) 3_556 . . . ?
C2 N1 C1 N2 -1.4(10) . . . . ?
Zn1 N1 C1 N2 172.8(6) . . . . ?
C2 N1 C1 N3 -178.2(8) . . . . ?
Zn1 N1 C1 N3 -4.0(12) . . . . ?
O2 N3 C1 N2 2.8(13) . . . . ?
O1 N3 C1 N2 -178.1(8) . . . . ?
O2 N3 C1 N1 179.4(8) . . . . ?
O1 N3 C1 N1 -1.5(12) . . . . ?
C1 N1 C2 C3 -0.1(10) . . . . ?
Zn1 N1 C2 C3 -173.8(6) . . . . ?
C1 N2 C3 C2 -2.2(10) . . . . ?
Zn1 N2 C3 C2 -177.3(6) 3_556 . . . ?
N1 C2 C3 N2 1.5(11) . . . . ?
C6 N5 C4 N4 0.1(14) . . . . ?
C6 N5 C4 N6 176.3(10) . . . . ?
C5 N4 C4 N5 -5.3(12) . . . . ?
Zn1 N4 C4 N5 -161.6(10) . . . . ?
C5 N4 C4 N6 178.5(9) . . . . ?
Zn1 N4 C4 N6 22.2(14) . . . . ?
O3 N6 C4 N5 -177.8(11) . . . . ?
O4 N6 C4 N5 3.8(16) . . . . ?
O3 N6 C4 N4 -1.6(14) . . . . ?
O4 N6 C4 N4 -180.0(9) . . . . ?
C4 N4 C5 C6 8.3(12) . . . . ?
Zn1 N4 C5 C6 164.8(12) . . . . ?
N4 C5 C6 N5 -9.0(15) . . . . ?
C4 N5 C6 C5 5.4(14) . . . . ?
C9 N8 C7 N7 2.9(10) . . . . ?
Zn1 N8 C7 N7 179.7(7) . . . . ?
C9 N8 C7 N9 177.7(10) . . . . ?
Zn1 N8 C7 N9 -5.6(13) . . . . ?
C8 N7 C7 N8 -3.0(10) . . . . ?
C8 N7 C7 N9 -177.6(9) . . . . ?
O6 N9 C7 N8 4.3(13) . . . . ?
O5 N9 C7 N8 -178.2(9) . . . . ?
O6 N9 C7 N7 178.5(9) . . . . ?
O5 N9 C7 N7 -4.0(12) . . . . ?
C7 N7 C8 C9 1.8(13) . . . . ?
N7 C8 C9 N8 -0.1(16) . . . . ?
C7 N8 C9 C8 -1.7(14) . . . . ?
Zn1 N8 C9 C8 -178.4(9) . . . . ?

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.094

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
