# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'M Schroder'
_publ_contact_author_email       M.SCHRODER@NOTTINGHAM.AC.UK

_publ_section_title              
;
In Situ Synthesis of 5-Substituted-tetrazoles and
Metallosupramolecular Co-ordination Polymers
;
loop_
_publ_author_name
'M Schroder'
'Alexander Blake'
'Neil Champness'
'P Hubberstey'
'Xiang Lin.'
;
C.Wilson
;
'Wenbin Yang.'

# Attachment 'WYCrystEngComm.CIF'

data_(1)
_database_code_depnum_ccdc_archive 'CCDC 688599'
# zncnpo

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N5 O4 P Zn'
_chemical_formula_sum            'C6 H6 N5 O4 P Zn'
_chemical_formula_weight         308.50

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   5.4076(10)
_cell_length_b                   8.536(2)
_cell_length_c                   21.321(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.219(3)
_cell_angle_gamma                90.00
_cell_volume                     981.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3381
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Lath
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    2.678
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6284
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2358
_reflns_number_gt                2097
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer(Allen et al.,2004); PLATON(Spek,2003)'

_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)+(0.0249P)²+1.0947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'CH geometrically placed, HPO4 from delta-F'
_refine_ls_hydrogen_treatment    'riding model, HPO4 refined with restraints'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2206
_refine_ls_number_parameters     162
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0607
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.18242(4) 0.85791(3) 0.275739(11) 0.01072(8) Uani 1 1 d . . .
P1 P 0.69281(9) 1.04161(6) 0.29395(2) 0.00976(12) Uani 1 1 d . . .
O1 O 0.8431(3) 0.92675(18) 0.25663(7) 0.0131(3) Uani 1 1 d . . .
O2 O 0.7884(3) 1.20811(17) 0.29028(7) 0.0138(3) Uani 1 1 d . . .
O3 O 0.4184(3) 1.02725(17) 0.27390(7) 0.0130(3) Uani 1 1 d . . .
O4 O 0.7392(3) 1.00216(18) 0.36670(7) 0.0143(3) Uani 1 1 d D . .
N1 N 0.6834(4) 0.6759(2) 0.63731(9) 0.0177(4) Uani 1 1 d . . .
N2 N 0.1056(3) 0.6387(2) 0.44292(9) 0.0171(4) Uani 1 1 d . . .
N3 N 0.0458(4) 0.6703(2) 0.38271(9) 0.0182(4) Uani 1 1 d . . .
N4 N 0.2174(3) 0.7651(2) 0.36259(8) 0.0143(4) Uani 1 1 d . . .
N5 N 0.3928(3) 0.7968(2) 0.40884(8) 0.0139(4) Uani 1 1 d . . .
C2 C 0.7796(4) 0.7737(3) 0.59648(11) 0.0190(5) Uani 1 1 d . . .
H2A H 0.9263 0.8309 0.6084 0.023 Uiso 1 1 calc R . .
C3 C 0.6646(4) 0.7910(3) 0.53692(11) 0.0174(4) Uani 1 1 d . . .
H3A H 0.7317 0.8599 0.5076 0.021 Uiso 1 1 calc R . .
C4 C 0.4491(4) 0.7065(2) 0.52022(10) 0.0132(4) Uani 1 1 d . . .
C5 C 0.3559(4) 0.6048(3) 0.56440(10) 0.0153(4) Uani 1 1 d . . .
H5A H 0.2100 0.5455 0.5540 0.018 Uiso 1 1 calc R . .
C6 C 0.4780(4) 0.5919(3) 0.62288(10) 0.0165(4) Uani 1 1 d . . .
H6A H 0.4167 0.5233 0.6532 0.020 Uiso 1 1 calc R . .
C7 C 0.3184(4) 0.7167(2) 0.45787(10) 0.0126(4) Uani 1 1 d . . .
H1 H 0.741(6) 0.661(3) 0.6725(15) 0.030(8) Uiso 1 1 d . . .
H4 H 0.646(5) 0.935(3) 0.3801(14) 0.037(9) Uiso 1 1 d 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 0.00958(13) 0.01247(13) 0.00998(13) -0.00013(9) -0.00008(8) 0.00032(8)
P1 0.0091(3) 0.0102(2) 0.0100(3) -0.00002(18) 0.00063(18) -0.00057(18)
O1 0.0089(7) 0.0171(7) 0.0132(7) -0.0032(6) -0.0003(5) 0.0028(6)
O2 0.0160(7) 0.0125(7) 0.0130(7) 0.0018(6) 0.0009(6) -0.0026(6)
O3 0.0088(7) 0.0137(7) 0.0164(7) -0.0001(6) -0.0002(5) -0.0005(5)
O4 0.0141(8) 0.0163(8) 0.0125(7) 0.0026(6) 0.0010(6) -0.0045(6)
N1 0.0176(10) 0.0236(10) 0.0114(9) -0.0024(8) -0.0024(7) 0.0063(7)
N2 0.0149(9) 0.0216(10) 0.0143(9) 0.0025(7) -0.0016(7) -0.0044(7)
N3 0.0177(10) 0.0227(10) 0.0140(9) 0.0029(7) -0.0005(7) -0.0045(7)
N4 0.0132(9) 0.0167(9) 0.0127(9) 0.0006(7) -0.0006(6) -0.0015(7)
N5 0.0144(9) 0.0152(9) 0.0121(9) 0.0008(7) -0.0003(7) -0.0015(7)
C2 0.0144(11) 0.0222(12) 0.0201(11) -0.0049(9) -0.0010(8) -0.0006(9)
C3 0.0167(11) 0.0192(11) 0.0164(11) 0.0000(8) 0.0016(8) -0.0032(8)
C4 0.0126(10) 0.0146(10) 0.0123(10) -0.0011(8) 0.0000(7) 0.0014(8)
C5 0.0151(10) 0.0166(10) 0.0143(10) -0.0003(8) 0.0023(8) -0.0008(8)
C6 0.0204(11) 0.0168(10) 0.0127(10) 0.0016(8) 0.0038(8) 0.0041(8)
C7 0.0119(10) 0.0124(10) 0.0133(10) -0.0003(8) 0.0008(7) -0.0011(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9412(14) 1_455 ?
Zn1 O2 1.9168(15) 2_645 ?
Zn1 O3 1.9304(15) . ?
Zn1 N4 2.0102(18) . ?
P1 O2 1.5163(15) . ?
P1 O3 1.5188(15) . ?
P1 O1 1.5330(15) . ?
P1 O4 1.5891(16) . ?
N1 C2 1.339(3) . ?
N1 C6 1.339(3) . ?
N2 N3 1.328(3) . ?
N2 C7 1.347(3) . ?
N3 N4 1.326(3) . ?
N4 N5 1.344(2) . ?
N5 C7 1.336(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.394(3) . ?
C4 C5 1.402(3) . ?
C4 C7 1.461(3) . ?
C5 C6 1.372(3) . ?

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 113.23(6) 2_645 . ?
O2 Zn1 O1 100.10(6) 2_645 1_455 ?
O3 Zn1 O1 112.65(6) . 1_455 ?
O2 Zn1 N4 113.98(7) 2_645 . ?
O3 Zn1 N4 107.23(7) . . ?
O1 Zn1 N4 109.64(7) 1_455 . ?
O2 P1 O3 113.01(9) . . ?
O2 P1 O1 112.15(9) . . ?
O3 P1 O1 110.28(8) . . ?
O2 P1 O4 102.65(8) . . ?
O3 P1 O4 109.78(8) . . ?
O1 P1 O4 108.63(8) . . ?
P1 O1 Zn1 127.86(9) . 1_655 ?
P1 O2 Zn1 135.23(9) . 2_655 ?
P1 O3 Zn1 133.50(9) . . ?
C2 N1 C6 122.7(2) . . ?
N3 N2 C7 105.75(17) . . ?
N4 N3 N2 108.06(17) . . ?
N3 N4 N5 110.99(17) . . ?
N3 N4 Zn1 121.18(14) . . ?
N5 N4 Zn1 127.58(14) . . ?
C7 N5 N4 103.54(17) . . ?
N1 C2 C3 119.6(2) . . ?
C2 C3 C4 119.4(2) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C7 122.73(19) . . ?
C5 C4 C7 118.32(19) . . ?
C6 C5 C4 119.2(2) . . ?
N1 C6 C5 120.1(2) . . ?
N5 C7 N2 111.66(19) . . ?
N5 C7 C4 126.08(19) . . ?
N2 C7 C4 122.23(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 O1 Zn1 69.39(13) . . . 1_655 ?
O3 P1 O1 Zn1 -163.71(10) . . . 1_655 ?
O4 P1 O1 Zn1 -43.36(13) . . . 1_655 ?
O3 P1 O2 Zn1 -62.56(15) . . . 2_655 ?
O1 P1 O2 Zn1 62.86(15) . . . 2_655 ?
O4 P1 O2 Zn1 179.28(12) . . . 2_655 ?
O2 P1 O3 Zn1 -172.65(11) . . . . ?
O1 P1 O3 Zn1 60.93(14) . . . . ?
O4 P1 O3 Zn1 -58.73(14) . . . . ?
O2 Zn1 O3 P1 -77.66(14) 2_645 . . . ?
O1 Zn1 O3 P1 169.65(11) 1_455 . . . ?
N4 Zn1 O3 P1 48.93(14) . . . . ?
C7 N2 N3 N4 -0.4(2) . . . . ?
N2 N3 N4 N5 0.3(2) . . . . ?
N2 N3 N4 Zn1 -174.43(14) . . . . ?
O2 Zn1 N4 N3 -68.80(18) 2_645 . . . ?
O3 Zn1 N4 N3 165.06(16) . . . . ?
O1 Zn1 N4 N3 42.46(18) 1_455 . . . ?
O2 Zn1 N4 N5 117.41(17) 2_645 . . . ?
O3 Zn1 N4 N5 -8.73(19) . . . . ?
O1 Zn1 N4 N5 -131.33(17) 1_455 . . . ?
N3 N4 N5 C7 -0.1(2) . . . . ?
Zn1 N4 N5 C7 174.21(14) . . . . ?
C6 N1 C2 C3 0.3(3) . . . . ?
N1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 C7 -179.1(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C7 C4 C5 C6 179.1(2) . . . . ?
C2 N1 C6 C5 -0.5(3) . . . . ?
C4 C5 C6 N1 0.1(3) . . . . ?
N4 N5 C7 N2 -0.1(2) . . . . ?
N4 N5 C7 C4 177.8(2) . . . . ?
N3 N2 C7 N5 0.3(2) . . . . ?
N3 N2 C7 C4 -177.72(19) . . . . ?
C3 C4 C7 N5 4.6(3) . . . . ?
C5 C4 C7 N5 -174.0(2) . . . . ?
C3 C4 C7 N2 -177.7(2) . . . . ?
C5 C4 C7 N2 3.8(3) . . . . ?

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 H1 O1 0.80(3) 1.98(3) 2.768(3) 166(3) 4_576
O4 H4 N5 0.83(3) 1.94(3) 2.763(2) 172(3) .
C2 H2A O4 0.95 2.33 3.278(3) 173 3_776
C5 H5A N2 0.95 2.33 3.243(3) 162 3_566

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.985

_refine_diff_density_max         0.45
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.08

#===END of CIF

data_(2)
_database_code_depnum_ccdc_archive 'CCDC 688600'
# CDCNPO

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 Cd N10 O10 P2'
_chemical_formula_sum            'C12 H18 Cd N10 O10 P2'
_chemical_formula_weight         636.70

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'
Cd Cd -0.8075 1.2024 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9577(5)
_cell_length_b                   9.1474(7)
_cell_length_c                   9.4756(7)
_cell_angle_alpha                100.334(2)
_cell_angle_beta                 105.472(2)
_cell_angle_gamma                107.665(2)
_cell_volume                     531.09(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2845
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             318
_exptl_absorpt_coefficient_mu    1.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3282
_diffrn_reflns_av_R_equivalents  0.010
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2140
_reflns_number_gt                2093
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_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)+(0.0268P)²+0.3448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   
'CH geometrically placed; H2PO4 and H2O from delta-F'
_refine_ls_hydrogen_treatment    
'riding model; H2PO4 and H2O refined with restraints'
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.068(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2134
_refine_ls_number_parameters     181
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_ref         0.0458
_refine_ls_wR_factor_gt          0.0456
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_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
Cd1 Cd 0.0000 0.5000 0.0000 0.01038(8) Uani 1 2 d S . .
P1 P -0.37535(6) 0.25038(5) 0.11053(4) 0.01001(10) Uani 1 1 d . . .
O1 O -0.29969(19) 0.39597(15) 0.05876(14) 0.0157(2) Uani 1 1 d . . .
O2 O -0.25384(18) 0.13918(14) 0.10780(13) 0.0145(2) Uani 1 1 d . . .
O3 O -0.62059(19) 0.15687(15) 0.01590(15) 0.0179(3) Uani 1 1 d D . .
O4 O -0.3681(2) 0.31319(15) 0.27950(14) 0.0190(3) Uani 1 1 d D . .
O9 O -0.13000(19) 0.67618(15) -0.10372(14) 0.0147(2) Uani 1 1 d D . .
N1 N 0.3025(2) 1.36955(19) 0.61478(17) 0.0164(3) Uani 1 1 d . . .
N2 N 0.1526(2) 0.83866(17) 0.25831(16) 0.0140(3) Uani 1 1 d . . .
N3 N 0.1412(2) 0.68734(17) 0.23898(15) 0.0138(3) Uani 1 1 d . . .
N4 N 0.1954(2) 0.65567(17) 0.37177(15) 0.0147(3) Uani 1 1 d . . .
N5 N 0.2436(2) 0.78877(17) 0.48218(15) 0.0136(3) Uani 1 1 d . . .
C1 C 0.2402(3) 1.3176(2) 0.4620(2) 0.0180(3) Uani 1 1 d . . .
H1A H 0.2158 1.3870 0.4018 0.022 Uiso 1 1 calc R . .
C2 C 0.2121(3) 1.1634(2) 0.39351(19) 0.0159(3) Uani 1 1 d . . .
H2A H 0.1685 1.1253 0.2855 0.019 Uiso 1 1 calc R . .
C3 C 0.2483(3) 1.06314(19) 0.48425(18) 0.0120(3) Uani 1 1 d . . .
C4 C 0.3123(3) 1.1215(2) 0.64238(18) 0.0144(3) Uani 1 1 d . . .
H4A H 0.3365 1.0545 0.7056 0.017 Uiso 1 1 calc R . .
C5 C 0.3400(3) 1.2774(2) 0.70608(19) 0.0169(3) Uani 1 1 d . . .
H5A H 0.3853 1.3194 0.8138 0.020 Uiso 1 1 calc R . .
C6 C 0.2160(3) 0.8979(2) 0.40986(18) 0.0113(3) Uani 1 1 d . . .
H9B H -0.193(4) 0.728(3) -0.062(3) 0.031(7) Uiso 1 1 d D . .
H9A H -0.018(3) 0.746(3) -0.105(3) 0.037(7) Uiso 1 1 d D . .
H1 H 0.321(4) 1.457(3) 0.644(3) 0.028(7) Uiso 1 1 d . . .
H3 H -0.653(5) 0.0574(14) -0.019(4) 0.064(10) Uiso 1 1 d D . .
H4 H -0.328(5) 0.264(3) 0.342(3) 0.057(9) Uiso 1 1 d 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
Cd1 0.01342(10) 0.00862(11) 0.00917(10) 0.00215(6) 0.00382(6) 0.00444(6)
P1 0.01197(19) 0.0080(2) 0.01012(19) 0.00181(14) 0.00380(15) 0.00420(15)
O1 0.0171(6) 0.0144(6) 0.0200(6) 0.0088(5) 0.0087(5) 0.0075(5)
O2 0.0139(5) 0.0101(6) 0.0184(6) 0.0017(4) 0.0039(5) 0.0056(4)
O3 0.0126(6) 0.0101(6) 0.0264(6) -0.0014(5) 0.0030(5) 0.0048(5)
O4 0.0357(7) 0.0147(6) 0.0118(5) 0.0050(5) 0.0087(5) 0.0151(5)
O9 0.0156(6) 0.0142(6) 0.0178(6) 0.0061(5) 0.0068(5) 0.0085(5)
N1 0.0205(7) 0.0088(8) 0.0187(7) 0.0006(6) 0.0055(6) 0.0068(6)
N2 0.0184(7) 0.0109(7) 0.0121(6) 0.0022(5) 0.0037(5) 0.0067(5)
N3 0.0179(7) 0.0111(7) 0.0122(6) 0.0027(5) 0.0044(5) 0.0063(5)
N4 0.0207(7) 0.0111(7) 0.0115(6) 0.0021(5) 0.0046(5) 0.0061(5)
N5 0.0192(7) 0.0102(7) 0.0119(6) 0.0025(5) 0.0048(5) 0.0069(5)
C1 0.0224(9) 0.0148(9) 0.0185(8) 0.0067(6) 0.0058(7) 0.0091(7)
C2 0.0217(8) 0.0148(9) 0.0131(7) 0.0045(6) 0.0054(7) 0.0094(6)
C3 0.0118(7) 0.0102(8) 0.0140(7) 0.0022(6) 0.0039(6) 0.0052(6)
C4 0.0187(8) 0.0125(8) 0.0125(7) 0.0044(6) 0.0047(6) 0.0066(6)
C5 0.0202(8) 0.0150(9) 0.0140(7) 0.0015(6) 0.0044(6) 0.0073(6)
C6 0.0133(7) 0.0101(8) 0.0117(7) 0.0035(6) 0.0050(6) 0.0051(6)

_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
Cd1 O1 2.2735(12) . ?
Cd1 N3 2.3300(14) . ?
Cd1 O9 2.3151(12) . ?
P1 O1 1.4960(13) . ?
P1 O2 1.5082(13) . ?
P1 O3 1.5716(12) . ?
P1 O4 1.5828(12) . ?
N1 C1 1.342(2) . ?
N1 C5 1.342(2) . ?
N2 C6 1.337(2) . ?
N2 N3 1.338(2) . ?
N3 N4 1.324(2) . ?
N4 N5 1.3406(19) . ?
N5 C6 1.340(2) . ?
C1 C2 1.373(3) . ?
C2 C3 1.397(2) . ?
C3 C4 1.393(2) . ?
C3 C6 1.469(2) . ?
C4 C5 1.378(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cd1 N3 86.99(5) . . ?
O1 Cd1 O9 91.93(4) . . ?
O9 Cd1 N3 89.06(5) . . ?
O1 P1 O2 117.60(7) . . ?
O1 P1 O3 108.08(7) . . ?
O2 P1 O3 110.59(7) . . ?
O1 P1 O4 106.09(7) . . ?
O2 P1 O4 109.10(7) . . ?
O3 P1 O4 104.52(7) . . ?
P1 O1 Cd1 130.55(7) . . ?
C5 N1 C1 123.03(16) . . ?
C6 N2 N3 103.69(14) . . ?
N4 N3 N2 111.17(13) . . ?
N4 N3 Cd1 125.39(11) . . ?
N2 N3 Cd1 122.96(10) . . ?
N3 N4 N5 107.78(13) . . ?
C6 N5 N4 105.52(13) . . ?
N1 C1 C2 119.55(17) . . ?
C1 C2 C3 119.29(15) . . ?
C4 C3 C2 119.42(16) . . ?
C4 C3 C6 121.67(15) . . ?
C2 C3 C6 118.91(14) . . ?
C5 C4 C3 119.22(16) . . ?
N1 C5 C4 119.48(16) . . ?
N2 C6 N5 111.84(15) . . ?
N2 C6 C3 122.79(15) . . ?
N5 C6 C3 125.37(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 N4 -0.14(18) . . . . ?
N2 N3 N4 N5 0.10(18) . . . . ?
N3 N4 N5 C6 -0.01(18) . . . . ?
C5 N1 C1 C2 0.2(3) . . . . ?
N1 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C6 179.50(16) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C6 C3 C4 C5 -179.97(15) . . . . ?
C1 N1 C5 C4 -0.7(3) . . . . ?
C3 C4 C5 N1 0.8(3) . . . . ?
N3 N2 C6 N5 0.14(19) . . . . ?
N3 N2 C6 C3 -179.38(14) . . . . ?
N4 N5 C6 N2 -0.08(19) . . . . ?
N4 N5 C6 C3 179.43(15) . . . . ?
C4 C3 C6 N2 179.30(16) . . . . ?
C2 C3 C6 N2 -0.2(2) . . . . ?
C4 C3 C6 N5 -0.2(3) . . . . ?
C2 C3 C6 N5 -179.68(16) . . . . ?

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
O9 H9B O3 0.85(3) 1.99(3) 2.8212(18) 166(2) 2_465
O9 H9A O2 0.85(3) 1.87(3) 2.7069(17) 166(3) 2_565
N1 H1 O4 0.76(3) 1.99(3) 2.746(2) 180(3) 2_576
O3 H3 O2 0.85(3) 1.68(3) 2.5199(17) 172(3) 2_455
O4 H4 N5 0.85(3) 1.81(3) 2.6309(19) 162(3) 2_566
O4 H4 N4 0.85(3) 2.51(3) 3.1273(18) 131(3) 2_566

_diffrn_measured_fraction_theta_max 0.879
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.923

_refine_diff_density_max         0.37
_refine_diff_density_min         -0.41
_refine_diff_density_rms         0.07

#===END of CIF

data_(3)
_database_code_depnum_ccdc_archive 'CCDC 688601'
# ZNCNPY

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N10 O4 Zn, 2(H2 O)'
_chemical_formula_sum            'C12 H20 N10 O6 Zn'
_chemical_formula_weight         465.75

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1480(12)
_cell_length_b                   7.7330(13)
_cell_length_c                   8.6938(15)
_cell_angle_alpha                88.434(3)
_cell_angle_beta                 89.527(3)
_cell_angle_gamma                80.241(2)
_cell_volume                     473.4(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3044
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Bruker SADABS v2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4258
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2107
_reflns_number_gt                2069
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_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)+(0.0320P)²+0.2055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'CH geometrically placed, H2O from delta-F'
_refine_ls_hydrogen_treatment    'riding model, H2O refined with restraints'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2104
_refine_ls_number_parameters     157
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_restrained_S_all      1.12
_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 0.5000 0.5000 0.5000 0.01452(9) Uani 1 2 d S . .
O1 O 0.33126(16) 0.66067(14) 0.33634(13) 0.0188(2) Uani 1 1 d D . .
H1B H 0.2238(18) 0.636(3) 0.325(3) 0.035(6) Uiso 1 1 d D . .
H1C H 0.328(3) 0.7629(16) 0.304(2) 0.033(6) Uiso 1 1 d D . .
O2 O 0.28549(16) 0.34194(15) 0.52538(13) 0.0218(2) Uani 1 1 d D . .
H2B H 0.254(3) 0.283(3) 0.455(2) 0.039(6) Uiso 1 1 d D . .
H2C H 0.198(2) 0.361(3) 0.589(2) 0.032(6) Uiso 1 1 d D . .
O3 O 0.01884(16) 0.39954(14) 0.75239(12) 0.0192(2) Uani 1 1 d D . .
H3B H 0.055(3) 0.343(3) 0.8326(17) 0.032(6) Uiso 1 1 d D . .
H3C H -0.017(3) 0.5015(16) 0.779(3) 0.039(6) Uiso 1 1 d D . .
N1 N 0.61964(18) 0.33014(16) 0.32285(14) 0.0165(2) Uani 1 1 d . . .
N2 N 0.83828(19) -0.19937(17) -0.01626(15) 0.0199(3) Uani 1 1 d . . .
N3 N 0.85379(19) -0.26707(17) -0.15670(15) 0.0216(3) Uani 1 1 d . . .
N4 N 0.79388(19) -0.14428(17) -0.26061(15) 0.0211(3) Uani 1 1 d . . .
N5 N 0.73714(19) 0.00898(17) -0.19055(15) 0.0192(3) Uani 1 1 d . . .
C1 C 0.6639(3) 0.1559(2) 0.34976(18) 0.0235(3) Uani 1 1 d . . .
H1A H 0.6602 0.1138 0.4508 0.028 Uiso 1 1 calc R . .
C2 C 0.7143(2) 0.0366(2) 0.23553(18) 0.0228(3) Uani 1 1 d . . .
H2A H 0.7435 -0.0828 0.2600 0.027 Uiso 1 1 calc R . .
C3 C 0.7213(2) 0.09574(19) 0.08379(16) 0.0156(3) Uani 1 1 d . . .
C4 C 0.6815(2) 0.2768(2) 0.05570(17) 0.0184(3) Uani 1 1 d . . .
H4A H 0.6888 0.3225 -0.0438 0.022 Uiso 1 1 calc R . .
C5 C 0.6313(2) 0.38750(19) 0.17657(17) 0.0176(3) Uani 1 1 d . . .
H5A H 0.6043 0.5077 0.1556 0.021 Uiso 1 1 calc R . .
C6 C 0.7663(2) -0.02953(19) -0.04060(17) 0.0161(3) 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 0.01965(13) 0.01318(13) 0.01008(12) -0.00289(8) 0.00091(9) -0.00056(8)
O1 0.0223(5) 0.0164(5) 0.0171(5) 0.0008(4) -0.0029(4) -0.0015(4)
O2 0.0258(6) 0.0248(6) 0.0166(5) -0.0082(4) 0.0056(5) -0.0089(4)
O3 0.0235(5) 0.0166(5) 0.0164(5) -0.0028(4) 0.0011(4) -0.0002(4)
N1 0.0196(6) 0.0162(6) 0.0130(6) -0.0021(5) 0.0003(5) -0.0010(4)
N2 0.0251(6) 0.0177(6) 0.0157(6) -0.0058(5) -0.0011(5) 0.0004(5)
N3 0.0274(7) 0.0190(6) 0.0172(6) -0.0066(5) -0.0012(5) 0.0001(5)
N4 0.0277(7) 0.0186(6) 0.0165(6) -0.0069(5) -0.0009(5) -0.0011(5)
N5 0.0258(7) 0.0169(6) 0.0143(6) -0.0049(5) -0.0005(5) -0.0009(5)
C1 0.0373(9) 0.0179(7) 0.0136(7) -0.0004(6) 0.0013(6) -0.0003(6)
C2 0.0355(9) 0.0141(7) 0.0171(7) -0.0007(6) 0.0019(6) 0.0001(6)
C3 0.0159(6) 0.0164(7) 0.0142(7) -0.0040(5) 0.0002(5) -0.0014(5)
C4 0.0238(7) 0.0188(7) 0.0120(6) -0.0012(5) 0.0011(6) -0.0014(5)
C5 0.0211(7) 0.0146(7) 0.0164(7) -0.0008(5) 0.0011(6) -0.0009(5)
C6 0.0168(6) 0.0168(7) 0.0147(7) -0.0039(5) 0.0005(5) -0.0024(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.1087(11) . ?
Zn1 O2 2.1234(11) . ?
Zn1 N1 2.1299(12) . ?
N1 C5 1.3421(19) . ?
N1 C1 1.345(2) . ?
N2 N3 1.3380(18) . ?
N2 C6 1.3387(19) . ?
N3 N4 1.3125(19) . ?
N4 N5 1.3464(17) . ?
N5 C6 1.3394(19) . ?
C1 C2 1.378(2) . ?
C2 C3 1.388(2) . ?
C3 C4 1.396(2) . ?
C3 C6 1.4687(19) . ?
C4 C5 1.380(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O2 89.81(5) . . ?
O1 Zn1 N1 90.25(5) . . ?
O2 Zn1 N1 87.68(5) . . ?
C5 N1 C1 116.92(13) . . ?
C5 N1 Zn1 121.89(10) . . ?
C1 N1 Zn1 120.64(10) . . ?
N3 N2 C6 104.61(12) . . ?
N4 N3 N2 109.94(12) . . ?
N3 N4 N5 109.33(12) . . ?
C6 N5 N4 104.54(12) . . ?
N1 C1 C2 123.46(14) . . ?
C1 C2 C3 119.52(14) . . ?
C2 C3 C4 117.29(13) . . ?
C2 C3 C6 120.47(13) . . ?
C4 C3 C6 122.24(13) . . ?
C5 C4 C3 119.57(14) . . ?
N1 C5 C4 123.18(14) . . ?
N2 C6 N5 111.57(13) . . ?
N2 C6 C3 123.39(13) . . ?
N5 C6 C3 125.02(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 N4 -0.08(17) . . . . ?
N2 N3 N4 N5 0.10(18) . . . . ?
N3 N4 N5 C6 -0.08(17) . . . . ?
C5 N1 C1 C2 -1.8(2) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C1 C2 C3 C6 -177.22(15) . . . . ?
C2 C3 C4 C5 -2.2(2) . . . . ?
C6 C3 C4 C5 176.91(14) . . . . ?
C1 N1 C5 C4 1.5(2) . . . . ?
C3 C4 C5 N1 0.5(2) . . . . ?
N3 N2 C6 N5 0.04(17) . . . . ?
N3 N2 C6 C3 178.57(13) . . . . ?
N4 N5 C6 N2 0.02(17) . . . . ?
N4 N5 C6 C3 -178.48(14) . . . . ?
C2 C3 C6 N2 -13.6(2) . . . . ?
C4 C3 C6 N2 167.34(14) . . . . ?
C2 C3 C6 N5 164.78(15) . . . . ?
C4 C3 C6 N5 -14.3(2) . . . . ?

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
O1 H1B O3 0.830(10) 1.930(11) 2.7424(16) 166(2) 2_566
O1 H1C N5 0.830(10) 1.982(11) 2.7895(18) 164(2) 2_665
O2 H2B N4 0.827(10) 2.089(10) 2.9094(17) 172(2) 2_655
O2 H2C O3 0.827(10) 1.901(10) 2.7248(16) 174(2) .
O3 H3B N2 0.832(10) 2.000(10) 2.8303(18) 175(2) 2_656
O3 H3C N3 0.826(10) 1.963(11) 2.7799(17) 170(2) 1_466

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.966

_refine_diff_density_max         0.42
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.06

#===END of CIF

data_(4)
_database_code_depnum_ccdc_archive 'CCDC 688602'
# CNPOZN

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N10 O6 Zn'
_chemical_formula_sum            'C12 H16 N10 O6 Zn'
_chemical_formula_weight         461.72

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                   21.546(6)
_cell_length_b                   6.928(2)
_cell_length_c                   11.201(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.737(5)
_cell_angle_gamma                90.00
_cell_volume                     1663.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2187
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    1.539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5168
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.56
_reflns_number_total             2077
_reflns_number_gt                1746
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek, 2003)'

_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)+(0.0509P)²+1.4883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'CH geometrically placed, H2O from delta-F'
_refine_ls_hydrogen_treatment    'riding model, H2O refined with restraints'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1920
_refine_ls_number_parameters     148
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_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 0.5000 0.16455(4) 0.2500 0.01294(12) Uani 1 2 d S . .
O1 O 0.06262(6) 0.16310(18) 0.09806(13) 0.0172(3) Uani 1 1 d . . .
O2 O 0.47459(6) -0.0596(2) 0.12619(12) 0.0172(3) Uani 1 1 d D . .
O3 O 0.47316(7) 0.3949(2) 0.13470(12) 0.0177(3) Uani 1 1 d D . .
N1 N 0.12209(7) 0.1567(2) 0.14514(15) 0.0137(3) Uani 1 1 d . . .
N2 N 0.32968(8) 0.1195(2) 0.40828(14) 0.0170(3) Uani 1 1 d . . .
N3 N 0.39169(8) 0.1248(2) 0.41376(14) 0.0170(3) Uani 1 1 d . . .
N4 N 0.40832(8) 0.1551(2) 0.30408(15) 0.0155(3) Uani 1 1 d . . .
N5 N 0.35767(8) 0.1690(2) 0.22457(15) 0.0161(3) Uani 1 1 d . . .
C1 C 0.16741(9) 0.1257(3) 0.07224(17) 0.0165(4) Uani 1 1 d . . .
H1A H 0.1569 0.1094 -0.0115 0.020 Uiso 1 1 calc R . .
C2 C 0.22885(9) 0.1177(3) 0.11931(17) 0.0156(4) Uani 1 1 d . . .
H2A H 0.2605 0.0918 0.0682 0.019 Uiso 1 1 calc R . .
C3 C 0.24489(9) 0.1474(3) 0.24155(17) 0.0130(4) Uani 1 1 d . . .
C4 C 0.19687(9) 0.1805(3) 0.31398(17) 0.0153(4) Uani 1 1 d . . .
H4A H 0.2063 0.2008 0.3977 0.018 Uiso 1 1 calc R . .
C5 C 0.13585(9) 0.1837(3) 0.26375(17) 0.0156(4) Uani 1 1 d . . .
H5A H 0.1032 0.2052 0.3133 0.019 Uiso 1 1 calc R . .
C6 C 0.31032(9) 0.1458(2) 0.29200(17) 0.0132(4) Uani 1 1 d . . .
H2B H 0.5052(9) -0.132(3) 0.120(2) 0.028(7) Uiso 1 1 d D . .
H3C H 0.4595(12) 0.372(4) 0.0633(12) 0.032(7) Uiso 1 1 d D . .
H3B H 0.5026(9) 0.474(3) 0.133(2) 0.036(8) Uiso 1 1 d D . .
H2C H 0.4507(10) -0.058(4) 0.0626(15) 0.036(8) Uiso 1 1 d 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 0.01023(17) 0.01631(18) 0.01224(17) 0.000 0.00096(11) 0.000
O1 0.0100(6) 0.0204(7) 0.0203(7) -0.0007(5) -0.0031(5) 0.0000(5)
O2 0.0136(7) 0.0212(7) 0.0163(7) -0.0034(6) -0.0015(5) 0.0013(5)
O3 0.0164(7) 0.0203(7) 0.0156(7) 0.0021(6) -0.0014(5) -0.0029(5)
N1 0.0105(8) 0.0132(8) 0.0170(8) 0.0008(6) -0.0007(6) 0.0007(5)
N2 0.0127(8) 0.0229(8) 0.0153(8) 0.0007(6) 0.0013(6) 0.0004(6)
N3 0.0126(8) 0.0215(8) 0.0169(8) -0.0001(6) 0.0007(6) 0.0000(6)
N4 0.0135(8) 0.0191(8) 0.0135(7) 0.0003(6) -0.0008(6) 0.0001(6)
N5 0.0123(8) 0.0203(8) 0.0156(8) 0.0009(6) 0.0004(6) -0.0005(6)
C1 0.0173(10) 0.0193(9) 0.0126(8) -0.0015(7) 0.0006(7) 0.0010(7)
C2 0.0135(9) 0.0178(9) 0.0157(9) 0.0013(7) 0.0028(7) 0.0018(7)
C3 0.0115(9) 0.0117(8) 0.0154(9) 0.0012(6) -0.0003(7) 0.0004(6)
C4 0.0146(9) 0.0180(9) 0.0132(9) -0.0007(7) 0.0010(7) -0.0005(7)
C5 0.0148(9) 0.0170(9) 0.0153(9) -0.0003(7) 0.0039(7) -0.0002(7)
C6 0.0132(9) 0.0117(8) 0.0147(8) 0.0001(7) 0.0014(7) 0.0009(6)

_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 2.1170(14) . ?
Zn1 O3 2.0977(15) . ?
Zn1 N4 2.1242(17) . ?
O1 N1 1.337(2) . ?
N1 C5 1.345(3) . ?
N1 C1 1.351(2) . ?
N2 N3 1.332(2) . ?
N2 C6 1.340(3) . ?
N3 N4 1.330(2) . ?
N4 N5 1.341(2) . ?
N5 C6 1.339(2) . ?
C1 C2 1.376(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.396(3) . ?
C3 C6 1.466(3) . ?
C4 C5 1.378(3) . ?

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 O3 80.93(8) 2_655 . ?
O3 Zn1 O2 177.01(5) 2_655 . ?
O3 Zn1 O2 96.74(6) . . ?
O2 Zn1 O2 85.65(8) . 2_655 ?
O3 Zn1 N4 93.15(6) 2_655 . ?
O3 Zn1 N4 89.54(6) . . ?
O2 Zn1 N4 88.69(6) . . ?
O2 Zn1 N4 88.72(6) 2_655 . ?
N4 Zn1 N4 176.47(9) . 2_655 ?
O1 N1 C5 119.53(15) . . ?
O1 N1 C1 119.28(16) . . ?
C5 N1 C1 121.18(17) . . ?
N3 N2 C6 104.75(15) . . ?
N4 N3 N2 108.87(15) . . ?
N3 N4 N5 110.37(15) . . ?
N3 N4 Zn1 127.75(13) . . ?
N5 N4 Zn1 121.77(13) . . ?
C6 N5 N4 103.42(16) . . ?
N1 C1 C2 120.03(18) . . ?
C1 C2 C3 120.33(18) . . ?
C2 C3 C4 118.03(18) . . ?
C2 C3 C6 120.81(17) . . ?
C4 C3 C6 121.16(17) . . ?
C5 C4 C3 119.86(18) . . ?
N1 C5 C4 120.54(17) . . ?
N5 C6 N2 112.59(17) . . ?
N5 C6 C3 122.65(17) . . ?
N2 C6 C3 124.76(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 N4 0.6(2) . . . . ?
N2 N3 N4 N5 -0.4(2) . . . . ?
N3 N4 N5 C6 0.04(19) . . . . ?
O1 N1 C1 C2 -179.66(16) . . . . ?
C5 N1 C1 C2 1.2(3) . . . . ?
N1 C1 C2 C3 -2.0(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C6 -177.91(17) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C6 C3 C4 C5 179.16(17) . . . . ?
O1 N1 C5 C4 -179.07(16) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
N4 N5 C6 N2 0.3(2) . . . . ?
N4 N5 C6 C3 -179.06(16) . . . . ?
N3 N2 C6 N5 -0.6(2) . . . . ?
N3 N2 C6 C3 178.82(16) . . . . ?
C2 C3 C6 N5 18.7(3) . . . . ?
C4 C3 C6 N5 -160.69(18) . . . . ?
C2 C3 C6 N2 -160.62(19) . . . . ?
C4 C3 C6 N2 20.0(3) . . . . ?

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
O2 H2B O1 0.835(10) 1.917(11) 2.740(2) 168(3) 3_545
O3 H3C O1 0.839(10) 1.839(11) 2.674(2) 173(3) 7
O3 H3B O1 0.839(10) 1.909(11) 2.737(2) 169(3) 3
O2 H2C N3 0.836(10) 2.046(12) 2.865(2) 166(3) 6

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.994

_refine_diff_density_max         0.64
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.08

#===END of CIF

data_(5)
_database_code_depnum_ccdc_archive 'CCDC 688603'
# NIPNAZ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N10 Ni O6'
_chemical_formula_sum            'C12 H16 N10 Ni O6'
_chemical_formula_weight         455.06

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'
Ni Ni 0.3393 1.1124 '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                   21.403(3)
_cell_length_b                   6.9036(9)
_cell_length_c                   11.1612(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.837(2)
_cell_angle_gamma                90.00
_cell_volume                     1640.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3474
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.35

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale green'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    1.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS v2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7468
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2030
_reflns_number_gt                1673
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_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)+(0.0442P)²+2.1617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'CH geometrically placed, H2O from delta-F'
_refine_ls_hydrogen_treatment    'riding model, H2O refined with restraints'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1875
_refine_ls_number_parameters     148
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_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
Ni1 Ni 0.0000 0.66046(4) 0.2500 0.01606(12) Uani 1 2 d S . .
O1 O 0.43828(6) 0.66049(18) 0.40090(12) 0.0221(3) Uani 1 1 d . . .
O2 O -0.02600(6) 0.8861(2) 0.13514(12) 0.0209(3) Uani 1 1 d D . .
H2B H -0.0427(11) 0.862(3) 0.0656(12) 0.032(7) Uiso 1 1 d D . .
H2C H 0.0040(8) 0.963(3) 0.132(2) 0.031(6) Uiso 1 1 d D . .
O3 O 0.02518(6) 0.43983(19) 0.37103(11) 0.0202(3) Uani 1 1 d D . .
H3B H 0.0481(9) 0.445(4) 0.4359(13) 0.029(6) Uiso 1 1 d D . .
H3C H -0.0057(8) 0.368(3) 0.378(2) 0.030(7) Uiso 1 1 d D . .
N1 N 0.37834(7) 0.6545(2) 0.35466(14) 0.0183(3) Uani 1 1 d . . .
N2 N 0.16841(7) 0.6190(2) 0.09119(14) 0.0206(3) Uani 1 1 d . . .
N3 N 0.10620(8) 0.6248(2) 0.08708(14) 0.0209(3) Uani 1 1 d . . .
N4 N 0.09018(7) 0.6546(2) 0.19780(14) 0.0191(3) Uani 1 1 d . . .
N5 N 0.14063(7) 0.6678(2) 0.27629(14) 0.0194(3) Uani 1 1 d . . .
C2 C 0.33269(9) 0.6241(3) 0.42777(17) 0.0209(4) Uani 1 1 d . . .
H2A H 0.3432 0.6083 0.5101 0.025 Uiso 1 1 calc R . .
C3 C 0.27100(9) 0.6166(3) 0.38142(16) 0.0196(4) Uani 1 1 d . . .
H3A H 0.2400 0.5916 0.4320 0.024 Uiso 1 1 calc R . .
C4 C 0.25440(9) 0.6464(2) 0.25822(16) 0.0170(3) Uani 1 1 d . . .
C5 C 0.30282(9) 0.6786(2) 0.18539(16) 0.0190(4) Uani 1 1 d . . .
H5A H 0.2934 0.6985 0.1031 0.023 Uiso 1 1 calc R . .
C6 C 0.36418(9) 0.6810(3) 0.23494(17) 0.0205(4) Uani 1 1 d . . .
H6A H 0.3962 0.7009 0.1859 0.025 Uiso 1 1 calc R . .
C7 C 0.18846(9) 0.6449(2) 0.20880(16) 0.0173(3) 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
Ni1 0.01732(18) 0.01858(18) 0.01274(17) 0.000 0.00380(12) 0.000
O1 0.0182(6) 0.0249(7) 0.0226(7) 0.0004(5) -0.0007(5) 0.0006(5)
O2 0.0213(7) 0.0233(7) 0.0180(6) 0.0035(5) 0.0015(5) -0.0019(5)
O3 0.0197(7) 0.0239(7) 0.0167(6) 0.0029(5) 0.0004(5) -0.0013(5)
N1 0.0208(8) 0.0157(7) 0.0187(7) -0.0012(6) 0.0031(6) -0.0005(6)
N2 0.0199(8) 0.0243(8) 0.0181(7) -0.0008(6) 0.0045(6) 0.0001(6)
N3 0.0196(8) 0.0258(8) 0.0173(7) -0.0008(6) 0.0024(6) -0.0008(6)
N4 0.0195(8) 0.0205(8) 0.0176(7) -0.0005(6) 0.0038(6) 0.0000(6)
N5 0.0194(8) 0.0220(8) 0.0170(7) -0.0002(6) 0.0029(6) 0.0000(6)
C2 0.0248(9) 0.0233(9) 0.0149(8) 0.0012(7) 0.0034(7) -0.0002(7)
C3 0.0229(9) 0.0194(9) 0.0174(8) -0.0007(7) 0.0068(7) -0.0017(7)
C4 0.0204(9) 0.0131(7) 0.0177(8) -0.0013(6) 0.0031(7) 0.0013(6)
C5 0.0236(9) 0.0188(9) 0.0151(8) 0.0014(6) 0.0048(7) 0.0005(7)
C6 0.0230(9) 0.0213(9) 0.0181(9) 0.0008(7) 0.0066(7) 0.0006(7)
C7 0.0212(9) 0.0144(8) 0.0168(8) 0.0001(6) 0.0046(7) -0.0014(6)

_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
Ni1 O2 2.0580(14) . ?
Ni1 O3 2.0706(13) . ?
Ni1 N4 2.0725(16) . ?
O1 N1 1.334(2) . ?
N1 C2 1.351(2) . ?
N1 C6 1.352(2) . ?
N2 N3 1.328(2) . ?
N2 C7 1.351(2) . ?
N3 N4 1.332(2) . ?
N4 N5 1.323(2) . ?
N5 C7 1.341(2) . ?
C2 C3 1.369(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.398(3) . ?
C4 C7 1.462(3) . ?
C5 C6 1.372(3) . ?

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 Ni1 O2 81.59(8) 2 . ?
O2 Ni1 O3 96.58(6) 2 . ?
O2 Ni1 O3 177.79(5) . . ?
O3 Ni1 O3 85.28(8) 2 . ?
O2 Ni1 N4 89.40(6) 2 . ?
O2 Ni1 N4 92.31(6) . . ?
O3 Ni1 N4 89.44(6) 2 . ?
O3 Ni1 N4 88.90(6) . . ?
N4 Ni1 N4 177.74(8) 2 . ?
O1 N1 C2 119.81(15) . . ?
O1 N1 C6 119.23(15) . . ?
C2 N1 C6 120.96(17) . . ?
N3 N2 C7 104.35(15) . . ?
N2 N3 N4 108.94(15) . . ?
N5 N4 N3 110.82(15) . . ?
N5 N4 Ni1 122.23(12) . . ?
N3 N4 Ni1 126.80(13) . . ?
N4 N5 C7 103.78(15) . . ?
N1 C2 C3 120.42(17) . . ?
C2 C3 C4 120.28(17) . . ?
C5 C4 C3 117.72(17) . . ?
C5 C4 C7 121.71(17) . . ?
C3 C4 C7 120.56(17) . . ?
C6 C5 C4 120.20(17) . . ?
N1 C6 C5 120.38(17) . . ?
N5 C7 N2 112.11(17) . . ?
N5 C7 C4 123.37(17) . . ?
N2 C7 C4 124.52(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 N4 0.48(19) . . . . ?
N2 N3 N4 N5 -0.3(2) . . . . ?
N3 N4 N5 C7 0.02(18) . . . . ?
O1 N1 C2 C3 -179.63(16) . . . . ?
C6 N1 C2 C3 1.0(3) . . . . ?
N1 C2 C3 C4 -2.0(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C2 C3 C4 C7 -177.95(16) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C7 C4 C5 C6 179.34(16) . . . . ?
O1 N1 C6 C5 -178.95(15) . . . . ?
C2 N1 C6 C5 0.4(3) . . . . ?
C4 C5 C6 N1 -0.8(3) . . . . ?
N4 N5 C7 N2 0.29(19) . . . . ?
N4 N5 C7 C4 -179.19(16) . . . . ?
N3 N2 C7 N5 -0.5(2) . . . . ?
N3 N2 C7 C4 178.99(16) . . . . ?
C5 C4 C7 N5 -161.07(17) . . . . ?
C3 C4 C7 N5 18.4(3) . . . . ?
C5 C4 C7 N2 19.5(3) . . . . ?
C3 C4 C7 N2 -160.98(17) . . . . ?

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
O2 H2B O1 0.838(10) 1.848(12) 2.668(2) 165(3) 8_465
O2 H2C O1 0.838(10) 1.899(11) 2.726(2) 169(2) 4
O3 H3B N3 0.833(10) 2.050(12) 2.858(2) 164(2) 6_566
O3 H3C O1 0.836(10) 1.903(11) 2.723(2) 167(2) 3_445
C6 H6A O3 0.93 2.48 3.282(2) 144 4

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994

_refine_diff_density_max         0.66
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.07

#===END of CIF

data_(6)
_database_code_depnum_ccdc_archive 'CCDC 688604'
# Fetzcn

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N O2 +, N O3 -'
_chemical_formula_sum            'C6 H6 N2 O5'
_chemical_formula_weight         186.13

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   6.6590(8)
_cell_length_b                   8.1864(10)
_cell_length_c                   14.140(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.398(2)
_cell_angle_gamma                90.00
_cell_volume                     770.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1643
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.1

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4578
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         27.52
_reflns_number_total             1732
_reflns_number_gt                1238
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_refine_special_details          
;
?
;

_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)+(0.036P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   'O-H from delta-F; others geometrically placed'
_refine_ls_hydrogen_treatment    'rigid rotating group; riding model'
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0066(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1732
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_restrained_S_all      1.00
_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
N1 N 0.39621(17) 1.41664(14) 1.14896(8) 0.0384(3) Uani 1 1 d . . .
O1 O 0.05426(14) 1.19518(10) 0.86606(6) 0.0374(2) Uani 1 1 d . . .
O2 O 0.19432(14) 0.97470(10) 0.93411(6) 0.0333(2) Uani 1 1 d . . .
H2 H 0.148(2) 0.9256(19) 0.8830(11) 0.060(5) Uiso 1 1 d . . .
O3 O -0.03837(15) 0.68284(11) 0.67561(7) 0.0464(3) Uani 1 1 d . . .
O4 O 0.05307(16) 0.86522(10) 0.77595(6) 0.0458(3) Uani 1 1 d . . .
O5 O 0.10780(16) 0.61096(12) 0.80641(7) 0.0512(3) Uani 1 1 d . . .
C1 C 0.3036(2) 1.49059(17) 1.07636(9) 0.0380(3) Uani 1 1 d . . .
H1A H 0.2917 1.6062 1.0752 0.046 Uiso 1 1 calc R . .
C2 C 0.22615(19) 1.39909(15) 1.00387(9) 0.0320(3) Uani 1 1 d . . .
H2A H 0.1617 1.4506 0.9517 0.038 Uiso 1 1 calc R . .
C3 C 0.24270(17) 1.23025(15) 1.00739(8) 0.0269(3) Uani 1 1 d . . .
C4 C 0.3387(2) 1.15716(16) 1.08380(8) 0.0334(3) Uani 1 1 d . . .
H4A H 0.3505 1.0417 1.0874 0.040 Uiso 1 1 calc R . .
C5 C 0.4165(2) 1.25477(18) 1.15436(9) 0.0393(3) Uani 1 1 d . . .
H5A H 0.4845 1.2070 1.2068 0.047 Uiso 1 1 calc R . .
C6 C 0.15347(18) 1.13199(15) 0.92775(8) 0.0277(3) Uani 1 1 d . . .
N2 N 0.04071(16) 0.71486(12) 0.75239(7) 0.0318(3) Uani 1 1 d . . .
H1 H 0.453(2) 1.492(2) 1.1943(11) 0.063(5) 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
N1 0.0355(7) 0.0449(7) 0.0348(6) -0.0141(5) -0.0011(5) -0.0057(5)
O1 0.0454(6) 0.0374(5) 0.0293(5) 0.0031(4) -0.0143(4) 0.0024(4)
O2 0.0453(6) 0.0277(5) 0.0267(5) -0.0017(4) -0.0099(4) 0.0026(4)
O3 0.0553(6) 0.0378(5) 0.0460(6) -0.0150(4) -0.0171(5) -0.0025(5)
O4 0.0791(8) 0.0245(5) 0.0335(5) -0.0046(4) -0.0204(5) 0.0009(5)
O5 0.0664(7) 0.0355(6) 0.0518(6) 0.0154(5) -0.0053(5) 0.0063(5)
C1 0.0380(8) 0.0341(7) 0.0419(8) -0.0061(6) 0.0010(7) -0.0006(6)
C2 0.0315(7) 0.0334(7) 0.0312(7) 0.0012(5) -0.0008(6) 0.0035(6)
C3 0.0253(6) 0.0318(7) 0.0236(6) 0.0007(5) -0.0004(5) 0.0013(5)
C4 0.0392(8) 0.0345(7) 0.0265(6) 0.0012(5) -0.0085(6) 0.0035(6)
C5 0.0373(8) 0.0535(9) 0.0271(7) -0.0018(6) -0.0068(6) 0.0016(7)
C6 0.0293(7) 0.0307(7) 0.0230(6) 0.0026(5) -0.0028(5) 0.0008(5)
N2 0.0356(6) 0.0281(6) 0.0318(6) -0.0005(4) 0.0007(5) -0.0024(5)

_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
N1 C5 1.3342(18) . ?
N1 C1 1.3386(17) . ?
O1 C6 1.2070(14) . ?
O2 C6 1.3191(14) . ?
O3 N2 1.2315(13) . ?
O4 N2 1.2777(13) . ?
O5 N2 1.2255(13) . ?
C1 C2 1.3676(18) . ?
C2 C3 1.3874(17) . ?
C3 C4 1.3872(16) . ?
C3 C6 1.5030(16) . ?
C4 C5 1.3767(18) . ?

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
C5 N1 C1 122.62(12) . . ?
N1 C1 C2 119.76(12) . . ?
C1 C2 C3 119.30(12) . . ?
C4 C3 C2 119.59(11) . . ?
C4 C3 C6 122.03(11) . . ?
C2 C3 C6 118.39(11) . . ?
C5 C4 C3 118.89(12) . . ?
N1 C5 C4 119.84(13) . . ?
O1 C6 O2 125.39(11) . . ?
O1 C6 C3 121.58(11) . . ?
O2 C6 C3 113.02(10) . . ?
O5 N2 O3 123.60(11) . . ?
O5 N2 O4 118.92(11) . . ?
O3 N2 O4 117.47(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.25(19) . . . . ?
N1 C1 C2 C3 0.83(19) . . . . ?
C1 C2 C3 C4 -0.52(18) . . . . ?
C1 C2 C3 C6 178.99(11) . . . . ?
C2 C3 C4 C5 -0.36(18) . . . . ?
C6 C3 C4 C5 -179.84(12) . . . . ?
C1 N1 C5 C4 -0.7(2) . . . . ?
C3 C4 C5 N1 0.94(19) . . . . ?
C4 C3 C6 O1 173.04(12) . . . . ?
C2 C3 C6 O1 -6.46(17) . . . . ?
C4 C3 C6 O2 -6.46(16) . . . . ?
C2 C3 C6 O2 174.05(11) . . . . ?

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 H1 O4 0.96(2) 1.77(2) 2.7346(15) 178(2) 4_686
O2 H2 O4 0.88(2) 1.71(2) 2.5807(12) 170(2) .
C1 H1A O3 0.95 2.50 3.1944(17) 130 4_686
C2 H2A O5 0.95 2.46 3.3756(16) 161 1_565
C4 H4A O3 0.95 2.34 3.1761(16) 147 4_676
C4 H4A O2 0.95 2.46 2.7581(15) 98 .
C5 H5A O1 0.95 2.43 3.1515(17) 132 4_686

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.977

_refine_diff_density_max         0.21
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.04

#===END of CIF

data_(7)
_database_code_depnum_ccdc_archive 'CCDC 688605'
# ZNBPCN

_refine_special_details          
;
The potential lattice centering or halving detected by checkCIF
appears to be only approximate - applying the transformation
results in a much poorer refinement in C2/c.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N2, 2(H2 O4 P), 2(H2 O)'
_chemical_formula_sum            'C10 H18 N2 O10 P2'
_chemical_formula_weight         388.20

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   18.947(3)
_cell_length_b                   9.0330(14)
_cell_length_c                   9.4944(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.736(2)
_cell_angle_gamma                90.00
_cell_volume                     1623.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6255
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13838
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.019
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         27.52
_reflns_number_total             3965
_reflns_number_gt                3308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_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)+(0.0608P)²+1.3077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   
'CH geometrically placed, H2PO4, NH and H2O from delta-F'
_refine_ls_hydrogen_treatment    
'riding model, H2PO4, NH and H2O refined with restraints'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3722
_refine_ls_number_parameters     257
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.124
_refine_ls_wR_factor_gt          0.118
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N Uani 0.10681(8) 0.17691(19) 0.01020(17) 1.000 0.0312(5) . .
N11 N Uani 0.39028(9) 0.2862(2) 0.49551(18) 1.000 0.0360(5) . .
C2 C Uani 0.14707(10) 0.0620(2) 0.0485(2) 1.000 0.0329(5) . .
C3 C Uani 0.20456(10) 0.0804(2) 0.1426(2) 1.000 0.0323(5) . .
C4 C Uani 0.21937(9) 0.2202(2) 0.19836(18) 1.000 0.0261(5) . .
C5 C Uani 0.17595(10) 0.3380(2) 0.1555(2) 1.000 0.0334(5) . .
C6 C Uani 0.11967(11) 0.3127(2) 0.0608(2) 1.000 0.0359(6) . .
C22 C Uani 0.36493(11) 0.1497(2) 0.4748(2) 1.000 0.0381(6) . .
C33 C Uani 0.30903(10) 0.1249(2) 0.3790(2) 1.000 0.0346(6) . .
C44 C Uani 0.28021(9) 0.2438(2) 0.30186(18) 1.000 0.0270(5) . .
C55 C Uani 0.30912(11) 0.3837(2) 0.3243(2) 1.000 0.0351(6) . .
C66 C Uani 0.36431(11) 0.4016(2) 0.4235(2) 1.000 0.0387(6) . .
P1 P Uani 0.03811(2) 0.71631(5) 0.21215(4) 1.000 0.0221(1) . .
O1 O Uani 0.07722(7) 0.71813(15) 0.35251(13) 1.000 0.0316(4) . .
O2 O Uani 0.00348(7) 0.86009(14) 0.16265(13) 1.000 0.0289(3) . .
O3 O Uani 0.09185(8) 0.66577(18) 0.10135(14) 1.000 0.0395(5) . .
O4 O Uani -0.02375(8) 0.60212(17) 0.20695(17) 1.000 0.0431(5) . .
P2 P Uani 0.54072(2) 0.30382(5) 0.21474(4) 1.000 0.0260(2) . .
O5 O Uani 0.57727(8) 0.31183(17) 0.35745(14) 1.000 0.0373(4) . .
O6 O Uani 0.49080(8) 0.17546(18) 0.18698(18) 1.000 0.0502(5) . .
O7 O Uani 0.59914(9) 0.2996(2) 0.10593(16) 1.000 0.0538(6) . .
O8 O Uani 0.49419(11) 0.4412(2) 0.1792(2) 1.000 0.0664(7) . .
O9 O Uani 0.28395(9) 0.6916(3) 0.13783(18) 1.000 0.0551(6) . .
O10 O Uani 0.22177(9) 0.7721(3) 0.3769(2) 1.000 0.0724(8) . .
H1 H Uiso 0.0681(14) 0.157(3) -0.055(3) 1.000 0.050(7) . .
H2A H Uiso 0.13640 -0.03340 0.01120 1.000 0.0390 calc R
H3A H Uiso 0.23360 -0.00170 0.16890 1.000 0.0390 calc R
H5A H Uiso 0.18500 0.43480 0.19110 1.000 0.0400 calc R
H6A H Uiso 0.08980 0.39260 0.03140 1.000 0.0430 calc R
H11 H Uiso 0.4267(17) 0.309(3) 0.565(3) 1.000 0.070(9) . .
H22A H Uiso 0.38550 0.06900 0.52630 1.000 0.0460 calc R
H33A H Uiso 0.29040 0.02800 0.36560 1.000 0.0410 calc R
H55A H Uiso 0.29120 0.46620 0.27200 1.000 0.0420 calc R
H66A H Uiso 0.38380 0.49730 0.44030 1.000 0.0460 calc R
H3B H Uiso 0.0813(16) 0.694(3) 0.0194(15) 1.000 0.066(9) . .
H4B H Uiso -0.0159(14) 0.5197(17) 0.245(3) 1.000 0.060(8) . .
H7B H Uiso 0.5876(17) 0.271(3) 0.0250(16) 1.000 0.074(10) . .
H8B H Uiso 0.5028(17) 0.519(2) 0.225(3) 1.000 0.078(10) . .
H9B H Uiso 0.3206(11) 0.744(3) 0.136(3) 1.000 0.069(10) . .
H9C H Uiso 0.2678(15) 0.716(4) 0.0570(17) 1.000 0.076(10) . .
H10B H Uiso 0.1781(6) 0.757(4) 0.366(3) 1.000 0.067(9) . .
H10C H Uiso 0.2387(15) 0.742(3) 0.302(2) 1.000 0.077(10) . .

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
N1 0.0268(8) 0.0389(9) 0.0271(8) -0.0033(6) -0.0083(6) 0.0004(7)
N11 0.0268(8) 0.0488(10) 0.0314(8) -0.0101(7) -0.0089(7) 0.0021(7)
C2 0.0335(9) 0.0328(9) 0.0316(9) -0.0032(8) -0.0077(7) -0.0024(8)
C3 0.0322(9) 0.0300(9) 0.0335(9) 0.0004(7) -0.0102(7) 0.0025(7)
C4 0.0239(8) 0.0312(9) 0.0228(8) 0.0006(7) -0.0032(6) -0.0006(7)
C5 0.0352(10) 0.0301(9) 0.0336(9) -0.0051(8) -0.0120(8) 0.0036(8)
C6 0.0351(10) 0.0361(10) 0.0353(10) -0.0043(8) -0.0121(8) 0.0080(8)
C22 0.0360(10) 0.0423(11) 0.0346(10) -0.0026(8) -0.0129(8) 0.0069(9)
C33 0.0346(10) 0.0331(10) 0.0347(10) -0.0017(8) -0.0116(8) 0.0014(8)
C44 0.0239(8) 0.0335(9) 0.0232(8) -0.0021(7) -0.0036(6) 0.0010(7)
C55 0.0353(10) 0.0348(10) 0.0344(10) 0.0001(8) -0.0081(8) -0.0027(8)
C66 0.0341(10) 0.0403(11) 0.0406(11) -0.0056(9) -0.0087(8) -0.0054(8)
P1 0.0239(2) 0.0241(2) 0.0177(2) 0.0002(2) -0.0043(2) 0.0006(2)
O1 0.0320(7) 0.0424(8) 0.0198(6) -0.0019(5) -0.0064(5) 0.0011(6)
O2 0.0295(6) 0.0252(6) 0.0309(6) -0.0034(5) -0.0090(5) 0.0040(5)
O3 0.0483(9) 0.0485(8) 0.0220(7) 0.0061(6) 0.0044(6) 0.0221(7)
O4 0.0401(8) 0.0357(8) 0.0512(9) 0.0182(7) -0.0216(7) -0.0129(6)
P2 0.0292(3) 0.0283(3) 0.0197(2) 0.0015(2) -0.0061(2) -0.0012(2)
O5 0.0383(8) 0.0514(9) 0.0212(6) 0.0042(6) -0.0077(5) -0.0033(6)
O6 0.0452(9) 0.0473(9) 0.0552(10) 0.0257(8) -0.0280(7) -0.0206(7)
O7 0.0395(9) 0.0946(14) 0.0273(8) -0.0184(8) 0.0013(6) -0.0184(9)
O8 0.0904(14) 0.0414(9) 0.0624(11) -0.0220(8) -0.0492(10) 0.0264(9)
O9 0.0358(9) 0.0970(15) 0.0320(8) 0.0057(9) -0.0032(7) -0.0067(9)
O10 0.0308(9) 0.150(2) 0.0360(9) -0.0195(11) -0.0025(7) -0.0055(11)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4937(13) . . yes
P1 O2 1.5195(14) . . yes
P1 O3 1.5666(15) . . yes
P1 O4 1.5603(16) . . yes
P2 O5 1.4937(14) . . yes
P2 O6 1.5115(17) . . yes
P2 O7 1.5502(17) . . yes
P2 O8 1.550(2) . . yes
O3 H3B 0.834(17) . . no
O4 H4B 0.838(19) . . no
O7 H7B 0.830(17) . . no
O8 H8B 0.84(2) . . no
O9 H9B 0.84(2) . . no
O9 H9C 0.84(2) . . no
O10 H10B 0.840(13) . . no
O10 H10C 0.84(2) . . no
N1 C2 1.329(2) . . yes
N1 C6 1.336(3) . . yes
N11 C22 1.334(3) . . yes
N11 C66 1.328(3) . . yes
N1 H1 0.95(3) . . no
N11 H11 0.95(3) . . no
C2 C3 1.385(3) . . no
C3 C4 1.393(3) . . no
C4 C44 1.494(2) . . no
C4 C5 1.394(3) . . no
C5 C6 1.381(3) . . no
C22 C33 1.381(3) . . no
C33 C44 1.396(3) . . no
C44 C55 1.390(3) . . no
C55 C66 1.383(3) . . no
C2 H2A 0.9500 . . no
C3 H3A 0.9500 . . no
C5 H5A 0.9500 . . no
C6 H6A 0.9500 . . no
C22 H22A 0.9500 . . no
C33 H33A 0.9500 . . no
C55 H55A 0.9500 . . no
C66 H66A 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O4 112.05(8) . . . yes
O2 P1 O3 109.05(8) . . . yes
O2 P1 O4 104.04(8) . . . yes
O3 P1 O4 107.30(9) . . . yes
O1 P1 O2 117.07(8) . . . yes
O1 P1 O3 106.96(8) . . . yes
O5 P2 O8 113.14(10) . . . yes
O7 P2 O8 106.94(10) . . . yes
O6 P2 O7 109.01(9) . . . yes
O6 P2 O8 103.39(10) . . . yes
O5 P2 O6 117.03(9) . . . yes
O5 P2 O7 106.91(9) . . . yes
P1 O3 H3B 114(2) . . . no
P1 O4 H4B 117.1(18) . . . no
P2 O7 H7B 117(2) . . . no
P2 O8 H8B 118(2) . . . no
H9B O9 H9C 96(3) . . . no
H10B O10 H10C 105(3) . . . no
C2 N1 C6 121.78(17) . . . yes
C22 N11 C66 121.83(18) . . . yes
C2 N1 H1 116.4(16) . . . no
C6 N1 H1 121.9(16) . . . no
C22 N11 H11 123.0(16) . . . no
C66 N11 H11 115.1(16) . . . no
N1 C2 C3 120.42(17) . . . yes
C2 C3 C4 119.46(17) . . . no
C3 C4 C5 118.42(16) . . . no
C5 C4 C44 120.61(16) . . . no
C3 C4 C44 120.97(16) . . . no
C4 C5 C6 119.37(17) . . . no
N1 C6 C5 120.55(17) . . . yes
N11 C22 C33 120.42(17) . . . yes
C22 C33 C44 119.28(17) . . . no
C4 C44 C33 120.36(16) . . . no
C4 C44 C55 121.11(16) . . . no
C33 C44 C55 118.53(16) . . . no
C44 C55 C66 119.37(17) . . . no
N11 C66 C55 120.55(17) . . . yes
C3 C2 H2A 120.00 . . . no
N1 C2 H2A 120.00 . . . no
C2 C3 H3A 120.00 . . . no
C4 C3 H3A 120.00 . . . no
C6 C5 H5A 120.00 . . . no
C4 C5 H5A 120.00 . . . no
N1 C6 H6A 120.00 . . . no
C5 C6 H6A 120.00 . . . no
N11 C22 H22A 120.00 . . . no
C33 C22 H22A 120.00 . . . no
C44 C33 H33A 120.00 . . . no
C22 C33 H33A 120.00 . . . no
C44 C55 H55A 120.00 . . . no
C66 C55 H55A 120.00 . . . no
N11 C66 H66A 120.00 . . . no
C55 C66 H66A 120.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -0.4(3) . . . . no
C2 N1 C6 C5 0.1(3) . . . . no
C66 N11 C22 C33 -1.6(3) . . . . no
C22 N11 C66 C55 0.5(3) . . . . no
N1 C2 C3 C4 0.8(3) . . . . no
C2 C3 C4 C5 -0.9(3) . . . . no
C2 C3 C4 C44 179.01(17) . . . . no
C3 C4 C44 C55 159.53(18) . . . . no
C3 C4 C44 C33 -20.8(3) . . . . no
C5 C4 C44 C33 159.05(18) . . . . no
C5 C4 C44 C55 -20.6(3) . . . . no
C3 C4 C5 C6 0.6(3) . . . . no
C44 C4 C5 C6 -179.35(17) . . . . no
C4 C5 C6 N1 -0.1(3) . . . . no
N11 C22 C33 C44 1.3(3) . . . . no
C22 C33 C44 C55 0.1(3) . . . . no
C22 C33 C44 C4 -179.53(17) . . . . no
C33 C44 C55 C66 -1.2(3) . . . . no
C4 C44 C55 C66 178.44(17) . . . . no
C44 C55 C66 N11 0.9(3) . . . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N1 H1 O2 0.95(3) 1.67(3) 2.616(2) 174(2) 3_565 yes
O3 H3B O1 0.834(17) 1.771(18) 2.5877(19) 166(3) 4_564 yes
O4 H4B O2 0.838(19) 1.70(2) 2.533(2) 174(3) 2_545 yes
O7 H7B O5 0.830(17) 1.760(18) 2.580(2) 169(3) 4_554 yes
O8 H8B O6 0.84(2) 1.64(2) 2.478(2) 173(3) 2_655 yes
O9 H9B O5 0.84(2) 2.03(2) 2.843(2) 163(2) 2_655 yes
O9 H9C O10 0.84(2) 1.885(19) 2.712(3) 167(4) 4_564 yes
O10 H10B O1 0.840(13) 1.942(13) 2.781(2) 177(3) . yes
O10 H10C O9 0.84(2) 1.87(2) 2.706(3) 174(2) . yes
N11 H11 O6 0.95(3) 1.64(3) 2.593(2) 172(3) 4_555 yes

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.67
_refine_diff_density_min         -0.43
_refine_diff_density_rms         0.07

#===END of CIF

#===END


