# 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>2\s(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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0249P)^2^+1.0947P] where P=(Fo^2^+2Fc^2^)/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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0268P)^2^+0.3448P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0320P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0509P)^2^+1.4883P] where P=(Fo^2^+2Fc^2^)/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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0442P)^2^+2.1617P] where P=(Fo^2^+2Fc^2^)/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/[\s^2^(Fo^2^)+(0.036P)^2^] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0608P)^2^+1.3077P] where P=(Fo^2^+2Fc^2^)/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