# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1473389'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014


_chemical_name_systematic        
;
Poly[(mu-6-aminopyridine-3-carboxylato-kN:kO)zinc(II)] 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4 O4 Zn'
_chemical_formula_sum            'C12 H10 N4 O4 Zn'
_chemical_formula_weight         339.61

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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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+1/4'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'y+1/2, -x+1/2, z+1/4'
'-y+1/2, x+1/2, z+3/4'
'-y, -x, -z+1/2'

_cell_length_a                   7.8691(7)
_cell_length_b                   7.8691(7)
_cell_length_c                   22.353(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1384.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13404
_cell_measurement_theta_min      2.744
_cell_measurement_theta_max      28.753

_exptl_crystal_description       'trigonal antiprism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.795
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker Venture'
_diffrn_measurement_method       ω
_diffrn_reflns_number            13404
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.744
_diffrn_reflns_theta_max         28.753
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1796
_reflns_number_gt                1718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.600
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'Sir92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.9161P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_restrained_S_all      1.235
_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 0.61567(8) 0.38433(8) 0.7500 0.01295(19) Uani 1 2 d S T P . .
N1 N 0.5820(6) 0.5870(6) 0.69297(19) 0.0157(9) Uani 1 1 d . . . . .
C2 C 0.6025(8) 0.7397(7) 0.7193(2) 0.0153(10) Uani 1 1 d . . . . .
H2 H 0.6354 0.7414 0.7592 0.018 Uiso 1 1 calc R U . . .
C3 C 0.5784(6) 0.8926(8) 0.6913(2) 0.0138(10) Uani 1 1 d . . . . .
C4 C 0.5261(7) 0.8916(8) 0.6307(2) 0.0209(11) Uani 1 1 d . . . . .
H4 H 0.5063 0.9928 0.6103 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5053(9) 0.7371(8) 0.6026(3) 0.0257(13) Uani 1 1 d . . . . .
H5 H 0.4723 0.7335 0.5627 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5338(8) 0.5846(7) 0.6340(3) 0.0199(12) Uani 1 1 d . . . . .
C7 C 0.6039(8) 1.0534(7) 0.7249(2) 0.0154(10) Uani 1 1 d . . . . .
O1 O 0.5519(6) 1.1909(5) 0.69926(18) 0.0184(9) Uani 1 1 d . . . . .
O2 O 0.6722(6) 1.0538(5) 0.77467(18) 0.0237(10) Uani 1 1 d . . . . .
N8 N 0.5132(8) 0.4317(6) 0.6083(3) 0.0355(16) Uani 1 1 d . . . . .
H81 H 0.5301 0.3407 0.6287 0.043 Uiso 1 1 calc R U . . .
H82 H 0.4830 0.4249 0.5714 0.043 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 O1 1.963(4) 8_766 ?
Zn1 O1 1.963(4) 1_545 ?
Zn1 N1 2.059(4) 8_666 ?
Zn1 N1 2.059(4) . ?
N1 C2 1.347(6) . ?
N1 C6 1.372(7) . ?
C2 C3 1.370(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.415(7) . ?
C3 C7 1.485(7) . ?
C4 C5 1.378(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(8) . ?
C5 H5 0.9300 . ?
C6 N8 1.343(7) . ?
C7 O2 1.236(7) . ?
C7 O1 1.291(6) . ?
O1 Zn1 1.963(4) 1_565 ?
N8 H81 0.8600 . ?
N8 H82 0.8600 . ?

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 Zn1 O1 136.9(2) 8_766 1_545 ?
O1 Zn1 N1 102.12(15) 8_766 8_666 ?
O1 Zn1 N1 105.03(17) 1_545 8_666 ?
O1 Zn1 N1 105.03(17) 8_766 . ?
O1 Zn1 N1 102.11(15) 1_545 . ?
N1 Zn1 N1 100.6(3) 8_666 . ?
C2 N1 C6 117.7(5) . . ?
C2 N1 Zn1 113.9(3) . . ?
C6 N1 Zn1 128.3(4) . . ?
N1 C2 C3 124.6(5) . . ?
N1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 118.2(5) . . ?
C2 C3 C7 119.9(4) . . ?
C4 C3 C7 121.9(5) . . ?
C5 C4 C3 118.4(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N8 C6 N1 117.2(5) . . ?
N8 C6 C5 122.0(5) . . ?
N1 C6 C5 120.7(5) . . ?
O2 C7 O1 122.3(5) . . ?
O2 C7 C3 121.1(5) . . ?
O1 C7 C3 116.6(5) . . ?
C7 O1 Zn1 108.2(3) . 1_565 ?
C6 N8 H81 120.0 . . ?
C6 N8 H82 120.0 . . ?
H81 N8 H82 120.0 . . ?

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
N8 H81 O1 0.86 1.98 2.797(7) 159.0 1_545
N8 H82 O2 0.86 2.26 2.818(7) 122.1 7_644

_refine_diff_density_max         0.688
_refine_diff_density_min         -1.356
_refine_diff_density_rms         0.111

_shelxl_version_number           2014-3




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'Water, methanol'
_exptl_crystal_preparation       Luminescent
