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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_Zn1O6C3N2H8
_database_code_depnum_ccdc_archive 'CCDC 1414792'
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2015-08-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Hydrazinium zinc formate'
_chemical_formula_moiety         'C3 H3 O6 Zn, H5 N2'
_chemical_formula_sum            'C3 H8 N2 O6 Zn'
_chemical_formula_weight         233.48
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn1 O6 C3 H8 N2'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.29731(6)
_cell_length_b                   7.94804(7)
_cell_length_c                   13.82240(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     801.690(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21150
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      36.9350
_cell_measurement_theta_min      2.9490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.060
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) 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) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.6582
_exptl_crystal_size_mid          0.2766
_exptl_crystal_size_min          0.209
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            47309
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.317
_diffrn_reflns_theta_min         2.947
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1183
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0546400000
_diffrn_orient_matrix_UB_12      -0.0699273000
_diffrn_orient_matrix_UB_13      -0.0135835000
_diffrn_orient_matrix_UB_21      0.0206233000
_diffrn_orient_matrix_UB_22      0.0398123000
_diffrn_orient_matrix_UB_23      -0.0446172000
_diffrn_orient_matrix_UB_31      0.0777104000
_diffrn_orient_matrix_UB_32      0.0385656000
_diffrn_orient_matrix_UB_33      0.0214052000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3790
_reflns_number_total             3869
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1602 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(3)
_refine_ls_extinction_coef       0.0204(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0151
_refine_ls_R_factor_gt           0.0144
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0214P)²+0.0842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0373
_refine_ls_wR_factor_ref         0.0375
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All N(H,H) groups
2. Restrained distances
 H2B-N2
 0.89 with sigma of 0.001
 H2A-N2
 0.89 with sigma of 0.001
 H2B-H2A
 1.453 with sigma of 0.001
 H2B-N1
 1.916 with sigma of 0.001
 H2A-N1
 1.916 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.75924(2) 0.71943(2) 0.66453(2) 0.00636(3) Uani 1 1 d . . . . .
O2 O 0.58650(12) 0.92540(11) 0.66291(7) 0.01269(14) Uani 1 1 d . . . . .
O3 O 0.90375(12) 0.80618(11) 0.78854(6) 0.01059(14) Uani 1 1 d . . . . .
O4 O 0.60870(13) 0.60502(12) 0.77203(7) 0.01388(16) Uani 1 1 d . . . . .
O5 O 0.61923(12) 0.61081(11) 0.54686(6) 0.01136(15) Uani 1 1 d . . . . .
O6 O 0.91920(12) 0.86982(11) 0.57341(6) 0.01260(15) Uani 1 1 d . . . . .
O7 O 0.92287(12) 0.50424(11) 0.64373(6) 0.01265(15) Uani 1 1 d . . . . .
C3 C 0.50866(15) 0.69260(13) 0.49474(8) 0.01098(18) Uani 1 1 d . . . . .
H3 H 0.4925 0.8089 0.5082 0.013 Uiso 1 1 calc R . . . .
C4 C 0.50097(17) 0.98458(15) 0.73352(8) 0.01045(18) Uani 1 1 d . . . . .
H4 H 0.5205 0.9350 0.7952 0.013 Uiso 1 1 calc R . . . .
C5 C 0.99169(16) 0.94291(15) 0.78645(8) 0.01064(18) Uani 1 1 d . . . . .
H5 H 0.9929 1.0037 0.7273 0.013 Uiso 1 1 calc R . . . .
N2 N 0.68452(14) 0.21299(14) 0.53830(8) 0.01451(17) Uani 1 1 d D . . . .
N1 N 0.76572(14) 0.31745(12) 0.46381(7) 0.01194(15) Uani 1 1 d D . . . .
H1A H 0.7231 0.2849 0.4049 0.014 Uiso 1 1 calc GR . . . .
H1B H 0.8898 0.3061 0.4654 0.014 Uiso 1 1 calc GR . . . .
H1C H 0.7353 0.4269 0.4744 0.014 Uiso 1 1 calc GR . . . .
H2A H 0.7222(15) 0.2522(11) 0.59524(10) 0.018 Uiso 1 1 d DR . . . .
H2B H 0.7263(15) 0.1088(4) 0.5301(6) 0.018 Uiso 1 1 d DR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.00728(5) 0.00572(5) 0.00607(5) 0.00014(4) 0.00024(4) 0.00020(4)
O2 0.0157(3) 0.0116(3) 0.0108(3) -0.0003(3) 0.0034(3) 0.0062(3)
O3 0.0133(3) 0.0090(3) 0.0095(3) -0.0002(3) -0.0009(3) -0.0049(3)
O4 0.0164(4) 0.0148(4) 0.0104(3) 0.0004(3) 0.0013(3) -0.0095(3)
O5 0.0127(3) 0.0113(3) 0.0101(3) -0.0011(3) -0.0049(3) 0.0032(3)
O6 0.0157(4) 0.0109(3) 0.0112(3) -0.0010(3) 0.0065(3) -0.0010(3)
O7 0.0166(4) 0.0108(3) 0.0106(3) -0.0003(3) -0.0041(3) 0.0059(3)
C3 0.0130(4) 0.0091(4) 0.0108(4) -0.0012(4) -0.0042(4) 0.0020(3)
C4 0.0123(4) 0.0102(4) 0.0088(4) 0.0005(3) 0.0014(3) 0.0038(3)
C5 0.0129(4) 0.0093(4) 0.0097(4) 0.0010(3) -0.0024(3) -0.0037(3)
N2 0.0191(4) 0.0129(4) 0.0115(4) 0.0031(4) 0.0011(3) -0.0005(4)
N1 0.0143(4) 0.0110(3) 0.0106(3) 0.0004(3) 0.0008(3) 0.0005(3)

_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 O2 2.0663(8) . ?
Zn1 O3 2.1273(8) . ?
Zn1 O4 2.0595(9) . ?
Zn1 O5 2.1058(9) . ?
Zn1 O6 2.0923(9) . ?
Zn1 O7 2.1056(9) . ?
O2 C4 1.2503(14) . ?
O3 C5 1.2624(14) . ?
O4 C4 1.2501(14) 4_646 ?
O5 C3 1.2621(13) . ?
O6 C3 1.2489(13) 3_566 ?
O7 C5 1.2481(14) 4_746 ?
C3 O6 1.2489(13) 3_466 ?
C3 H3 0.9500 . ?
C4 O4 1.2501(14) 4_656 ?
C4 H4 0.9500 . ?
C5 O7 1.2481(14) 4_756 ?
C5 H5 0.9500 . ?
N2 N1 1.4493(14) . ?
N2 H2A 0.8901(14) . ?
N2 H2B 0.8896(13) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?

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
O2 Zn1 O3 93.11(4) . . ?
O2 Zn1 O5 91.17(4) . . ?
O2 Zn1 O6 83.18(4) . . ?
O2 Zn1 O7 171.12(3) . . ?
O4 Zn1 O2 91.85(4) . . ?
O4 Zn1 O3 79.99(4) . . ?
O4 Zn1 O5 96.74(3) . . ?
O4 Zn1 O6 169.78(4) . . ?
O4 Zn1 O7 92.43(4) . . ?
O5 Zn1 O3 174.69(3) . . ?
O6 Zn1 O3 91.34(3) . . ?
O6 Zn1 O5 92.29(3) . . ?
O6 Zn1 O7 93.76(4) . . ?
O7 Zn1 O3 95.29(3) . . ?
O7 Zn1 O5 80.60(3) . . ?
C4 O2 Zn1 126.45(8) . . ?
C5 O3 Zn1 120.84(8) . . ?
C4 O4 Zn1 129.45(8) 4_646 . ?
C3 O5 Zn1 122.68(7) . . ?
C3 O6 Zn1 121.25(8) 3_566 . ?
C5 O7 Zn1 119.67(8) 4_746 . ?
O5 C3 H3 118.0 . . ?
O6 C3 O5 124.07(10) 3_466 . ?
O6 C3 H3 118.0 3_466 . ?
O2 C4 H4 118.0 . . ?
O4 C4 O2 124.04(11) 4_656 . ?
O4 C4 H4 118.0 4_656 . ?
O3 C5 H5 117.5 . . ?
O7 C5 O3 124.92(11) 4_756 . ?
O7 C5 H5 117.5 4_756 . ?
N1 N2 H2A 107.54(18) . . ?
N1 N2 H2B 107.60(18) . . ?
H2A N2 H2B 109.5(2) . . ?
N2 N1 H1A 109.5 . . ?
N2 N1 H1B 109.5 . . ?
N2 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?

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
N1 H1A O3 0.91 1.99 2.8921(13) 170.2 2_664
N1 H1C O5 0.91 1.96 2.8102(13) 154.1 .

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -8 13 0.0967 0.0000 -8.0000 12.9999 0.3828 -0.8985 -0.0303
0 9 -12 0.1036 -0.0000 9.0000 -11.9998 -0.4663 0.8937 0.0902
-7 -8 -3 0.2667 -7.0000 -8.0000 -3.0001 0.2177 -0.3290 -0.9167
7 8 3 0.2182 7.0000 8.0000 3.0001 -0.2177 0.3290 0.9167
0 -6 -17 0.1314 -0.0000 -6.0000 -17.0001 0.6505 0.5196 -0.5953
-1 6 17 0.1670 -1.0000 6.0000 17.0001 -0.7051 -0.5402 0.5176
9 -2 -10 0.2067 9.0000 -2.0000 -10.0001 0.7675 0.5522 0.4082
8 5 9 0.2618 8.0000 5.0000 9.0000 -0.0348 -0.0375 1.0072
-10 -2 2 0.3664 -10.0000 -2.0000 2.0000 -0.4337 -0.3751 -0.8114
-9 2 10 0.3431 -9.0000 2.0000 10.0001 -0.7675 -0.5522 -0.4082
8 7 -4 0.1820 8.0000 7.0000 -3.9999 0.0020 0.6221 0.8060
5 6 -14 0.1472 5.0000 6.0000 -13.9999 0.0438 0.9666 0.3203
0 3 -19 0.1436 -0.0000 3.0000 -18.9999 0.0483 0.9672 -0.2910
-8 -7 4 0.2744 -8.0000 -7.0000 3.9999 -0.0020 -0.6221 -0.8060
0 11 -6 0.1006 -0.0000 11.0000 -5.9998 -0.6877 0.7056 0.2958
-2 10 -8 0.1267 -2.0000 10.0000 -7.9998 -0.6999 0.7138 0.0590
6 9 3 0.1799 6.0000 9.0000 3.0001 -0.3423 0.3482 0.8776
0 10 9 0.1105 -0.0000 10.0000 9.0002 -0.8215 -0.0034 0.5783
0 -10 -9 0.1423 0.0000 -10.0000 -9.0002 0.8215 0.0034 -0.5783
-10 3 -1 0.3614 -10.0000 3.0000 -0.9999 -0.7426 -0.0422 -0.6828
-4 9 7 0.2186 -4.0000 9.0000 7.0002 -0.9430 -0.0365 0.1861
0 4 18 0.1451 0.0000 4.0000 18.0001 -0.5242 -0.6439 0.5396
-7 1 14 0.2958 -7.0000 1.0000 14.0000 -0.6426 -0.7292 -0.2057
-9 -1 10 0.3235 -9.0000 -1.0000 10.0000 -0.5577 -0.6716 -0.5239
-6 -7 8 0.2164 -6.0000 -7.0000 7.9999 0.0530 -0.7594 -0.5650
-8 -5 -8 0.3148 -8.0000 -5.0000 -8.0000 0.0212 -0.0071 -0.9858
5 -8 8 0.2043 5.0000 -8.0000 7.9998 0.7240 -0.5723 0.2513
0 -11 3 0.1332 0.0000 -11.0000 2.9998 0.7285 -0.5718 -0.3600

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    Moisture-sensitive
