# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1446959'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H7 N5 O5 P Zn1.50'
_chemical_formula_weight         310.15

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.1355(5)
_cell_length_b                   10.3100(13)
_cell_length_c                   14.9951(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.076(3)
_cell_angle_gamma                90.00
_cell_volume                     793.42(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1323
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.52

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    4.783
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7104
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         27.54
_reflns_number_total             1819
_reflns_number_gt                1416
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    Diamond
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0399P)²+4.9437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1819
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.66664(13) -0.44637(7) 0.39967(4) 0.0111(2) Uani 1 1 d . . .
Zn2 Zn 1.0000 -0.5000 0.0000 0.0130(2) Uani 1 2 d S . .
P1 P 1.1745(3) -0.31485(15) 0.48720(10) 0.0098(3) Uani 1 1 d . . .
O1 O 0.8776(8) -0.3309(4) 0.4742(3) 0.0146(9) Uani 1 1 d . . .
O2 O 1.2346(7) -0.1694(4) 0.4875(3) 0.0151(9) Uani 1 1 d . . .
O3 O 1.2689(9) -0.3733(4) 0.5769(3) 0.0172(10) Uani 1 1 d . . .
O4 O 1.3092(8) -0.3849(4) 0.4109(3) 0.0163(10) Uani 1 1 d . . .
N1 N 0.7266(9) -0.4140(5) 0.2694(3) 0.0143(11) Uani 1 1 d . . .
N2 N 0.8595(10) -0.4359(5) 0.1286(3) 0.0178(12) Uani 1 1 d . . .
N3 N 0.6544(11) -0.3479(6) 0.1331(3) 0.0207(13) Uani 1 1 d . . .
H1 H 0.6143 -0.3070 0.0899 0.050 Uiso 1 1 d . . .
N4 N 1.0744(10) -0.5603(6) 0.2433(3) 0.0214(13) Uani 1 1 d . . .
H2 H 1.1321 -0.5561 0.3035 0.050 Uiso 1 1 d . . .
H3 H 1.1731 -0.5802 0.1894 0.050 Uiso 1 1 d . . .
N5 N 0.3919(11) -0.2567(6) 0.2425(4) 0.0247(13) Uani 1 1 d . . .
H4 H 0.3278 -0.2721 0.2981 0.050 Uiso 1 1 d . . .
H5 H 0.2912 -0.2151 0.2104 0.050 Uiso 1 1 d . . .
C1 C 0.8964(12) -0.4713(6) 0.2127(4) 0.0130(13) Uani 1 1 d . . .
C2 C 0.5789(12) -0.3368(6) 0.2161(4) 0.0153(13) Uani 1 1 d . . .
OW1 O 1.3020(8) -0.5988(4) 0.0703(3) 0.0168(10) Uani 1 1 d . . .
H6 H 1.3031 -0.6816 0.0790 0.050 Uiso 1 1 d . . .
H7 H 1.4905 -0.6028 0.0841 0.050 Uiso 1 1 d . . .

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 0.0128(3) 0.0110(4) 0.0094(3) -0.0005(3) 0.0000(2) 0.0010(3)
Zn2 0.0128(5) 0.0133(5) 0.0130(5) -0.0004(4) 0.0016(4) 0.0009(4)
P1 0.0109(7) 0.0091(8) 0.0093(7) -0.0005(6) -0.0003(5) 0.0003(6)
O1 0.0110(19) 0.011(2) 0.022(2) -0.0039(18) 0.0011(17) 0.0019(18)
O2 0.0096(19) 0.009(2) 0.027(2) -0.0010(18) 0.0019(17) -0.0004(17)
O3 0.029(2) 0.014(2) 0.008(2) 0.0009(17) -0.0056(17) 0.003(2)
O4 0.014(2) 0.021(3) 0.014(2) -0.0021(18) 0.0032(17) 0.0031(19)
N1 0.013(2) 0.018(3) 0.012(2) 0.002(2) 0.0025(19) 0.004(2)
N2 0.022(3) 0.020(3) 0.012(3) 0.001(2) 0.002(2) 0.008(2)
N3 0.031(3) 0.026(3) 0.005(2) 0.004(2) 0.003(2) 0.014(3)
N4 0.020(3) 0.031(4) 0.013(3) 0.004(2) -0.001(2) 0.008(3)
N5 0.026(3) 0.032(4) 0.017(3) 0.007(3) 0.006(2) 0.017(3)
C1 0.015(3) 0.010(3) 0.014(3) -0.002(2) 0.004(2) 0.002(2)
C2 0.018(3) 0.009(3) 0.019(3) 0.002(2) 0.002(2) 0.002(3)
OW1 0.014(2) 0.016(2) 0.020(2) 0.0004(19) -0.0015(17) 0.0019(19)

_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 O3 1.918(4) 3_746 ?
Zn1 O1 1.937(4) . ?
Zn1 O4 1.955(4) 1_455 ?
Zn1 N1 2.017(5) . ?
Zn2 OW1 2.107(4) 3_745 ?
Zn2 OW1 2.107(4) . ?
Zn2 O2 2.134(4) 4 ?
Zn2 O2 2.134(4) 2_745 ?
Zn2 N2 2.186(5) . ?
Zn2 N2 2.186(5) 3_745 ?
P1 O2 1.531(4) . ?
P1 O3 1.537(4) . ?
P1 O4 1.538(4) . ?
P1 O1 1.539(4) . ?
O2 Zn2 2.134(4) 2_755 ?
O3 Zn1 1.918(4) 3_746 ?
O4 Zn1 1.955(4) 1_655 ?
N1 C2 1.343(8) . ?
N1 C1 1.374(8) . ?
N2 C1 1.319(8) . ?
N2 N3 1.394(7) . ?
N3 C2 1.322(8) . ?
N3 H1 0.7934 . ?
N4 C1 1.363(8) . ?
N4 H2 0.9407 . ?
N4 H3 0.9910 . ?
N5 C2 1.337(8) . ?
N5 H4 0.9218 . ?
N5 H5 0.8151 . ?
OW1 H6 0.8632 . ?
OW1 H7 0.9833 . ?

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
O3 Zn1 O1 113.64(17) 3_746 . ?
O3 Zn1 O4 117.1(2) 3_746 1_455 ?
O1 Zn1 O4 104.97(18) . 1_455 ?
O3 Zn1 N1 107.8(2) 3_746 . ?
O1 Zn1 N1 110.8(2) . . ?
O4 Zn1 N1 101.93(19) 1_455 . ?
OW1 Zn2 OW1 180.0 3_745 . ?
OW1 Zn2 O2 88.15(16) 3_745 4 ?
OW1 Zn2 O2 91.85(16) . 4 ?
OW1 Zn2 O2 91.85(16) 3_745 2_745 ?
OW1 Zn2 O2 88.15(16) . 2_745 ?
O2 Zn2 O2 180.0(2) 4 2_745 ?
OW1 Zn2 N2 92.01(18) 3_745 . ?
OW1 Zn2 N2 87.99(18) . . ?
O2 Zn2 N2 92.03(19) 4 . ?
O2 Zn2 N2 87.97(19) 2_745 . ?
OW1 Zn2 N2 87.99(18) 3_745 3_745 ?
OW1 Zn2 N2 92.01(18) . 3_745 ?
O2 Zn2 N2 87.97(19) 4 3_745 ?
O2 Zn2 N2 92.03(19) 2_745 3_745 ?
N2 Zn2 N2 179.999(1) . 3_745 ?
O2 P1 O3 108.9(2) . . ?
O2 P1 O4 111.5(3) . . ?
O3 P1 O4 109.3(2) . . ?
O2 P1 O1 107.7(2) . . ?
O3 P1 O1 110.4(3) . . ?
O4 P1 O1 109.0(2) . . ?
P1 O1 Zn1 132.1(3) . . ?
P1 O2 Zn2 133.4(2) . 2_755 ?
P1 O3 Zn1 126.0(3) . 3_746 ?
P1 O4 Zn1 131.7(2) . 1_655 ?
C2 N1 C1 104.1(5) . . ?
C2 N1 Zn1 124.9(4) . . ?
C1 N1 Zn1 130.6(4) . . ?
C1 N2 N3 102.5(5) . . ?
C1 N2 Zn2 135.9(4) . . ?
N3 N2 Zn2 120.9(4) . . ?
C2 N3 N2 110.4(5) . . ?
C2 N3 H1 130.3 . . ?
N2 N3 H1 118.7 . . ?
C1 N4 H2 118.5 . . ?
C1 N4 H3 102.8 . . ?
H2 N4 H3 129.8 . . ?
C2 N5 H4 116.4 . . ?
C2 N5 H5 126.7 . . ?
H4 N5 H5 112.6 . . ?
N2 C1 N4 125.4(6) . . ?
N2 C1 N1 113.6(5) . . ?
N4 C1 N1 120.9(5) . . ?
N3 C2 N5 124.8(6) . . ?
N3 C2 N1 109.3(5) . . ?
N5 C2 N1 125.9(6) . . ?
Zn2 OW1 H6 123.6 . . ?
Zn2 OW1 H7 145.7 . . ?
H6 OW1 H7 85.8 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.598
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.188
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1446960'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H5 N5 O4 P Zn1.50'
_chemical_formula_weight         292.14

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.9644(15)
_cell_length_b                   5.2062(4)
_cell_length_c                   16.2282(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.958(6)
_cell_angle_gamma                90.00
_cell_volume                     1464.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1391
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      23.45

_exptl_crystal_description       needle
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    5.165
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12614
_diffrn_reflns_av_R_equivalents  0.1234
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.54
_reflns_number_total             1678
_reflns_number_gt                1203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    Diamond
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0488P)²+26.9654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1678
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.31852(5) 0.43632(17) 0.46742(6) 0.0158(3) Uani 1 1 d . . .
Zn2 Zn 0.5000 0.2194(3) 0.2500 0.0184(3) Uani 1 2 d S . .
P1 P 0.35316(11) -0.0663(4) 0.58408(13) 0.0137(4) Uani 1 1 d . . .
O1 O 0.3424(3) 0.0731(11) 0.4968(4) 0.0222(12) Uani 1 1 d . . .
O2 O 0.4302(3) 0.0165(10) 0.6604(4) 0.0193(12) Uani 1 1 d . . .
O3 O 0.3564(3) -0.3547(10) 0.5726(4) 0.0238(13) Uani 1 1 d . . .
O4 O 0.2887(3) 0.0086(11) 0.6131(4) 0.0222(13) Uani 1 1 d . . .
N1 N 0.3711(4) 0.5055(13) 0.3820(5) 0.0179(14) Uani 1 1 d . . .
N2 N 0.3959(4) 0.6336(13) 0.2680(5) 0.0217(15) Uani 1 1 d . . .
H1 H 0.3917 0.7286 0.2168 0.050 Uiso 1 1 d . . .
N3 N 0.4427(4) 0.4271(14) 0.3048(5) 0.0212(15) Uani 1 1 d . . .
N4 N 0.3005(4) 0.8623(15) 0.2963(5) 0.0294(18) Uani 1 1 d . . .
H2 H 0.2869 0.9534 0.2418 0.050 Uiso 1 1 d . . .
H3 H 0.2814 0.9074 0.3349 0.050 Uiso 1 1 d . . .
N5 N 0.4598(4) 0.1618(15) 0.4288(5) 0.0300(18) Uani 1 1 d . . .
H4 H 0.4815 0.0358 0.4024 0.050 Uiso 1 1 d . . .
H5 H 0.4489 0.0736 0.4757 0.050 Uiso 1 1 d . . .
C1 C 0.3532(5) 0.6776(16) 0.3136(5) 0.0195(17) Uani 1 1 d . . .
C2 C 0.4255(4) 0.3568(16) 0.3726(5) 0.0200(17) Uani 1 1 d . . .

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 0.0188(5) 0.0129(5) 0.0192(5) 0.0003(4) 0.0112(4) 0.0010(4)
Zn2 0.0183(7) 0.0178(7) 0.0234(7) 0.000 0.0130(6) 0.000
P1 0.0145(9) 0.0120(10) 0.0158(9) -0.0012(8) 0.0074(7) 0.0000(8)
O1 0.032(3) 0.014(3) 0.022(3) 0.007(2) 0.012(2) 0.005(2)
O2 0.020(3) 0.014(3) 0.023(3) -0.001(2) 0.008(2) 0.000(2)
O3 0.039(3) 0.009(3) 0.024(3) -0.002(2) 0.013(3) 0.001(2)
O4 0.015(3) 0.035(4) 0.019(3) -0.002(2) 0.009(2) 0.003(2)
N1 0.018(3) 0.018(4) 0.023(4) 0.004(3) 0.014(3) 0.003(3)
N2 0.035(4) 0.013(4) 0.026(4) 0.008(3) 0.022(3) 0.007(3)
N3 0.023(3) 0.023(4) 0.024(4) 0.007(3) 0.017(3) 0.007(3)
N4 0.036(4) 0.023(4) 0.033(4) 0.008(3) 0.018(4) 0.014(3)
N5 0.039(4) 0.027(4) 0.035(4) 0.018(3) 0.026(4) 0.018(3)
C1 0.022(4) 0.016(4) 0.022(4) -0.002(3) 0.011(3) 0.003(3)
C2 0.019(4) 0.025(5) 0.019(4) 0.006(3) 0.011(3) 0.003(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 O3 1.901(6) 1_565 ?
Zn1 O4 1.941(5) 7_556 ?
Zn1 O1 1.958(6) . ?
Zn1 N1 2.041(6) . ?
Zn2 O2 1.952(6) 6 ?
Zn2 O2 1.952(6) 5_656 ?
Zn2 N3 1.982(6) . ?
Zn2 N3 1.982(6) 2_655 ?
P1 O3 1.518(6) . ?
P1 O4 1.528(5) . ?
P1 O1 1.529(6) . ?
P1 O2 1.545(6) . ?
O2 Zn2 1.952(6) 5_656 ?
O3 Zn1 1.901(6) 1_545 ?
O4 Zn1 1.941(5) 7_556 ?
N1 C2 1.348(10) . ?
N1 C1 1.358(10) . ?
N2 C1 1.319(10) . ?
N2 N3 1.367(9) . ?
N2 H1 0.9423 . ?
N3 C2 1.318(10) . ?
N4 C1 1.332(10) . ?
N4 H2 0.9428 . ?
N4 H3 0.8736 . ?
N5 C2 1.343(10) . ?
N5 H4 0.9620 . ?
N5 H5 0.9806 . ?

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
O3 Zn1 O4 115.5(2) 1_565 7_556 ?
O3 Zn1 O1 111.6(2) 1_565 . ?
O4 Zn1 O1 112.5(3) 7_556 . ?
O3 Zn1 N1 113.4(3) 1_565 . ?
O4 Zn1 N1 100.6(2) 7_556 . ?
O1 Zn1 N1 102.0(2) . . ?
O2 Zn2 O2 102.0(3) 6 5_656 ?
O2 Zn2 N3 110.4(3) 6 . ?
O2 Zn2 N3 109.8(3) 5_656 . ?
O2 Zn2 N3 109.8(3) 6 2_655 ?
O2 Zn2 N3 110.4(3) 5_656 2_655 ?
N3 Zn2 N3 113.9(4) . 2_655 ?
O3 P1 O4 111.6(3) . . ?
O3 P1 O1 110.6(3) . . ?
O4 P1 O1 110.0(3) . . ?
O3 P1 O2 107.6(3) . . ?
O4 P1 O2 107.3(3) . . ?
O1 P1 O2 109.7(3) . . ?
P1 O1 Zn1 127.9(3) . . ?
P1 O2 Zn2 123.8(3) . 5_656 ?
P1 O3 Zn1 131.1(4) . 1_545 ?
P1 O4 Zn1 125.5(3) . 7_556 ?
C2 N1 C1 103.5(6) . . ?
C2 N1 Zn1 125.7(5) . . ?
C1 N1 Zn1 130.0(5) . . ?
C1 N2 N3 109.2(6) . . ?
C1 N2 H1 123.5 . . ?
N3 N2 H1 127.3 . . ?
C2 N3 N2 104.3(6) . . ?
C2 N3 Zn2 126.1(6) . . ?
N2 N3 Zn2 127.6(5) . . ?
C1 N4 H2 117.2 . . ?
C1 N4 H3 122.5 . . ?
H2 N4 H3 120.1 . . ?
C2 N5 H4 112.9 . . ?
C2 N5 H5 133.2 . . ?
H4 N5 H5 106.8 . . ?
N2 C1 N4 125.9(8) . . ?
N2 C1 N1 109.7(7) . . ?
N4 C1 N1 124.4(7) . . ?
N3 C2 N5 124.1(7) . . ?
N3 C2 N1 113.3(7) . . ?
N5 C2 N1 122.6(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.352
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.221
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1446961'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H5 N5 O4 P Zn1.50'
_chemical_formula_weight         292.14

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   19.0043(6)
_cell_length_b                   5.2056(2)
_cell_length_c                   16.2524(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.018(2)
_cell_angle_gamma                90.00
_cell_volume                     1468.62(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    5.150
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9884
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.56
_reflns_number_total             1676
_reflns_number_gt                1426
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    Diamond
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0293P)²+1.6553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1676
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.318602(18) 0.43632(6) 0.46716(2) 0.01336(11) Uani 1 1 d . . .
Zn2 Zn 0.5000 0.21882(9) 0.2500 0.01561(13) Uani 1 2 d S . .
P1 P 0.35317(4) -0.06647(14) 0.58401(5) 0.01067(16) Uani 1 1 d . . .
O1 O 0.34233(12) 0.0739(4) 0.49621(14) 0.0162(4) Uani 1 1 d . . .
O2 O 0.43018(11) 0.0173(4) 0.66025(14) 0.0161(4) Uani 1 1 d . . .
O3 O 0.35645(13) -0.3543(4) 0.57223(14) 0.0202(5) Uani 1 1 d . . .
O4 O 0.28865(11) 0.0087(4) 0.61284(14) 0.0204(5) Uani 1 1 d . . .
N1 N 0.37080(13) 0.5057(5) 0.38180(17) 0.0155(5) Uani 1 1 d . . .
N2 N 0.39557(15) 0.6332(5) 0.26816(17) 0.0201(6) Uani 1 1 d . . .
H1 H 0.3917 0.7286 0.2168 0.050 Uiso 1 1 d . . .
N3 N 0.44284(15) 0.4246(5) 0.30513(18) 0.0201(6) Uani 1 1 d . . .
N4 N 0.30045(16) 0.8626(6) 0.29618(19) 0.0265(6) Uani 1 1 d . . .
H2 H 0.2869 0.9534 0.2418 0.050 Uiso 1 1 d . . .
H3 H 0.2814 0.9074 0.3349 0.050 Uiso 1 1 d . . .
N5 N 0.45930(17) 0.1599(6) 0.4282(2) 0.0309(7) Uani 1 1 d . . .
H4 H 0.4871 0.0645 0.4098 0.050 Uiso 1 1 d . . .
H5 H 0.4275 0.0962 0.4546 0.050 Uiso 1 1 d . . .
C1 C 0.35392(17) 0.6784(6) 0.3149(2) 0.0166(6) Uani 1 1 d . . .
C2 C 0.42580(17) 0.3571(6) 0.3728(2) 0.0179(6) Uani 1 1 d . . .

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 0.01365(19) 0.01458(19) 0.01305(19) 0.00013(14) 0.00666(14) 0.00121(13)
Zn2 0.0133(3) 0.0181(3) 0.0175(3) 0.000 0.0084(2) 0.000
P1 0.0101(4) 0.0116(4) 0.0102(4) -0.0003(3) 0.0040(3) 0.0015(3)
O1 0.0212(11) 0.0139(11) 0.0136(10) 0.0035(9) 0.0074(9) 0.0032(8)
O2 0.0115(10) 0.0160(11) 0.0170(11) -0.0027(9) 0.0017(9) 0.0008(8)
O3 0.0296(12) 0.0119(10) 0.0147(11) -0.0005(9) 0.0047(10) 0.0003(9)
O4 0.0126(11) 0.0358(13) 0.0133(11) -0.0029(10) 0.0058(9) 0.0064(9)
N1 0.0148(13) 0.0189(13) 0.0160(13) 0.0047(11) 0.0096(11) 0.0046(10)
N2 0.0262(15) 0.0200(14) 0.0186(14) 0.0085(11) 0.0136(12) 0.0087(11)
N3 0.0233(14) 0.0227(15) 0.0207(14) 0.0094(12) 0.0155(12) 0.0095(11)
N4 0.0323(16) 0.0233(15) 0.0271(16) 0.0074(13) 0.0153(14) 0.0143(12)
N5 0.0303(16) 0.0356(17) 0.0379(18) 0.0199(14) 0.0253(14) 0.0185(13)
C1 0.0184(15) 0.0171(15) 0.0148(16) 0.0008(12) 0.0071(13) 0.0009(12)
C2 0.0157(15) 0.0205(16) 0.0192(16) 0.0046(13) 0.0089(13) 0.0026(12)

_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 O3 1.903(2) 1_565 ?
Zn1 O4 1.942(2) 7_556 ?
Zn1 O1 1.953(2) . ?
Zn1 N1 2.039(2) . ?
Zn2 O2 1.955(2) 6 ?
Zn2 O2 1.955(2) 5_656 ?
Zn2 N3 1.980(2) 2_655 ?
Zn2 N3 1.981(2) . ?
P1 O3 1.515(2) . ?
P1 O4 1.5311(19) . ?
P1 O1 1.540(2) . ?
P1 O2 1.546(2) . ?
O2 Zn2 1.955(2) 5_656 ?
O3 Zn1 1.903(2) 1_545 ?
O4 Zn1 1.942(2) 7_556 ?
N1 C1 1.345(4) . ?
N1 C2 1.355(4) . ?
N2 C1 1.322(4) . ?
N2 N3 1.381(4) . ?
N2 H1 0.9481 . ?
N3 C2 1.314(4) . ?
N4 C1 1.339(4) . ?
N4 H2 0.9410 . ?
N4 H3 0.8757 . ?
N5 C2 1.342(4) . ?
N5 H4 0.8625 . ?
N5 H5 0.9331 . ?

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
O3 Zn1 O4 115.27(9) 1_565 7_556 ?
O3 Zn1 O1 111.75(9) 1_565 . ?
O4 Zn1 O1 112.36(9) 7_556 . ?
O3 Zn1 N1 113.46(10) 1_565 . ?
O4 Zn1 N1 100.79(9) 7_556 . ?
O1 Zn1 N1 101.97(9) . . ?
O2 Zn2 O2 102.11(12) 6 5_656 ?
O2 Zn2 N3 109.45(9) 6 2_655 ?
O2 Zn2 N3 110.29(10) 5_656 2_655 ?
O2 Zn2 N3 110.29(10) 6 . ?
O2 Zn2 N3 109.45(9) 5_656 . ?
N3 Zn2 N3 114.53(15) 2_655 . ?
O3 P1 O4 111.76(12) . . ?
O3 P1 O1 110.42(11) . . ?
O4 P1 O1 109.90(12) . . ?
O3 P1 O2 107.81(12) . . ?
O4 P1 O2 107.30(12) . . ?
O1 P1 O2 109.55(12) . . ?
P1 O1 Zn1 127.81(12) . . ?
P1 O2 Zn2 123.65(12) . 5_656 ?
P1 O3 Zn1 131.28(13) . 1_545 ?
P1 O4 Zn1 125.87(13) . 7_556 ?
C1 N1 C2 103.6(2) . . ?
C1 N1 Zn1 130.27(19) . . ?
C2 N1 Zn1 125.6(2) . . ?
C1 N2 N3 109.0(2) . . ?
C1 N2 H1 124.2 . . ?
N3 N2 H1 126.8 . . ?
C2 N3 N2 103.7(2) . . ?
C2 N3 Zn2 127.0(2) . . ?
N2 N3 Zn2 127.42(19) . . ?
C1 N4 H2 117.7 . . ?
C1 N4 H3 121.7 . . ?
H2 N4 H3 120.4 . . ?
C2 N5 H4 113.5 . . ?
C2 N5 H5 111.2 . . ?
H4 N5 H5 123.9 . . ?
N2 C1 N4 125.0(3) . . ?
N2 C1 N1 110.1(3) . . ?
N4 C1 N1 124.8(3) . . ?
N3 C2 N5 123.7(3) . . ?
N3 C2 N1 113.6(3) . . ?
N5 C2 N1 122.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.104
