# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_try5_BuOH
_database_code_depnum_ccdc_archive 'CCDC 1428296'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Zinc aminotriazolato oxalate'
_chemical_name_common            'Zinc aminotriazolato oxalate'
_chemical_melting_point          ?
_chemical_formula_moiety         Zn2(C2O4)(C2H3N4)2(H2O)
_chemical_formula_sum            'C6 H6 N8 O5 Zn2'
_chemical_formula_weight         400.93

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   17.576(4)
_cell_length_b                   7.9026(16)
_cell_length_c                   10.347(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.213(7)
_cell_angle_gamma                90
_cell_volume                     1414.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9459
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      68.54

_exptl_crystal_description       'hexagonal plates'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    4.533
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5981
_exptl_absorpt_correction_T_max  0.7364
_exptl_absorpt_process_details   'SADABS;Universitat Gottingen,1997'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         Micro-focus
_diffrn_radiation_monochromator  Micro-focus
_diffrn_measurement_device_type  'D8 Venture APEX-II'
_diffrn_measurement_method       'CMOS-Photon 100'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10881
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.554
_diffrn_reflns_theta_max         68.705
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             2517
_reflns_number_gt                2239
_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.

 In ZnAtzOx_BuOH case, it was extremely difficult to obtain x-ray 
 diffraction quality crystals with reasonable size. 
 Unfortunately sufficiently sized crystals were all twinned.
 This resulted in strong spurious diffraction spots adjacent
 to the metal. This was evident from the presence strong spurious
 peaks adjacent to the metals and some of the other framework 
 atoms even in the  'squeezed'file (PLATON, 40 M- version 290610,
 A.L.Spek, 1980-2010). 

 The solvent or extra-framework guest atoms were heavily 
 disordered and hence locating or fixing the solvent atoms proved
 difficult. A squeeze routine indicated the presence of 109 e-/cell
 which would correspond to 2.7molecules of BuOH in the unit cell. 
 However, this is much higher than what is observed from analytical
 results. This discrepancy can be due to the excess spurious e- 
 densities resulting from twinning creating interference during the 
 squeeze routine. 

 We tried different absorption correction models (spherical,
 numerical) considering the material to be weak to strong 
 absorber, yet there was no appreciable difference in the 
 refined data. This suggests that the problem is more to do
 with the twinning associated with the crystals. 

 We tried using 'reciprocal lattice' to isolate the different
 twin components and to carry out twin refinement routines, 
 but our efforts were not successful. We could see from the 
 reciprocal lattice images that the twinning was mostly not 
 of a simple merohedral kind.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1652P)²+37.3893P] 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         2517
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.1084
_refine_ls_wR_factor_ref         0.3127
_refine_ls_wR_factor_gt          0.3081
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.34300(8) 0.56006(17) -0.04539(14) 0.0230(5) Uani 1 1 d . . . . .
Zn2 Zn 0.15536(7) 0.44280(18) 0.08166(13) 0.0226(5) Uani 1 1 d . . . . .
N1 N 0.2581(5) 0.3842(13) -0.1183(10) 0.032(2) Uani 1 1 d . . . . .
N2 N 0.1895(5) 0.3487(12) -0.0801(8) 0.0259(19) Uani 1 1 d . . . . .
C3 C 0.1502(6) 0.2487(17) -0.1672(12) 0.035(3) Uani 1 1 d . . . . .
H3 H 0.1005 0.2051 -0.1612 0.042 Uiso 1 1 calc R U . . .
N3 N 0.1876(5) 0.2140(12) -0.2663(9) 0.029(2) Uani 1 1 d . . . . .
C4 C 0.2546(6) 0.3001(15) -0.2314(11) 0.030(2) Uani 1 1 d . . . . .
N4 N 0.3105(7) 0.3004(18) -0.3046(13) 0.059(4) Uani 1 1 d . . . . .
H4A H 0.3531 0.3588 -0.2790 0.071 Uiso 1 1 calc R U . . .
H4B H 0.3045 0.2421 -0.3782 0.071 Uiso 1 1 calc R U . . .
N5 N 0.3125(5) 0.6315(12) 0.1220(9) 0.0258(19) Uani 1 1 d . . . . .
N6 N 0.2388(5) 0.6280(12) 0.1491(9) 0.028(2) Uani 1 1 d . . . . .
C5 C 0.3521(6) 0.7160(15) 0.2206(12) 0.031(2) Uani 1 1 d . . . . .
H5 H 0.4061 0.7363 0.2294 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2405(7) 0.7122(17) 0.2584(14) 0.039(3) Uani 1 1 d . . . . .
N7 N 0.3102(5) 0.7709(12) 0.3072(9) 0.028(2) Uani 1 1 d . . . . .
N8 N 0.1782(7) 0.730(2) 0.3197(14) 0.069(5) Uani 1 1 d . . . . .
H8A H 0.1338 0.6826 0.2858 0.082 Uiso 1 1 calc R U . . .
H8B H 0.1826 0.7877 0.3932 0.082 Uiso 1 1 calc R U . . .
C1 C 0.0097(7) 0.5947(16) 0.0008(14) 0.037(3) Uani 1 1 d . . . . .
O1 O 0.0778(5) 0.6370(12) 0.0415(12) 0.051(3) Uani 1 1 d . . . . .
O2 O -0.0454(4) 0.6908(11) -0.0413(10) 0.042(2) Uani 1 1 d . . . . .
C2 C 0.4907(7) 0.4079(15) -0.0111(12) 0.031(2) Uani 1 1 d . . . . .
O3 O 0.4207(4) 0.3677(11) -0.0373(10) 0.040(2) Uani 1 1 d . . . . .
O4 O 0.5470(4) 0.3050(10) -0.0030(10) 0.038(2) Uani 1 1 d . . . . .
O100 O 0.0222(19) 0.522(3) 0.675(3) 0.089(10) Uani 0.5 1 d . . P . .
O101 O 0.5413(11) 0.527(2) 0.347(2) 0.049(5) Uani 0.5 1 d . . P . .


_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 N5 1.984(9) . ?
Zn1 N7 2.033(9) 4_575 ?
Zn1 O3 2.035(8) . ?
Zn1 N1 2.081(10) . ?
Zn1 O4 2.187(8) 3_665 ?
Zn2 N3 2.003(9) 4_566 ?
Zn2 N2 2.018(8) . ?
Zn2 O1 2.046(9) . ?
Zn2 N6 2.102(9) . ?
Zn2 O2 2.177(8) 3_565 ?
N1 C4 1.338(15) . ?
N1 N2 1.361(13) . ?
N2 C3 1.302(15) . ?
C3 N3 1.342(15) . ?
N3 C4 1.353(15) . ?
N3 Zn2 2.003(9) 4_565 ?
C4 N4 1.343(16) . ?
N5 C5 1.312(15) . ?
N5 N6 1.373(12) . ?
N6 C6 1.307(16) . ?
C5 N7 1.329(14) . ?
C6 N7 1.324(15) . ?
C6 N8 1.365(16) . ?
N7 Zn1 2.033(9) 4_576 ?
C1 O1 1.241(15) . ?
C1 O2 1.248(15) . ?
C1 C1 1.53(3) 3_565 ?
O2 Zn2 2.177(8) 3_565 ?
C2 O3 1.253(15) . ?
C2 O4 1.272(14) . ?
C2 C2 1.50(2) 3_665 ?
O4 Zn1 2.187(8) 3_665 ?

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
N5 Zn1 N7 112.5(4) . 4_575 ?
N5 Zn1 O3 117.4(4) . . ?
N7 Zn1 O3 128.4(4) 4_575 . ?
N5 Zn1 N1 102.6(4) . . ?
N7 Zn1 N1 94.4(4) 4_575 . ?
O3 Zn1 N1 87.1(4) . . ?
N5 Zn1 O4 91.5(4) . 3_665 ?
N7 Zn1 O4 88.4(4) 4_575 3_665 ?
O3 Zn1 O4 78.2(3) . 3_665 ?
N1 Zn1 O4 163.2(4) . 3_665 ?
N3 Zn2 N2 109.8(4) 4_566 . ?
N3 Zn2 O1 135.1(5) 4_566 . ?
N2 Zn2 O1 113.2(4) . . ?
N3 Zn2 N6 94.9(4) 4_566 . ?
N2 Zn2 N6 103.8(4) . . ?
O1 Zn2 N6 86.9(4) . . ?
N3 Zn2 O2 88.2(4) 4_566 3_565 ?
N2 Zn2 O2 92.7(4) . 3_565 ?
O1 Zn2 O2 77.7(3) . 3_565 ?
N6 Zn2 O2 160.9(4) . 3_565 ?
C4 N1 N2 104.3(9) . . ?
C4 N1 Zn1 124.6(8) . . ?
N2 N1 Zn1 130.3(7) . . ?
C3 N2 N1 108.3(9) . . ?
C3 N2 Zn2 126.7(8) . . ?
N1 N2 Zn2 125.0(7) . . ?
N2 C3 N3 112.4(10) . . ?
C3 N3 C4 102.4(9) . . ?
C3 N3 Zn2 128.1(8) . 4_565 ?
C4 N3 Zn2 129.3(8) . 4_565 ?
N1 C4 N4 124.7(11) . . ?
N1 C4 N3 112.7(10) . . ?
N4 C4 N3 122.6(11) . . ?
C5 N5 N6 103.9(9) . . ?
C5 N5 Zn1 129.5(7) . . ?
N6 N5 Zn1 125.7(7) . . ?
C6 N6 N5 106.9(9) . . ?
C6 N6 Zn2 123.3(8) . . ?
N5 N6 Zn2 125.0(7) . . ?
N5 C5 N7 114.2(9) . . ?
N6 C6 N7 112.6(10) . . ?
N6 C6 N8 123.8(11) . . ?
N7 C6 N8 123.4(12) . . ?
C6 N7 C5 102.4(9) . . ?
C6 N7 Zn1 129.5(8) . 4_576 ?
C5 N7 Zn1 127.1(7) . 4_576 ?
O1 C1 O2 126.7(12) . . ?
O1 C1 C1 117.8(14) . 3_565 ?
O2 C1 C1 115.6(13) . 3_565 ?
C1 O1 Zn2 115.8(9) . . ?
C1 O2 Zn2 112.3(8) . 3_565 ?
O3 C2 O4 125.1(11) . . ?
O3 C2 C2 117.2(13) . 3_665 ?
O4 C2 C2 117.7(13) . 3_665 ?
C2 O3 Zn1 116.5(8) . . ?
C2 O4 Zn1 110.4(8) . 3_665 ?

_refine_diff_density_max         2.146
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.270

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_trial1_a_PrOH
_database_code_depnum_ccdc_archive 'CCDC 1428298'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Zinc aminotriazolato oxalate'
_chemical_name_common            'Zinc aminotriazolato oxalate'
_chemical_melting_point          ?
_chemical_formula_moiety         Zn2(C2O4)(C2H3N4)2(C3H8O)
_chemical_formula_sum            'C9 H14 N8 O5 Zn2'
_chemical_formula_weight         445.02

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                   9.1877(4)
_cell_length_b                   13.6108(6)
_cell_length_c                   12.5305(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.6290(10)
_cell_angle_gamma                90
_cell_volume                     1516.16(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      4.88
_cell_measurement_theta_max      72.14

_exptl_crystal_description       'hexagonal plates'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.301
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS;Universitat Gottingen,1997'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         Micro-focus
_diffrn_radiation_monochromator  Micro-focus
_diffrn_measurement_device_type  'D8 Venture APEX-II'
_diffrn_measurement_method       'CMOS-Photon 100'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18940
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.885
_diffrn_reflns_theta_max         72.129
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2975
_reflns_number_gt                2878
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0344P)²+2.7576P] 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         2975
_refine_ls_number_parameters     216
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.008
_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
Zn01 Zn 0.53762(3) 0.47874(2) 0.35723(2) 0.01405(9) Uani 1 1 d . . . . .
Zn02 Zn -0.10126(3) 0.41132(2) 0.06863(2) 0.01412(9) Uani 1 1 d . . . . .
C1 C 0.7185(3) 0.51233(17) 0.19257(19) 0.0180(5) Uani 1 1 d . . . . .
O1 O 0.6370(2) 0.56559(13) 0.23273(15) 0.0260(4) Uani 1 1 d . . . . .
O2 O 0.7748(2) 0.53115(13) 0.11310(15) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.7559(3) 0.41076(17) 0.2462(2) 0.0188(5) Uani 1 1 d . . . . .
O3 O 0.6957(2) 0.38870(13) 0.32255(14) 0.0232(4) Uani 1 1 d . . . . .
O4 O 0.8443(2) 0.35727(13) 0.21147(15) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.3085(3) 0.55019(19) 0.1560(2) 0.0224(5) Uani 1 1 d . . . . .
H3 H 0.3781 0.5984 0.1450 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2088(3) 0.43450(19) 0.2246(2) 0.0227(5) Uani 1 1 d . . . . .
N1 N 0.3372(2) 0.48699(15) 0.24231(17) 0.0201(4) Uani 1 1 d . . . . .
N2 N 0.1087(2) 0.46149(15) 0.13307(16) 0.0184(4) Uani 1 1 d . . . . .
N3 N 0.1751(2) 0.53793(14) 0.08940(16) 0.0179(4) Uani 1 1 d . . . . .
N4 N 0.1821(3) 0.3619(2) 0.2925(2) 0.0469(8) Uani 1 1 d . . . . .
H4A H 0.0954 0.3306 0.2763 0.056 Uiso 1 1 calc R U . . .
H4B H 0.2516 0.3463 0.3524 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6034(3) 0.68813(17) 0.41029(19) 0.0202(5) Uani 1 1 d . . . . .
H5 H 0.6497 0.6941 0.3508 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5038(3) 0.72376(17) 0.53989(19) 0.0174(4) Uani 1 1 d . . . . .
N5 N 0.5670(2) 0.60363(14) 0.44645(16) 0.0167(4) Uani 1 1 d . . . . .
N6 N 0.5011(2) 0.62564(14) 0.53268(15) 0.0153(4) Uani 1 1 d . . . . .
N7 N 0.5686(2) 0.76565(14) 0.46561(16) 0.0179(4) Uani 1 1 d . . . . .
N8 N 0.4511(3) 0.77495(17) 0.6148(2) 0.0340(6) Uani 1 1 d . . . . .
H8A H 0.4122 0.7437 0.6625 0.041 Uiso 1 1 calc R U . . .
H8B H 0.4557 0.8395 0.6158 0.041 Uiso 1 1 calc R U . . .
O1SA O 0.9893(9) 0.1218(5) 0.5442(7) 0.0535(19) Uiso 0.452(11) 1 d D U P A 1
H1SA H 1.0809 0.1159 0.5764 0.080 Uiso 0.452(11) 1 calc R U P A 1
C1SA C 0.9333(14) 0.2117(8) 0.5774(11) 0.081(4) Uiso 0.452(11) 1 d D U P A 1
H1S1 H 0.9417 0.2062 0.6575 0.098 Uiso 0.452(11) 1 calc R U P A 1
H1S2 H 0.8245 0.2142 0.5405 0.098 Uiso 0.452(11) 1 calc R U P A 1
C2SA C 0.9966(17) 0.3083(10) 0.5595(13) 0.103(5) Uiso 0.452(11) 1 d D U P A 1
H2S1 H 0.9820 0.3221 0.4799 0.123 Uiso 0.452(11) 1 calc R U P A 1
H2S2 H 1.1051 0.3122 0.5968 0.123 Uiso 0.452(11) 1 calc R U P A 1
C3SA C 0.9038(14) 0.3794(9) 0.6122(10) 0.069(3) Uiso 0.452(11) 1 d D U P A 1
H3S1 H 0.8342 0.3418 0.6440 0.103 Uiso 0.452(11) 1 calc R U P A 1
H3S2 H 0.8466 0.4242 0.5556 0.103 Uiso 0.452(11) 1 calc R U P A 1
H3S3 H 0.9718 0.4176 0.6703 0.103 Uiso 0.452(11) 1 calc R U P A 1
O1SB O 1.0210(9) 0.1318(6) 0.5233(7) 0.073(2) Uiso 0.548(11) 1 d D U P A 2
H1SB H 0.9414 0.1007 0.5213 0.110 Uiso 0.548(11) 1 calc R U P A 2
C1SB C 0.9903(10) 0.2294(6) 0.5118(7) 0.065(3) Uiso 0.548(11) 1 d D U P A 2
H1S3 H 0.9200 0.2404 0.4386 0.078 Uiso 0.548(11) 1 calc R U P A 2
H1S4 H 1.0848 0.2647 0.5124 0.078 Uiso 0.548(11) 1 calc R U P A 2
C2SB C 0.9222(18) 0.2751(11) 0.5995(12) 0.127(5) Uiso 0.548(11) 1 d D U P A 2
H2S3 H 0.9749 0.2520 0.6742 0.153 Uiso 0.548(11) 1 calc R U P A 2
H2S4 H 0.8139 0.2591 0.5856 0.153 Uiso 0.548(11) 1 calc R U P A 2
C3SB C 0.9483(15) 0.3956(9) 0.5855(11) 0.092(4) Uiso 0.548(11) 1 d D U P A 2
H3S4 H 1.0193 0.4057 0.5399 0.139 Uiso 0.548(11) 1 calc R U P A 2
H3S5 H 0.9888 0.4250 0.6583 0.139 Uiso 0.548(11) 1 calc R U P A 2
H3S6 H 0.8520 0.4266 0.5501 0.139 Uiso 0.548(11) 1 calc R U P A 2


_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
Zn01 N5 2.015(2) . ?
Zn01 O3 2.0298(17) . ?
Zn01 N1 2.034(2) . ?
Zn01 N6 2.0725(19) 3_666 ?
Zn01 O1 2.3203(18) . ?
Zn02 N2 2.013(2) . ?
Zn02 N3 2.044(2) 3_565 ?
Zn02 N7 2.066(2) 2_545 ?
Zn02 O4 2.1086(17) 1_455 ?
Zn02 O2 2.1419(17) 1_455 ?
C1 O1 1.237(3) . ?
C1 O2 1.259(3) . ?
C1 C2 1.538(3) . ?
O2 Zn02 2.1420(17) 1_655 ?
C2 O4 1.249(3) . ?
C2 O3 1.256(3) . ?
O4 Zn02 2.1086(17) 1_655 ?
C3 N3 1.307(3) . ?
C3 N1 1.355(3) . ?
C3 H3 0.9500 . ?
C4 N2 1.328(3) . ?
C4 N1 1.349(3) . ?
C4 N4 1.366(4) . ?
N2 N3 1.387(3) . ?
N3 Zn02 2.044(2) 3_565 ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C5 N5 1.310(3) . ?
C5 N7 1.344(3) . ?
C5 H5 0.9500 . ?
C6 N6 1.338(3) . ?
C6 N7 1.351(3) . ?
C6 N8 1.353(3) . ?
N5 N6 1.398(3) . ?
N6 Zn01 2.0725(19) 3_666 ?
N7 Zn02 2.066(2) 2 ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
O1SA C1SA 1.429(12) . ?
O1SA H1SA 0.8400 . ?
C1SA C2SA 1.478(15) . ?
C1SA H1S1 0.9900 . ?
C1SA H1S2 0.9900 . ?
C2SA C3SA 1.543(14) . ?
C2SA H2S1 0.9900 . ?
C2SA H2S2 0.9900 . ?
C3SA H3S1 0.9800 . ?
C3SA H3S2 0.9800 . ?
C3SA H3S3 0.9800 . ?
O1SB C1SB 1.358(10) . ?
O1SB H1SB 0.8400 . ?
C1SB C2SB 1.527(14) . ?
C1SB H1S3 0.9900 . ?
C1SB H1S4 0.9900 . ?
C2SB C3SB 1.673(14) . ?
C2SB H2S3 0.9900 . ?
C2SB H2S4 0.9900 . ?
C3SB H3S4 0.9800 . ?
C3SB H3S5 0.9800 . ?
C3SB H3S6 0.9800 . ?

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
N5 Zn01 O3 128.70(8) . . ?
N5 Zn01 N1 108.47(8) . . ?
O3 Zn01 N1 116.79(8) . . ?
N5 Zn01 N6 103.33(7) . 3_666 ?
O3 Zn01 N6 88.91(7) . 3_666 ?
N1 Zn01 N6 103.42(8) . 3_666 ?
N5 Zn01 O1 85.58(7) . . ?
O3 Zn01 O1 74.89(7) . . ?
N1 Zn01 O1 86.30(8) . . ?
N6 Zn01 O1 163.64(7) 3_666 . ?
N2 Zn02 N3 108.91(8) . 3_565 ?
N2 Zn02 N7 103.54(8) . 2_545 ?
N3 Zn02 N7 98.81(8) 3_565 2_545 ?
N2 Zn02 O4 100.74(8) . 1_455 ?
N3 Zn02 O4 148.00(8) 3_565 1_455 ?
N7 Zn02 O4 85.38(7) 2_545 1_455 ?
N2 Zn02 O2 98.97(8) . 1_455 ?
N3 Zn02 O2 85.78(7) 3_565 1_455 ?
N7 Zn02 O2 154.05(7) 2_545 1_455 ?
O4 Zn02 O2 77.83(6) 1_455 1_455 ?
O1 C1 O2 127.9(2) . . ?
O1 C1 C2 116.1(2) . . ?
O2 C1 C2 115.9(2) . . ?
C1 O1 Zn01 110.88(15) . . ?
C1 O2 Zn02 113.74(15) . 1_655 ?
O4 C2 O3 125.2(2) . . ?
O4 C2 C1 117.7(2) . . ?
O3 C2 C1 117.1(2) . . ?
C2 O3 Zn01 119.67(16) . . ?
C2 O4 Zn02 114.02(16) . 1_655 ?
N3 C3 N1 113.0(2) . . ?
N3 C3 H3 123.5 . . ?
N1 C3 H3 123.5 . . ?
N2 C4 N1 112.4(2) . . ?
N2 C4 N4 123.0(2) . . ?
N1 C4 N4 124.6(2) . . ?
C4 N1 C3 102.7(2) . . ?
C4 N1 Zn01 133.24(17) . . ?
C3 N1 Zn01 123.97(17) . . ?
C4 N2 N3 105.73(19) . . ?
C4 N2 Zn02 129.54(17) . . ?
N3 N2 Zn02 124.67(15) . . ?
C3 N3 N2 106.18(19) . . ?
C3 N3 Zn02 127.13(16) . 3_565 ?
N2 N3 Zn02 124.34(15) . 3_565 ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N5 C5 N7 113.3(2) . . ?
N5 C5 H5 123.3 . . ?
N7 C5 H5 123.3 . . ?
N6 C6 N7 112.2(2) . . ?
N6 C6 N8 123.8(2) . . ?
N7 C6 N8 123.9(2) . . ?
C5 N5 N6 106.09(18) . . ?
C5 N5 Zn01 123.98(16) . . ?
N6 N5 Zn01 125.88(14) . . ?
C6 N6 N5 105.17(18) . . ?
C6 N6 Zn01 129.98(16) . 3_666 ?
N5 N6 Zn01 123.23(14) . 3_666 ?
C5 N7 C6 103.14(19) . . ?
C5 N7 Zn02 125.46(15) . 2 ?
C6 N7 Zn02 131.31(16) . 2 ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C1SA O1SA H1SA 109.5 . . ?
O1SA C1SA C2SA 122.2(11) . . ?
O1SA C1SA H1S1 106.8 . . ?
C2SA C1SA H1S1 106.8 . . ?
O1SA C1SA H1S2 106.8 . . ?
C2SA C1SA H1S2 106.8 . . ?
H1S1 C1SA H1S2 106.6 . . ?
C1SA C2SA C3SA 102.3(11) . . ?
C1SA C2SA H2S1 111.3 . . ?
C3SA C2SA H2S1 111.3 . . ?
C1SA C2SA H2S2 111.3 . . ?
C3SA C2SA H2S2 111.3 . . ?
H2S1 C2SA H2S2 109.2 . . ?
C2SA C3SA H3S1 109.5 . . ?
C2SA C3SA H3S2 109.5 . . ?
H3S1 C3SA H3S2 109.5 . . ?
C2SA C3SA H3S3 109.5 . . ?
H3S1 C3SA H3S3 109.5 . . ?
H3S2 C3SA H3S3 109.5 . . ?
C1SB O1SB H1SB 109.5 . . ?
O1SB C1SB C2SB 115.7(9) . . ?
O1SB C1SB H1S3 108.4 . . ?
C2SB C1SB H1S3 108.4 . . ?
O1SB C1SB H1S4 108.4 . . ?
C2SB C1SB H1S4 108.4 . . ?
H1S3 C1SB H1S4 107.4 . . ?
C1SB C2SB C3SB 103.2(10) . . ?
C1SB C2SB H2S3 111.1 . . ?
C3SB C2SB H2S3 111.1 . . ?
C1SB C2SB H2S4 111.1 . . ?
C3SB C2SB H2S4 111.1 . . ?
H2S3 C2SB H2S4 109.1 . . ?
C2SB C3SB H3S4 109.5 . . ?
C2SB C3SB H3S5 109.5 . . ?
H3S4 C3SB H3S5 109.5 . . ?
C2SB C3SB H3S6 109.5 . . ?
H3S4 C3SB H3S6 109.5 . . ?
H3S5 C3SB H3S6 109.5 . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.078

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_try5_BuOH_squeezed
_database_code_depnum_ccdc_archive 'CCDC 1428299'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Zinc aminotriazolato oxalate'
_chemical_name_common            'Zinc aminotriazolato oxalate'
_chemical_melting_point          ?
_chemical_formula_moiety         Zn2(C2O4)(C2H3N4)2
_chemical_formula_sum            'C6 H6 N8 O4 Zn2'
_chemical_formula_weight         384.93

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   17.576(4)
_cell_length_b                   7.9026(16)
_cell_length_c                   10.347(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.213(7)
_cell_angle_gamma                90
_cell_volume                     1414.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9459
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      68.54

_exptl_crystal_description       'hexagonal plates'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    4.447
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5981
_exptl_absorpt_correction_T_max  0.7364
_exptl_absorpt_process_details   'SADABS;Universitat Gottingen,1997'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         Micro-focus
_diffrn_radiation_monochromator  Micro-focus
_diffrn_measurement_device_type  'D8 Venture APEX-II'
_diffrn_measurement_method       'CMOS-Photon 100'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10881
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.554
_diffrn_reflns_theta_max         68.705
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             2517
_reflns_number_gt                2207
_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.

 Severe twinning on the crystals resulted in strong spurious 
 diffraction spots adjacent to the metal atoms even in the '
 squeezed'file (PLATON, 40 M- version 290610, A.L.Spek, 1980-2010). 

 The solvent or extra-framework guest atoms were heavily 
 disordered and hence locating or fixing the solvent atoms proved
 difficult. A squeeze routine indicated the presence of 109 e-/cell
 which would correspond to 2.7molecules of BuOH in the unit cell. 
 However, this is much higher than what is observed from analytical
 results. This discrepancy can be due to the excess spurious e- 
 densities resulting from twinning creating interference during the 
 squeeze routine. 

. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1177P)²+28.3070P] 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         2517
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.2563
_refine_ls_wR_factor_gt          0.2530
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.34298(7) 0.56019(15) -0.04537(12) 0.0235(4) Uani 1 1 d . . . . .
Zn2 Zn 0.15538(6) 0.44284(15) 0.08173(11) 0.0232(4) Uani 1 1 d . . . . .
N1 N 0.2579(5) 0.3841(11) -0.1191(9) 0.0328(18) Uani 1 1 d . . . . .
N2 N 0.1892(4) 0.3493(10) -0.0805(7) 0.0259(16) Uani 1 1 d . . . . .
C3 C 0.1499(6) 0.2484(14) -0.1674(10) 0.034(2) Uani 1 1 d . . . . .
H3 H 0.1004 0.2041 -0.1614 0.041 Uiso 1 1 calc R U . . .
N3 N 0.1881(4) 0.2144(11) -0.2670(8) 0.0298(17) Uani 1 1 d . . . . .
C4 C 0.2542(6) 0.2995(13) -0.2320(9) 0.031(2) Uani 1 1 d . . . . .
N4 N 0.3105(6) 0.2996(15) -0.3047(11) 0.057(3) Uani 1 1 d . . . . .
H4A H 0.3046 0.2420 -0.3786 0.068 Uiso 1 1 calc R U . . .
H4B H 0.3533 0.3573 -0.2783 0.068 Uiso 1 1 calc R U . . .
N5 N 0.3126(4) 0.6317(10) 0.1219(7) 0.0262(16) Uani 1 1 d . . . . .
N6 N 0.2386(4) 0.6290(10) 0.1500(8) 0.0277(17) Uani 1 1 d . . . . .
C5 C 0.3522(5) 0.7155(13) 0.2203(10) 0.031(2) Uani 1 1 d . . . . .
H5 H 0.4062 0.7352 0.2293 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2401(6) 0.7120(15) 0.2574(12) 0.040(3) Uani 1 1 d . . . . .
N7 N 0.3102(4) 0.7707(11) 0.3066(7) 0.0285(17) Uani 1 1 d . . . . .
N8 N 0.1776(6) 0.7296(17) 0.3199(12) 0.068(4) Uani 1 1 d . . . . .
H8A H 0.1331 0.6825 0.2865 0.082 Uiso 1 1 calc R U . . .
H8B H 0.1821 0.7881 0.3933 0.082 Uiso 1 1 calc R U . . .
C1 C 0.0099(6) 0.5946(14) 0.0010(12) 0.039(2) Uani 1 1 d . . . . .
O1 O 0.0776(4) 0.6369(10) 0.0411(10) 0.051(2) Uani 1 1 d . . . . .
O2 O -0.0452(4) 0.6903(10) -0.0403(8) 0.0436(19) Uani 1 1 d . . . . .
C2 C 0.4910(6) 0.4085(13) -0.0109(10) 0.031(2) Uani 1 1 d . . . . .
O3 O 0.4205(4) 0.3673(9) -0.0376(9) 0.0415(19) Uani 1 1 d . . . . .
O4 O 0.5472(4) 0.3043(9) -0.0016(8) 0.0379(17) Uani 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 N5 1.982(7) . ?
Zn1 O3 2.037(7) . ?
Zn1 N7 2.038(8) 4_575 ?
Zn1 N1 2.085(8) . ?
Zn1 O4 2.186(7) 3_665 ?
Zn2 N3 2.001(8) 4_566 ?
Zn2 N2 2.018(7) . ?
Zn2 O1 2.048(8) . ?
Zn2 N6 2.107(8) . ?
Zn2 O2 2.179(7) 3_565 ?
N1 C4 1.338(13) . ?
N1 N2 1.365(11) . ?
N2 C3 1.305(13) . ?
C3 N3 1.353(12) . ?
N3 C4 1.335(13) . ?
N3 Zn2 2.001(8) 4_565 ?
C4 N4 1.345(14) . ?
N5 C5 1.307(12) . ?
N5 N6 1.381(10) . ?
N6 C6 1.287(13) . ?
C5 N7 1.329(12) . ?
C6 N7 1.330(13) . ?
C6 N8 1.377(13) . ?
N7 Zn1 2.038(8) 4_576 ?
C1 O1 1.234(13) . ?
C1 O2 1.243(13) . ?
C1 C1 1.53(2) 3_565 ?
O2 Zn2 2.179(7) 3_565 ?
C2 O3 1.262(13) . ?
C2 O4 1.276(12) . ?
C2 C2 1.49(2) 3_665 ?
O4 Zn1 2.186(7) 3_665 ?

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
N5 Zn1 O3 117.4(3) . . ?
N5 Zn1 N7 112.7(3) . 4_575 ?
O3 Zn1 N7 128.2(3) . 4_575 ?
N5 Zn1 N1 102.9(3) . . ?
O3 Zn1 N1 86.9(3) . . ?
N7 Zn1 N1 94.2(3) 4_575 . ?
N5 Zn1 O4 91.7(3) . 3_665 ?
O3 Zn1 O4 78.4(3) . 3_665 ?
N7 Zn1 O4 88.1(3) 4_575 3_665 ?
N1 Zn1 O4 162.9(3) . 3_665 ?
N3 Zn2 N2 109.7(3) 4_566 . ?
N3 Zn2 O1 135.6(4) 4_566 . ?
N2 Zn2 O1 112.8(4) . . ?
N3 Zn2 N6 94.9(3) 4_566 . ?
N2 Zn2 N6 104.2(3) . . ?
O1 Zn2 N6 86.8(3) . . ?
N3 Zn2 O2 88.6(3) 4_566 3_565 ?
N2 Zn2 O2 92.4(3) . 3_565 ?
O1 Zn2 O2 77.5(3) . 3_565 ?
N6 Zn2 O2 160.7(3) . 3_565 ?
C4 N1 N2 104.2(8) . . ?
C4 N1 Zn1 125.1(7) . . ?
N2 N1 Zn1 129.9(6) . . ?
C3 N2 N1 108.1(7) . . ?
C3 N2 Zn2 126.8(6) . . ?
N1 N2 Zn2 125.2(6) . . ?
N2 C3 N3 111.9(8) . . ?
C4 N3 C3 102.6(8) . . ?
C4 N3 Zn2 129.8(7) . 4_565 ?
C3 N3 Zn2 127.3(7) . 4_565 ?
N3 C4 N1 113.3(8) . . ?
N3 C4 N4 122.6(9) . . ?
N1 C4 N4 124.1(9) . . ?
C5 N5 N6 103.6(7) . . ?
C5 N5 Zn1 129.5(6) . . ?
N6 N5 Zn1 126.1(6) . . ?
C6 N6 N5 107.4(8) . . ?
C6 N6 Zn2 123.4(7) . . ?
N5 N6 Zn2 124.3(6) . . ?
N5 C5 N7 114.0(8) . . ?
N6 C6 N7 112.5(9) . . ?
N6 C6 N8 124.2(9) . . ?
N7 C6 N8 123.2(10) . . ?
C5 N7 C6 102.5(8) . . ?
C5 N7 Zn1 127.1(6) . 4_576 ?
C6 N7 Zn1 129.5(7) . 4_576 ?
O1 C1 O2 126.6(11) . . ?
O1 C1 C1 118.1(12) . 3_565 ?
O2 C1 C1 115.3(11) . 3_565 ?
C1 O1 Zn2 115.8(7) . . ?
C1 O2 Zn2 112.6(7) . 3_565 ?
O3 C2 O4 124.5(10) . . ?
O3 C2 C2 117.2(11) . 3_665 ?
O4 C2 C2 118.3(11) . 3_665 ?
C2 O3 Zn1 116.1(7) . . ?
C2 O4 Zn1 110.0(6) . 3_665 ?

_refine_diff_density_max         1.955
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.220
# SQUEEZE RESULTS (APPEND TO CIF)
# 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 0.500 0.000 0.000 87 27 ' '
2 0.000 0.000 0.000 86 27 ' '
3 0.500 0.500 0.500 87 27 ' '
4 1.000 0.500 0.500 86 27 ' '
_platon_squeeze_details          
;
;
_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_trial1_a_EtOH
_database_code_depnum_ccdc_archive 'CCDC 1438585'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Zinc aminotriazolato oxalate'
_chemical_name_common            'Zinc aminotriazolato oxalate'
_chemical_melting_point          ?
_chemical_formula_moiety         Zn2(C2O4)(C2H3N4)2(C2H6O)
_chemical_formula_sum            'C8 H11 N8 O5 Zn2'
_chemical_formula_weight         429.99

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                   8.9818(10)
_cell_length_b                   13.8656(13)
_cell_length_c                   12.4104(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.360(5)
_cell_angle_gamma                90
_cell_volume                     1490.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      73.21

_exptl_crystal_description       'hexagonal plates'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.351
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5594
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   'SADABS;Universitat Gottingen,1997'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         Micro-focus
_diffrn_radiation_monochromator  Micro-focus
_diffrn_measurement_device_type  'D8 Venture APEX-II'
_diffrn_measurement_method       'CMOS-Photon 100'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19147
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.881
_diffrn_reflns_theta_max         74.394
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2952
_reflns_number_gt                2648
_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.
 
  The structure has been solved in P21/n. 
 Unfortunately, the crystals were considerably twinned.
 This resulted in spurious diffraction spots adjacent
 to the metal.  
 The solvent ethanol molecule is disordered and has been modeled
 over two sites and with floating occupancy. 

 A squeeze routine (PLATON, 40 M- version 290610, A.L.Spek, 1980-2010)
 showed slight improvement in the R-values. Please see the cifcheck 
 response or the cif file of the squeezed version for comments on 
 squeeze results. 
  
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+34.3249P] 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         2952
_refine_ls_number_parameters     208
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0999
_refine_ls_wR_factor_ref         0.2127
_refine_ls_wR_factor_gt          0.2087
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.187
_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 0.55745(17) 0.51980(8) 0.36379(10) 0.0265(4) Uani 1 1 d . . . . .
Zn2 Zn -0.09022(16) 0.59433(8) 0.06513(10) 0.0255(4) Uani 1 1 d . . . . .
N1 N 0.5701(11) 0.3962(5) 0.4508(7) 0.033(2) Uani 1 1 d . . . . .
O4 O 0.8488(12) 0.6457(5) 0.2054(7) 0.055(3) Uani 1 1 d . . . . .
N7 N 0.1264(11) 0.5458(6) 0.1242(6) 0.032(2) Uani 1 1 d . . . . .
N6 N 0.1773(10) 0.4585(6) 0.0909(7) 0.0298(19) Uani 1 1 d . . . . .
O2 O 0.7120(10) 0.6101(5) 0.3247(7) 0.047(2) Uani 1 1 d . . . . .
N2 N 0.4965(11) 0.3751(6) 0.5343(6) 0.0303(19) Uani 1 1 d . . . . .
N3 N 0.5681(12) 0.2372(6) 0.4713(7) 0.037(2) Uani 1 1 d . . . . .
O3 O 0.8021(13) 0.4705(5) 0.1201(7) 0.057(3) Uani 1 1 d . . . . .
O1 O 0.6730(13) 0.4340(5) 0.2457(7) 0.058(3) Uani 1 1 d . . . . .
N5 N 0.3565(12) 0.5128(7) 0.2374(7) 0.042(2) Uani 1 1 d . . . . .
C2 C 0.7653(13) 0.5901(7) 0.2446(9) 0.034(2) Uani 1 1 d . . . . .
N4 N 0.4432(15) 0.2312(6) 0.6172(8) 0.056(3) Uani 1 1 d . . . . .
H4A H 0.4030 0.2624 0.6645 0.067 Uiso 1 1 calc R U . . .
H4B H 0.4475 0.1678 0.6187 0.067 Uiso 1 1 calc R U . . .
C3 C 0.6103(16) 0.3130(7) 0.4169(9) 0.040(3) Uani 1 1 d . . . . .
H3 H 0.6632 0.3065 0.3604 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2361(13) 0.5751(8) 0.2121(8) 0.035(2) Uani 1 1 d . . . . .
C4 C 0.4981(13) 0.2803(7) 0.5427(8) 0.030(2) Uani 1 1 d . . . . .
C1 C 0.7448(14) 0.4896(8) 0.1993(8) 0.036(3) Uani 1 1 d . . . . .
C6 C 0.3151(14) 0.4423(8) 0.1596(8) 0.038(3) Uani 1 1 d . . . . .
N8 N 0.405(2) 0.3546(13) 0.1498(15) 0.038(5) Uiso 0.507(19) 1 d . . P A 1
H8A H 0.3671 0.3119 0.0973 0.045 Uiso 0.507(19) 1 calc R U P A 1
H8B H 0.4966 0.3454 0.1964 0.045 Uiso 0.507(19) 1 calc R U P A 1
N9 N 0.219(3) 0.6633(15) 0.2670(17) 0.049(6) Uiso 0.493(19) 1 d . . P A 2
H9A H 0.1350 0.6984 0.2425 0.059 Uiso 0.493(19) 1 calc R U P A 2
H9B H 0.2919 0.6825 0.3253 0.059 Uiso 0.493(19) 1 calc R U P A 2
O100 O 0.478(4) 0.371(2) 0.968(2) 0.094(11) Uiso 0.428(19) 1 d D U P B 1
H100 H 0.5525 0.4025 0.9576 0.140 Uiso 0.428(19) 1 calc R U P B 1
C101 C 0.525(7) 0.277(3) 0.998(5) 0.127(17) Uiso 0.428(19) 1 d D U P B 1
H10A H 0.4376 0.2404 1.0123 0.152 Uiso 0.428(19) 1 calc R U P B 1
H10B H 0.6086 0.2784 1.0687 0.152 Uiso 0.428(19) 1 calc R U P B 1
C100 C 0.585(11) 0.222(7) 0.908(7) 0.21(3) Uiso 0.428(19) 1 d D U P B 1
H10C H 0.5303 0.2455 0.8337 0.311 Uiso 0.428(19) 1 calc R U P B 1
H10D H 0.5669 0.1529 0.9133 0.311 Uiso 0.428(19) 1 calc R U P B 1
H10E H 0.6961 0.2340 0.9209 0.311 Uiso 0.428(19) 1 calc R U P B 1
O200 O 0.490(4) 0.189(2) 1.010(3) 0.143(12) Uiso 0.572(19) 1 d D U P B 2
H200 H 0.5703 0.1760 1.0607 0.215 Uiso 0.572(19) 1 calc R U P B 2
C201 C 0.521(5) 0.185(2) 0.905(3) 0.093(11) Uiso 0.572(19) 1 d D U P B 2
H20A H 0.6020 0.2332 0.9021 0.112 Uiso 0.572(19) 1 calc R U P B 2
H20B H 0.4271 0.2005 0.8455 0.112 Uiso 0.572(19) 1 calc R U P B 2
C200 C 0.578(4) 0.0834(19) 0.890(3) 0.079(9) Uiso 0.572(19) 1 d D U P B 2
H20C H 0.6525 0.0626 0.9584 0.118 Uiso 0.572(19) 1 calc R U P B 2
H20D H 0.6268 0.0832 0.8279 0.118 Uiso 0.572(19) 1 calc R U P B 2
H20E H 0.4896 0.0390 0.8725 0.118 Uiso 0.572(19) 1 calc R U P B 2


_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 N1 2.013(8) . ?
Zn1 O2 2.021(8) . ?
Zn1 N5 2.056(9) . ?
Zn1 N2 2.069(8) 3_666 ?
Zn1 O1 2.334(8) . ?
Zn2 N7 2.005(9) . ?
Zn2 N6 2.024(8) 3_565 ?
Zn2 N3 2.053(8) 2 ?
Zn2 O4 2.083(8) 1_455 ?
Zn2 O3 2.168(8) 1_455 ?
N1 C3 1.310(13) . ?
N1 N2 1.400(11) . ?
O4 C2 1.260(13) . ?
O4 Zn2 2.083(8) 1_655 ?
N7 C5 1.325(13) . ?
N7 N6 1.393(11) . ?
N6 C6 1.323(14) . ?
N6 Zn2 2.024(8) 3_565 ?
O2 C2 1.243(13) . ?
N2 C4 1.318(12) . ?
N2 Zn1 2.069(8) 3_666 ?
N3 C4 1.354(13) . ?
N3 C3 1.356(12) . ?
N3 Zn2 2.053(8) 2_545 ?
O3 C1 1.254(13) . ?
O3 Zn2 2.168(8) 1_655 ?
O1 C1 1.239(13) . ?
N5 C5 1.354(15) . ?
N5 C6 1.355(14) . ?
C2 C1 1.496(14) . ?
N4 C4 1.343(13) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C3 H3 0.9500 . ?
C5 N9 1.43(2) . ?
C6 N8 1.48(2) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
O100 C101 1.39(2) . ?
O100 H100 0.8400 . ?
C101 C100 1.56(2) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C100 H10C 0.9800 . ?
C100 H10D 0.9800 . ?
C100 H10E 0.9800 . ?
O200 C201 1.408(19) . ?
O200 H200 0.8400 . ?
C201 C200 1.531(19) . ?
C201 H20A 0.9900 . ?
C201 H20B 0.9900 . ?
C200 H20C 0.9800 . ?
C200 H20D 0.9800 . ?
C200 H20E 0.9800 . ?

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
N1 Zn1 O2 135.3(4) . . ?
N1 Zn1 N5 106.4(4) . . ?
O2 Zn1 N5 111.4(4) . . ?
N1 Zn1 N2 105.1(3) . 3_666 ?
O2 Zn1 N2 89.9(3) . 3_666 ?
N5 Zn1 N2 101.5(4) . 3_666 ?
N1 Zn1 O1 86.1(3) . . ?
O2 Zn1 O1 73.6(3) . . ?
N5 Zn1 O1 86.7(4) . . ?
N2 Zn1 O1 163.3(3) 3_666 . ?
N7 Zn2 N6 108.6(3) . 3_565 ?
N7 Zn2 N3 105.3(4) . 2 ?
N6 Zn2 N3 100.0(3) 3_565 2 ?
N7 Zn2 O4 104.7(4) . 1_455 ?
N6 Zn2 O4 143.4(4) 3_565 1_455 ?
N3 Zn2 O4 85.2(3) 2 1_455 ?
N7 Zn2 O3 95.1(4) . 1_455 ?
N6 Zn2 O3 85.6(3) 3_565 1_455 ?
N3 Zn2 O3 155.6(4) 2 1_455 ?
O4 Zn2 O3 76.7(3) 1_455 1_455 ?
C3 N1 N2 106.1(8) . . ?
C3 N1 Zn1 124.0(7) . . ?
N2 N1 Zn1 127.2(6) . . ?
C2 O4 Zn2 115.4(7) . 1_655 ?
C5 N7 N6 106.2(9) . . ?
C5 N7 Zn2 129.5(7) . . ?
N6 N7 Zn2 123.1(6) . . ?
C6 N6 N7 106.3(8) . . ?
C6 N6 Zn2 127.8(7) . 3_565 ?
N7 N6 Zn2 121.6(6) . 3_565 ?
C2 O2 Zn1 119.2(7) . . ?
C4 N2 N1 105.6(8) . . ?
C4 N2 Zn1 130.8(7) . 3_666 ?
N1 N2 Zn1 122.6(6) . 3_666 ?
C4 N3 C3 102.8(8) . . ?
C4 N3 Zn2 131.2(7) . 2_545 ?
C3 N3 Zn2 125.6(7) . 2_545 ?
C1 O3 Zn2 112.9(7) . 1_655 ?
C1 O1 Zn1 110.3(7) . . ?
C5 N5 C6 104.1(9) . . ?
C5 N5 Zn1 129.3(7) . . ?
C6 N5 Zn1 126.7(9) . . ?
O2 C2 O4 124.6(10) . . ?
O2 C2 C1 118.2(9) . . ?
O4 C2 C1 116.8(9) . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N1 C3 N3 112.7(9) . . ?
N1 C3 H3 123.6 . . ?
N3 C3 H3 123.6 . . ?
N7 C5 N5 111.7(9) . . ?
N7 C5 N9 120.3(13) . . ?
N5 C5 N9 128.0(13) . . ?
N2 C4 N4 124.2(9) . . ?
N2 C4 N3 112.7(9) . . ?
N4 C4 N3 123.0(9) . . ?
O1 C1 O3 127.2(10) . . ?
O1 C1 C2 115.6(9) . . ?
O3 C1 C2 117.1(9) . . ?
N6 C6 N5 111.7(11) . . ?
N6 C6 N8 121.6(11) . . ?
N5 C6 N8 126.7(12) . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C5 N9 H9A 120.0 . . ?
C5 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C101 O100 H100 109.5 . . ?
O100 C101 C100 114(5) . . ?
O100 C101 H10A 108.9 . . ?
C100 C101 H10A 108.9 . . ?
O100 C101 H10B 108.9 . . ?
C100 C101 H10B 108.9 . . ?
H10A C101 H10B 107.7 . . ?
C101 C100 H10C 109.5 . . ?
C101 C100 H10D 109.5 . . ?
H10C C100 H10D 109.5 . . ?
C101 C100 H10E 109.5 . . ?
H10C C100 H10E 109.5 . . ?
H10D C100 H10E 109.5 . . ?
C201 O200 H200 109.5 . . ?
O200 C201 C200 108(3) . . ?
O200 C201 H20A 110.2 . . ?
C200 C201 H20A 110.2 . . ?
O200 C201 H20B 110.2 . . ?
C200 C201 H20B 110.2 . . ?
H20A C201 H20B 108.5 . . ?
C201 C200 H20C 109.5 . . ?
C201 C200 H20D 109.5 . . ?
H20C C200 H20D 109.5 . . ?
C201 C200 H20E 109.5 . . ?
H20C C200 H20E 109.5 . . ?
H20D C200 H20E 109.5 . . ?

_refine_diff_density_max         1.374
_refine_diff_density_min         -1.105
_refine_diff_density_rms         0.189

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_trial1_a_EtOH_squeezed
_database_code_depnum_ccdc_archive 'CCDC 1438586'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Zinc aminotriazolato oxalate'
_chemical_name_common            'Zinc aminotriazolato oxalate'
_chemical_melting_point          ?
_chemical_formula_moiety         Zn2(C2O4)(C2H3N4)2
_chemical_formula_sum            'C6 H5 N8 O4 Zn2'
_chemical_formula_weight         383.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   8.9818(10)
_cell_length_b                   13.8656(13)
_cell_length_c                   12.4104(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.360(5)
_cell_angle_gamma                90
_cell_volume                     1490.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      73.21

_exptl_crystal_description       'hexagonal plates'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.220
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5594
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   'SADABS;Universitat Gottingen,1997'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         Micro-focus
_diffrn_radiation_monochromator  Micro-focus
_diffrn_measurement_device_type  'D8 Venture APEX-II'
_diffrn_measurement_method       'CMOS-Photon 100'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19147
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.881
_diffrn_reflns_theta_max         74.394
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2952
_reflns_number_gt                2649
_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.
  
  The structure has been solved in P21/n. 
 Unfortunately the crystals were considerably twinned.
 This resulted in spurious diffraction spots adjacent
 to the metal.  
 The solvent ethanol molecule is disordered and has been modeled
 over two sites and with half-occupancy. 

 A squeeze routine (PLATON, 40 M- version 290610, A.L.Spek, 1980-2010)
 showed slight improvement in the R-values and the E- count/cell was
 119e-/cell accounting for 4.5 EtOH per unit cell. However, this is 
 overestimated compared to the analytical results and this could be 
 due to the spurious e- density from the twinning interfering with the
 'Squeeze' routine.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+25.3521P] 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         2952
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1814
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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 0.55746(14) 0.51982(7) 0.36378(8) 0.0266(3) Uani 1 1 d . . . . .
Zn2 Zn -0.09022(14) 0.59433(7) 0.06512(8) 0.0258(3) Uani 1 1 d . . . . .
N1 N 0.5706(10) 0.3962(5) 0.4511(6) 0.0322(17) Uani 1 1 d . . . . .
O4 O 0.8487(11) 0.6459(5) 0.2052(7) 0.057(2) Uani 1 1 d . . . . .
N7 N 0.1266(9) 0.5458(5) 0.1241(5) 0.0311(17) Uani 1 1 d . . . . .
N6 N 0.1776(9) 0.4587(5) 0.0910(6) 0.0296(16) Uani 1 1 d . . . . .
O2 O 0.7116(9) 0.6102(5) 0.3242(6) 0.0470(18) Uani 1 1 d . . . . .
N2 N 0.4966(9) 0.3749(5) 0.5345(6) 0.0311(17) Uani 1 1 d . . . . .
N3 N 0.5688(11) 0.2374(5) 0.4716(6) 0.038(2) Uani 1 1 d . . . . .
O3 O 0.8019(11) 0.4707(5) 0.1198(6) 0.056(2) Uani 1 1 d . . . . .
O1 O 0.6735(11) 0.4342(5) 0.2461(6) 0.057(2) Uani 1 1 d . . . . .
N5 N 0.3562(10) 0.5128(6) 0.2379(6) 0.042(2) Uani 1 1 d . . . . .
C2 C 0.7652(12) 0.5902(6) 0.2449(8) 0.034(2) Uani 1 1 d . . . . .
N4 N 0.4436(13) 0.2311(5) 0.6174(7) 0.055(3) Uani 1 1 d . . . . .
H4A H 0.4039 0.2625 0.6648 0.066 Uiso 1 1 calc R U . . .
H4B H 0.4477 0.1677 0.6190 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6102(14) 0.3128(6) 0.4167(8) 0.041(3) Uani 1 1 d . . . . .
H3 H 0.6622 0.3061 0.3597 0.049 Uiso 1 1 calc R U . . .
C5 C 0.2365(11) 0.5750(7) 0.2122(7) 0.035(2) Uani 1 1 d . . . . .
C4 C 0.4982(11) 0.2801(6) 0.5425(7) 0.0296(19) Uani 1 1 d . . . . .
C1 C 0.7449(12) 0.4897(7) 0.1993(7) 0.037(2) Uani 1 1 d . . . . .
C6 C 0.3149(12) 0.4419(7) 0.1597(7) 0.038(2) Uani 1 1 d . . . . .
N8 N 0.4069(19) 0.3544(11) 0.1497(13) 0.033(4) Uiso 0.483(16) 1 d . . P A 1
H8A H 0.3700 0.3119 0.0966 0.040 Uiso 0.483(16) 1 calc R U P A 1
H8B H 0.4980 0.3453 0.1968 0.040 Uiso 0.483(16) 1 calc R U P A 1
N9 N 0.220(2) 0.6638(13) 0.2670(15) 0.052(5) Uiso 0.517(16) 1 d . . P A 2
H9A H 0.1366 0.6993 0.2423 0.063 Uiso 0.517(16) 1 calc R U P A 2
H9B H 0.2931 0.6829 0.3254 0.063 Uiso 0.517(16) 1 calc R U P A 2


_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 N1 2.015(7) . ?
Zn1 O2 2.022(7) . ?
Zn1 N5 2.054(8) . ?
Zn1 N2 2.070(7) 3_666 ?
Zn1 O1 2.331(7) . ?
Zn2 N7 2.006(8) . ?
Zn2 N6 2.026(7) 3_565 ?
Zn2 N3 2.056(7) 2 ?
Zn2 O4 2.083(7) 1_455 ?
Zn2 O3 2.165(7) 1_455 ?
N1 C3 1.314(11) . ?
N1 N2 1.401(10) . ?
O4 C2 1.263(11) . ?
O4 Zn2 2.083(7) 1_655 ?
N7 C5 1.327(11) . ?
N7 N6 1.392(9) . ?
N6 C6 1.321(12) . ?
N6 Zn2 2.026(7) 3_565 ?
O2 C2 1.236(11) . ?
N2 C4 1.318(11) . ?
N2 Zn1 2.070(7) 3_666 ?
N3 C4 1.350(11) . ?
N3 C3 1.352(11) . ?
N3 Zn2 2.056(7) 2_545 ?
O3 C1 1.253(11) . ?
O3 Zn2 2.165(7) 1_655 ?
O1 C1 1.240(11) . ?
N5 C5 1.348(13) . ?
N5 C6 1.363(12) . ?
C2 C1 1.497(12) . ?
N4 C4 1.344(11) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C3 H3 0.9500 . ?
C5 N9 1.434(19) . ?
C6 N8 1.491(18) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?

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
N1 Zn1 O2 135.4(3) . . ?
N1 Zn1 N5 106.4(3) . . ?
O2 Zn1 N5 111.4(3) . . ?
N1 Zn1 N2 105.2(3) . 3_666 ?
O2 Zn1 N2 89.9(3) . 3_666 ?
N5 Zn1 N2 101.3(3) . 3_666 ?
N1 Zn1 O1 86.1(3) . . ?
O2 Zn1 O1 73.4(3) . . ?
N5 Zn1 O1 87.1(3) . . ?
N2 Zn1 O1 163.2(3) 3_666 . ?
N7 Zn2 N6 108.6(3) . 3_565 ?
N7 Zn2 N3 105.4(3) . 2 ?
N6 Zn2 N3 100.0(3) 3_565 2 ?
N7 Zn2 O4 104.8(3) . 1_455 ?
N6 Zn2 O4 143.3(3) 3_565 1_455 ?
N3 Zn2 O4 85.1(3) 2 1_455 ?
N7 Zn2 O3 95.3(3) . 1_455 ?
N6 Zn2 O3 85.4(3) 3_565 1_455 ?
N3 Zn2 O3 155.4(3) 2 1_455 ?
O4 Zn2 O3 76.8(2) 1_455 1_455 ?
C3 N1 N2 106.1(7) . . ?
C3 N1 Zn1 123.9(6) . . ?
N2 N1 Zn1 127.2(5) . . ?
C2 O4 Zn2 115.5(6) . 1_655 ?
C5 N7 N6 106.0(7) . . ?
C5 N7 Zn2 129.6(6) . . ?
N6 N7 Zn2 123.1(5) . . ?
C6 N6 N7 106.7(7) . . ?
C6 N6 Zn2 127.7(6) . 3_565 ?
N7 N6 Zn2 121.5(5) . 3_565 ?
C2 O2 Zn1 119.4(6) . . ?
C4 N2 N1 105.5(7) . . ?
C4 N2 Zn1 131.0(6) . 3_666 ?
N1 N2 Zn1 122.4(5) . 3_666 ?
C4 N3 C3 103.2(7) . . ?
C4 N3 Zn2 131.0(6) . 2_545 ?
C3 N3 Zn2 125.4(6) . 2_545 ?
C1 O3 Zn2 113.0(6) . 1_655 ?
C1 O1 Zn1 110.5(6) . . ?
C5 N5 C6 104.1(8) . . ?
C5 N5 Zn1 129.5(6) . . ?
C6 N5 Zn1 126.5(7) . . ?
O2 C2 O4 124.7(8) . . ?
O2 C2 C1 118.4(8) . . ?
O4 C2 C1 116.5(8) . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N1 C3 N3 112.5(8) . . ?
N1 C3 H3 123.8 . . ?
N3 C3 H3 123.8 . . ?
N7 C5 N5 111.9(8) . . ?
N7 C5 N9 120.3(11) . . ?
N5 C5 N9 127.8(11) . . ?
N2 C4 N4 123.9(8) . . ?
N2 C4 N3 112.7(8) . . ?
N4 C4 N3 123.3(8) . . ?
O1 C1 O3 127.4(9) . . ?
O1 C1 C2 115.2(8) . . ?
O3 C1 C2 117.3(8) . . ?
N6 C6 N5 111.3(9) . . ?
N6 C6 N8 122.2(9) . . ?
N5 C6 N8 126.5(10) . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C5 N9 H9A 120.0 . . ?
C5 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?

_refine_diff_density_max         1.311
_refine_diff_density_min         -1.051
_refine_diff_density_rms         0.170
# SQUEEZE RESULTS (APPEND TO CIF)
# 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 0.000 0.500 0.500 208 59 ' '
2 0.500 1.000 0.000 208 59 ' '
_platon_squeeze_details          
;
;
_shelxl_version_number           2014/6


