# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_B102282M _journal_coden_Cambridge 440 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Dr Jon E Matczac' _publ_contact_author_address ;Dr Jon E Matczac Institute of Inorganic Chemistry Wroclaw University of Technology Wybrzeze Wyspianskiego 27 Wroclaw 50-370 POLAND ; _publ_contact_author_email 'JON@ICHN.CH.PWR.WROC.PL' _publ_contact_letter ; Please consider this CIF submision for publication in New Journal of Chemistry ; _publ_requested_journal 'New Journal of Chemistry' # Paper ref. B102282M # TITLE AND AUTHOR LIST _publ_section_title ; Molecular organization and solution properties of N-substituted aminomethane-1,1-diphosphonic acids ; loop_ _publ_author_name _publ_author_address 'Matczak-Jon, Ewa' ; Institute of Inorganic Chemistry Wroc\/law University of Technology 23 Smoluchowskiego St 50-372 Wroc\/law e-mail jon@ichn.ch.pwr.wroc.pl ; 'Sawka-Dobrowolska, Wanda' ; Faculty of Chemistry University of Wroc\/law 14 Joliot-Curie St 50-383 Wroc\/aw Poland ; 'Kafarski, Pawel' ; Institute of Organic Chemistry Biochemistry and Biotechnology Wroc\/law University of Technology 27 Wyb\.zeze Wyspia\'nskiego St Poland ; 'Videnova-Adrabinska, Veneta' ; Institute of Inorganic Chemistry Wroc\/law University of Technology 23 Smoluchowskiego St Poland ; ############################################################################ ### data_I _database_code_CSD 161070 #CHEMICAL DATA _chemical_name_systematic ; N-n-pentylaminomethane-1.1-diphosphonic acid ; _chemical_name_common 'C6 H17 N O6 P2, H2 O' _chemical_formula_moiety 'C6 H17 N O6 P2, H2 O' _chemical_formula_sum 'C6 H19 N O7 P2' _chemical_formula_weight 279.16 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' # CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.374(2) _cell_length_b 10.334(2) _cell_length_c 9.428(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.83(3) _cell_angle_gamma 90.00 _cell_volume 1204.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description 'block' _exptl_crystal_colour 'white' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA KM4CCD k-geometry diffractometer' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8337 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.065 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 28.52 _diffrn_reflns_theta_full 28.52 _reflns_number_total 2894 _reflns_number_gt 1152 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma CCDkM4 software, version 1.63' _computing_cell_refinement 'Kuma CCDKM4 software, version 1.63' _computing_data_reduction 'Kuma CCDKM4 software, version 1.63' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? # REFINEMENT DATA _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0082P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0002(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2894 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0596 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.004 _refine_diff_density_max 0.440 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.068 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.49678(6) 0.18493(7) 0.09658(8) 0.0144(2) Uani 1 d . . . P2 P 0.25554(6) 0.25834(7) 0.02264(8) 0.0162(2) Uani 1 d . . . O1 O 0.54425(14) 0.22924(16) -0.03882(18) 0.0157(5) Uani 1 d . . . O2 O 0.54956(14) 0.07073(15) 0.16903(19) 0.0152(5) Uani 1 d . . . O3 O 0.49141(15) 0.30498(17) 0.1973(2) 0.0163(5) Uani 1 d . . . O4 O 0.21261(15) 0.28590(17) 0.16302(18) 0.0215(5) Uani 1 d . . . O5 O 0.31041(15) 0.36785(18) -0.05448(19) 0.0172(5) Uani 1 d . . . O6 O 0.16629(15) 0.19691(18) -0.0781(2) 0.0177(5) Uani 1 d . . . O7W O 0.35052(16) 0.56087(18) 0.0892(2) 0.0205(5) Uani 1 d . . . N1 N 0.32585(19) 0.0370(2) 0.1633(2) 0.0163(6) Uani 1 d . . . C1 C 0.3586(2) 0.1323(3) 0.0514(3) 0.0140(7) Uani 1 d . . . C2 C 0.2355(2) -0.0538(3) 0.1135(3) 0.0175(7) Uani 1 d . . . C3 C 0.2122(2) -0.1530(3) 0.2252(3) 0.0170(7) Uani 1 d . . . C4 C 0.1312(3) -0.2525(3) 0.1633(3) 0.0174(7) Uani 1 d . . . C5 C 0.1030(3) -0.3555(3) 0.2672(4) 0.0261(8) Uani 1 d . . . C6 C 0.0242(3) -0.4560(3) 0.2043(5) 0.0312(9) Uani 1 d . . . H1 H 0.3606(18) 0.082(2) -0.029(2) 0.015(7) Uiso 1 d . . . H3 H 0.495(2) 0.282(3) 0.292(3) 0.042(10) Uiso 1 d . . . H5 H 0.330(3) 0.449(3) 0.011(4) 0.087(13) Uiso 1 d . . . H6 H 0.184(2) 0.202(2) -0.169(3) 0.031(10) Uiso 1 d . . . H7 H 0.386(3) 0.557(3) 0.191(4) 0.082(17) Uiso 1 d . . . H8 H 0.388(3) 0.642(3) 0.038(4) 0.078(17) Uiso 1 d . . . H11 H 0.305(3) 0.082(3) 0.239(4) 0.062(16) Uiso 1 d . . . H12 H 0.384(3) -0.011(3) 0.192(3) 0.051(13) Uiso 1 d . . . H21 H 0.2576(19) -0.103(2) 0.020(3) 0.022(8) Uiso 1 d . . . H22 H 0.172(2) 0.002(2) 0.077(3) 0.023(8) Uiso 1 d . . . H31 H 0.1838(18) -0.112(2) 0.316(2) 0.016(7) Uiso 1 d . . . H32 H 0.2771(18) -0.196(2) 0.256(2) 0.015(7) Uiso 1 d . . . H41 H 0.1611(18) -0.287(2) 0.082(2) 0.017(7) Uiso 1 d . . . H42 H 0.0626(19) -0.209(2) 0.127(2) 0.019(7) Uiso 1 d . . . H51 H 0.168(2) -0.398(3) 0.303(3) 0.036(10) Uiso 1 d . . . H52 H 0.075(2) -0.308(2) 0.346(3) 0.024(9) Uiso 1 d . . . H61 H -0.052(3) -0.405(3) 0.160(3) 0.060(11) Uiso 1 d . . . H62 H 0.019(2) -0.523(3) 0.272(3) 0.041(10) Uiso 1 d . . . H63 H 0.055(3) -0.493(3) 0.124(3) 0.053(12) Uiso 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 P1 0.0156(4) 0.0124(4) 0.0150(4) 0.0004(3) -0.0002(3) -0.0004(3) P2 0.0174(5) 0.0155(4) 0.0158(4) 0.0010(4) 0.0005(3) 0.0025(4) O1 0.0153(11) 0.0182(11) 0.0137(11) -0.0014(9) 0.0004(8) -0.0071(9) O2 0.0158(12) 0.0121(11) 0.0174(12) 0.0043(9) -0.0025(9) 0.0041(9) O3 0.0257(13) 0.0103(11) 0.0127(12) -0.0033(9) -0.0008(9) 0.0021(9) O4 0.0249(13) 0.0254(13) 0.0145(11) -0.0004(9) 0.0046(9) 0.0115(9) O5 0.0225(12) 0.0115(11) 0.0173(12) 0.0020(9) -0.0022(9) -0.0010(9) O6 0.0172(12) 0.0225(12) 0.0135(12) 0.0020(10) 0.0001(10) -0.0037(9) O7W 0.0218(13) 0.0175(12) 0.0218(13) 0.0014(10) -0.0019(10) -0.0028(9) N1 0.0117(14) 0.0139(13) 0.0231(16) 0.0033(12) -0.0002(12) 0.0000(12) C1 0.0176(18) 0.0146(16) 0.0100(16) 0.0039(13) 0.0024(13) -0.0025(13) C2 0.0134(17) 0.0158(17) 0.0227(19) -0.0023(15) -0.0034(14) -0.0040(14) C3 0.0154(18) 0.0159(17) 0.0195(18) 0.0036(14) -0.0024(14) -0.0003(14) C4 0.0158(18) 0.0170(18) 0.0195(18) 0.0010(15) 0.0014(14) -0.0006(14) C5 0.028(2) 0.023(2) 0.027(2) 0.0051(17) -0.0043(17) -0.0071(17) C6 0.029(2) 0.019(2) 0.045(3) 0.008(2) -0.003(2) -0.0050(17) # MOLECULAR GEOMETRY 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 P1 O2 1.4973(18) . ? P1 O1 1.5028(17) . ? P1 O3 1.5656(19) . ? P1 C1 1.825(3) . ? P2 O4 1.4780(17) . ? P2 O5 1.5228(19) . ? P2 O6 1.556(2) . ? P2 C1 1.834(3) . ? O3 H3 0.92(3) . ? O5 H5 1.06(4) . ? O6 H6 0.89(2) . ? O7W H7 1.03(4) . ? O7W H8 1.08(3) . ? N1 C1 1.512(3) . ? N1 C2 1.516(3) . ? N1 H11 0.90(3) . ? N1 H12 0.90(3) . ? C1 H1 0.92(2) . ? C2 C3 1.508(4) . ? C2 H21 1.07(2) . ? C2 H22 1.02(3) . ? C3 C4 1.531(4) . ? C3 H31 1.03(2) . ? C3 H32 0.95(2) . ? C4 C5 1.499(4) . ? C4 H41 0.94(2) . ? C4 H42 1.01(2) . ? C5 C6 1.525(5) . ? C5 H51 0.97(3) . ? C5 H52 0.97(2) . ? C6 H61 1.14(3) . ? C6 H62 0.95(3) . ? C6 H63 0.94(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 P1 O1 116.59(11) . . ? O2 P1 O3 112.24(11) . . ? O1 P1 O3 107.69(10) . . ? O2 P1 C1 104.72(12) . . ? O1 P1 C1 107.08(12) . . ? O3 P1 C1 108.09(12) . . ? O4 P2 O5 118.22(11) . . ? O4 P2 O6 110.46(11) . . ? O5 P2 O6 109.36(11) . . ? O4 P2 C1 106.41(12) . . ? O5 P2 C1 105.99(12) . . ? O6 P2 C1 105.53(12) . . ? P1 O3 H3 112.2(17) . . ? P2 O5 H5 113.8(17) . . ? P2 O6 H6 111.1(18) . . ? H7 O7W H8 106(2) . . ? C1 N1 C2 113.9(2) . . ? C1 N1 H12 109(2) . . ? C2 N1 H12 109(3) . . ? H11 N1 H12 108(2) . . ? N1 C1 P1 108.14(18) . . ? C1 N1 H11 109(2) . . ? C2 N1 H11 109(3) . . ? N1 C1 P2 110.92(19) . . ? P1 C1 P2 117.34(15) . . ? N1 C1 H1 103.2(14) . . ? P1 C1 H1 107.3(15) . . ? P2 C1 H1 108.9(14) . . ? C3 C2 N1 111.6(2) . . ? C3 C2 H21 108.5(13) . . ? N1 C2 H21 109.7(13) . . ? C3 C2 H22 116.4(14) . . ? N1 C2 H22 107.5(15) . . ? H21 C2 H22 102.6(19) . . ? C2 C3 C4 109.6(2) . . ? C2 C3 H31 112.6(12) . . ? C4 C3 H31 110.4(13) . . ? C2 C3 H32 110.0(14) . . ? C4 C3 H32 109.2(14) . . ? H31 C3 H32 105.0(18) . . ? C5 C4 C3 113.3(3) . . ? C5 C4 H41 112.0(14) . . ? C3 C4 H41 106.9(14) . . ? C5 C4 H42 108.6(13) . . ? C3 C4 H42 110.9(13) . . ? H41 C4 H42 104.7(18) . . ? C4 C5 C6 113.2(3) . . ? C4 C5 H51 109.5(17) . . ? C6 C5 H51 109.7(17) . . ? C4 C5 H52 104.2(15) . . ? C6 C5 H52 113.3(16) . . ? H51 C5 H52 106(2) . . ? C5 C6 H61 109.2(15) . . ? C5 C6 H62 107.7(18) . . ? H61 C6 H62 120(2) . . ? C5 C6 H63 108(2) . . ? H61 C6 H63 105(3) . . ? H62 C6 H63 107(2) . . ? 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 C2 N1 C1 P1 -156.8(2) . . . . ? C2 N1 C1 P2 73.2(3) . . . . ? O2 P1 C1 N1 31.4(2) . . . . ? O1 P1 C1 N1 155.83(17) . . . . ? O3 P1 C1 N1 -88.4(2) . . . . ? O2 P1 C1 P2 157.77(14) . . . . ? O1 P1 C1 P2 -77.84(17) . . . . ? O3 P1 C1 P2 37.93(19) . . . . ? O4 P2 C1 N1 36.4(2) . . . . ? O5 P2 C1 N1 163.11(18) . . . . ? O6 P2 C1 N1 -80.9(2) . . . . ? O4 P2 C1 P1 -88.51(17) . . . . ? O5 P2 C1 P1 38.15(19) . . . . ? O6 P2 C1 P1 154.10(14) . . . . ? C1 N1 C2 C3 175.6(2) . . . . ? N1 C2 C3 C4 -172.8(2) . . . . ? C2 C3 C4 C5 180.0(3) . . . . ? C3 C4 C5 C6 -178.8(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 H11 O5 0.90(3) 2.01(3) 2.852(3) 155(3) 4_566 N1 H11 O4 0.90(3) 2.49(3) 2.929(3) 111(3) . N1 H12 O2 0.90(3) 2.23(3) 2.788(3) 120(3) . O3 H3 O1 0.92(3) 1.68(3) 2.566(3) 159(3) 4_566 O6 H6 O4 0.89(2) 1.65(3) 2.541(2) 178(3) 4_565 O7W H7 O2 1.03(4) 1.52(4) 2.541(3) 170(3) 2_655 O5 H5 O7W 1.06(4) 1.39(4) 2.448(3) 176(3) . O7W H8 O1 1.08(3) 1.57(4) 2.586(3) 153(3) 3_665 C2 H22 O6 1.02(3) 2.49(3) 3.249(4) 130.6(2) . C1 H1 O2 0.92(2) 2.37(2) 3.201(3) 150((2) 3_665 ########################################################################## data_II _database_code_CSD 161071 # CHEMICAL DATA _chemical_name_systematic ; N-pyrrolidinemethane-1,1-diphosphonic acid ; _chemical_name_common 'C5 H13 N O6 P2, H2 O' _chemical_formula_moiety 'C5 H13 N O6 P2, H2 O' _chemical_formula_sum 'C5 H15 N O7 P2' _chemical_formula_weight 263.12 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' # CRYSTAL DATA _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 7.167(1) _cell_length_b 7.535(1) _cell_length_c 10.052(2) _cell_angle_alpha 98.14(1) _cell_angle_beta 99.10(1) _cell_angle_gamma 99.59(1) _cell_volume 520.60(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description 'block' _exptl_crystal_colour 'white' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.436 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma CCDKM4 k-geometry diffractometer' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3652 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 28.74 _diffrn_reflns_theta_full 28.74 _reflns_number_total 2339 _reflns_number_gt 2113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma CCDKM4 software, version 1.63' _computing_cell_refinement 'Kuma CCDKM4 software, version 1.63' _computing_data_reduction 'Kuma CCDKM4 software, version 1.63' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? # REFINEMENT DATA _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.5152P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'refall' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2339 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.009 _refine_diff_density_max 0.389 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.035 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.49181(6) 0.54437(6) 0.29745(4) 0.00762(14) Uani 1 d . . . P2 P 0.30913(6) 0.23299(6) 0.05651(4) 0.00809(14) Uani 1 d . . . O1 O 0.45475(18) 0.69043(17) 0.21426(13) 0.0107(3) Uani 1 d . . . O2 O 0.66063(18) 0.59624(17) 0.41366(13) 0.0112(3) Uani 1 d . . . O3 O 0.30002(18) 0.47291(18) 0.34559(14) 0.0109(3) Uani 1 d . . . O4 O 0.20045(18) 0.37276(17) 0.01085(13) 0.0114(3) Uani 1 d . . . O5 O 0.20814(18) 0.09322(18) 0.12837(13) 0.0116(3) Uani 1 d . . . O6 O 0.38013(19) 0.12470(17) -0.06573(13) 0.0108(3) Uani 1 d . . . O1W O 0.1603(2) -0.23552(19) 0.05607(16) 0.0183(3) Uani 1 d . . . N1 N 0.6437(2) 0.2236(2) 0.23207(15) 0.0086(3) Uani 1 d . . . C1 C 0.5323(2) 0.3568(2) 0.17237(17) 0.0079(3) Uani 1 d . . . C2 C 0.5703(3) 0.1384(2) 0.34807(18) 0.0109(3) Uani 1 d . . . C3 C 0.7491(3) 0.1078(3) 0.4391(2) 0.0191(4) Uani 1 d . . . C4 C 0.9158(3) 0.1514(3) 0.3631(2) 0.0173(4) Uani 1 d . . . C5 C 0.8586(3) 0.2953(3) 0.2826(2) 0.0131(4) Uani 1 d . . . H1 H 0.614(3) 0.412(3) 0.118(2) 0.012(5) Uiso 1 d . . . H2 H 0.638(4) 0.130(4) 0.167(3) 0.019(6) Uiso 1 d . . . H3 H 0.313(4) 0.454(4) 0.421(3) 0.030(7) Uiso 1 d . . . H5 H 0.193(8) -0.031(8) 0.090(6) 0.073(12) Uiso 1 d . . . H6 H 0.421(6) 0.189(5) -0.114(4) 0.056(11) Uiso 1 d . . . H21 H 0.504(3) 0.221(3) 0.393(2) 0.012(5) Uiso 1 d . . . H22 H 0.480(4) 0.026(4) 0.310(3) 0.023(7) Uiso 1 d . . . H31 H 0.776(5) 0.191(5) 0.528(4) 0.054(10) Uiso 1 d . . . H32 H 0.730(4) -0.014(4) 0.454(3) 0.033(8) Uiso 1 d . . . H41 H 0.927(4) 0.043(4) 0.300(3) 0.026(7) Uiso 1 d . . . H42 H 1.037(4) 0.200(4) 0.425(3) 0.024(7) Uiso 1 d . . . H51 H 0.867(4) 0.409(4) 0.338(3) 0.019(6) Uiso 1 d . . . H52 H 0.918(4) 0.303(4) 0.206(3) 0.020(6) Uiso 1 d . . . H7 H 0.239(6) -0.286(6) 0.117(4) 0.063(11) Uiso 1 d . . . H8 H 0.050(7) -0.263(6) 0.091(5) 0.084(14) Uiso 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 P1 0.0097(2) 0.0062(2) 0.0068(2) 0.00125(15) 0.00117(16) 0.00114(15) P2 0.0082(2) 0.0072(2) 0.0083(2) 0.00081(16) 0.00011(16) 0.00149(15) O1 0.0133(6) 0.0077(6) 0.0120(6) 0.0034(5) 0.0018(5) 0.0036(5) O2 0.0114(6) 0.0115(6) 0.0088(6) 0.0012(5) 0.0005(5) -0.0013(5) O3 0.0107(6) 0.0133(6) 0.0089(6) 0.0030(5) 0.0019(5) 0.0017(5) O4 0.0099(6) 0.0090(6) 0.0148(6) 0.0024(5) -0.0013(5) 0.0031(5) O5 0.0127(6) 0.0094(6) 0.0121(6) 0.0015(5) 0.0030(5) -0.0003(5) O6 0.0147(6) 0.0087(6) 0.0090(6) 0.0016(5) 0.0028(5) 0.0022(5) O1W 0.0163(7) 0.0144(7) 0.0239(7) 0.0043(6) 0.0010(6) 0.0043(5) N1 0.0087(7) 0.0083(7) 0.0090(7) 0.0015(5) 0.0011(5) 0.0028(5) C1 0.0085(7) 0.0072(7) 0.0086(7) 0.0024(6) 0.0010(6) 0.0028(6) C2 0.0132(8) 0.0089(8) 0.0113(8) 0.0032(6) 0.0028(7) 0.0023(7) C3 0.0166(9) 0.0242(10) 0.0183(10) 0.0114(8) 0.0002(7) 0.0053(8) C4 0.0148(9) 0.0186(9) 0.0185(9) 0.0056(7) -0.0007(8) 0.0044(7) C5 0.0079(8) 0.0146(9) 0.0163(9) 0.0035(7) 0.0007(7) 0.0015(6) # MOLECULAR GEOMETRY 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 P1 O2 1.4991(13) . ? P1 O1 1.5063(13) . ? P1 O3 1.5656(13) . ? P1 C1 1.8471(17) . ? P2 O4 1.4912(13) . ? P2 O5 1.5105(13) . ? P2 O6 1.5769(13) . ? P2 C1 1.8413(17) . ? O3 H3 0.79(3) . ? O5 H5 0.94(6) . ? O6 H6 0.79(4) . ? O1W H7 0.93(4) . ? O1W H8 0.92(5) . ? N1 C1 1.514(2) . ? N1 C5 1.523(2) . ? N1 C2 1.531(2) . ? N1 H2 0.88(3) . ? C1 H1 0.95(2) . ? C2 C3 1.523(3) . ? C2 H21 0.95(2) . ? C2 H22 0.97(3) . ? C3 C4 1.532(3) . ? C3 H31 0.99(4) . ? C3 H32 0.94(3) . ? C4 C5 1.514(3) . ? C4 H41 0.98(3) . ? C4 H42 0.97(3) . ? C5 H51 0.94(3) . ? C5 H52 0.94(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 P1 O1 116.27(7) . . ? O2 P1 O3 112.19(7) . . ? O1 P1 O3 107.38(7) . . ? O2 P1 C1 109.27(8) . . ? O1 P1 C1 104.21(7) . . ? O3 P1 C1 106.85(8) . . ? O4 P2 O5 117.11(8) . . ? O4 P2 O6 111.74(8) . . ? O5 P2 O6 107.20(7) . . ? O4 P2 C1 107.18(7) . . ? O5 P2 C1 108.38(8) . . ? O6 P2 C1 104.48(7) . . ? P1 O3 H3 115(2) . . ? P2 O5 H5 117(3) . . ? P2 O6 H6 112(3) . . ? H7 O1W H8 97(4) . . ? C1 N1 C5 115.54(13) . . ? C1 N1 C2 116.80(13) . . ? C5 N1 C2 105.89(13) . . ? C1 N1 H2 108.6(17) . . ? C5 N1 H2 104.2(17) . . ? C2 N1 H2 104.5(17) . . ? N1 C1 P2 110.38(11) . . ? N1 C1 P1 115.53(11) . . ? P2 C1 P1 112.90(9) . . ? N1 C1 H1 103.4(14) . . ? P2 C1 H1 107.5(14) . . ? P1 C1 H1 106.2(14) . . ? C3 C2 N1 105.38(14) . . ? C3 C2 H21 113.2(14) . . ? N1 C2 H21 108.1(14) . . ? C3 C2 H22 112.4(16) . . ? N1 C2 H22 109.1(16) . . ? H21 C2 H22 109(2) . . ? C2 C3 C4 106.09(15) . . ? C2 C3 H31 111(2) . . ? C4 C3 H31 109(2) . . ? C2 C3 H32 109.2(19) . . ? C4 C3 H32 112.1(19) . . ? H31 C3 H32 110(3) . . ? C5 C4 C3 103.70(15) . . ? C5 C4 H41 109.6(16) . . ? C3 C4 H41 111.1(17) . . ? C5 C4 H42 109.9(16) . . ? C3 C4 H42 112.0(16) . . ? H41 C4 H42 110(2) . . ? C4 C5 N1 102.11(14) . . ? C4 C5 H51 112.8(16) . . ? N1 C5 H51 104.9(15) . . ? C4 C5 H52 113.3(16) . . ? N1 C5 H52 108.5(16) . . ? H51 C5 H52 114(2) . . ? 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 P2 157.17(12) . . . . ? C2 N1 C1 P2 -77.30(16) . . . . ? C5 N1 C1 P1 -73.23(16) . . . . ? C2 N1 C1 P1 52.31(17) . . . . ? O4 P2 C1 N1 175.58(11) . . . . ? O5 P2 C1 N1 48.34(13) . . . . ? O6 P2 C1 N1 -65.72(12) . . . . ? O4 P2 C1 P1 44.58(11) . . . . ? O5 P2 C1 P1 -82.66(10) . . . . ? O6 P2 C1 P1 163.28(8) . . . . ? O2 P1 C1 N1 33.14(14) . . . . ? O1 P1 C1 N1 158.04(12) . . . . ? O3 P1 C1 N1 -88.47(13) . . . . ? O2 P1 C1 P2 161.51(8) . . . . ? O1 P1 C1 P2 -73.59(10) . . . . ? O3 P1 C1 P2 39.90(11) . . . . ? C1 N1 C2 C3 -148.15(15) . . . . ? C5 N1 C2 C3 -17.92(18) . . . . ? N1 C2 C3 C4 -7.6(2) . . . . ? C2 C3 C4 C5 30.3(2) . . . . ? C3 C4 C5 N1 -40.78(18) . . . . ? C1 N1 C5 C4 167.49(14) . . . . ? C2 N1 C5 C4 36.53(17) . . . . ? H1 C1 N1 H2 -74(2) . . . . ? H1 C1 N1 C5 42.4(15) . . . . ? H1 C1 N1 C2 167.9(15) . . . . ? O2 P1 P2 O6 -51.66(12) . . . . ? O2 P1 P2 O5 78.37(10) . . . . ? O2 P1 P2 O4 -165.38(10) . . . . ? O1 P1 P2 O6 87.65(9) . . . . ? O1 P1 P2 O5 -142.33(7) . . . . ? O1 P1 P2 O4 -26.07(7) . . . . ? O3 P1 P2 O6 -165.23(9) . . . . ? O3 P1 P2 O5 -35.20(7) . . . . ? O3 P1 P2 O4 81.05(7) . . . . ? 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 H2 O6 0.88(3) 2.01(3) 2.869(2) 163(2) 2_655 O3 H3 O2 0.79(3) 1.74(3) 2.5293(19) 178(3) 2_666 O5 H5 O1W 0.94(6) 1.50(6) 2.4310(19) 168(5) . O6 H6 O1 0.79(4) 1.70(4) 2.4836(18) 170(4) 2_665 O1W H7 O1 0.93(4) 1.74(4) 2.622(2) 156(4) 1_545 O1W H7 O4 0.93(4) 2.59(4) 2.991(2) 107(3) 1_545 O1W H8 O4 0.92(5) 1.91(5) 2.563(2) 126(4) 2 C5 H51 O2 0.94(3) 2.34(3) 3.116(2) 139(2) . C5 H52 O1W 0.94(3) 2.56(3) 3.348(3) 141(2) 2_655 C2 H22 O1 0.97(3) 2.54(3) 3.364(2) 144(2) 1_545 C1 H1 O4 0.95(2) 2.55(2) 3.477(3) 166(2) 2_665 C4 H42 O2 0.97(3) 2.60(3) 3.547(2) 167(2) 2_766 ############################################################################ ### data_III _database_code_CSD 161072 # CHEMICAL DATA _chemical_name_systematic ; N-(3-carboxy-2-pyridyl)aminomethane-1,1-diphosphonic acid ; _chemical_formula_moiety 'C7 H10 N2 O8 P2, H2 O' _chemical_formula_sum 'C7 H12 N2 O9 P2' _chemical_formula_weight 330.13 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.128(2) _cell_length_b 8.248(2) _cell_length_c 13.527(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.97(3) _cell_angle_gamma 90.00 _cell_volume 1214.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description 'block' _exptl_crystal_colour 'white' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.408 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA KM$CCD k-geometry diffractometer' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7865 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 28.51 _diffrn_reflns_theta_full 28.51 _reflns_number_total 2855 _reflns_number_gt 2169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma CCDKM4 software, version 1.63' _computing_cell_refinement 'Kuma CCDKM4 software, version 1.63' _computing_data_reduction 'Kuma CCDKM4 software, version 1.63' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? # REFINEMENT DATA _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.2845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'refall' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2855 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.346 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.077 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.12536(6) 0.22466(8) 0.12060(4) 0.01098(16) Uani 1 d . . . P2 P 0.06345(6) 0.13965(8) 0.32687(5) 0.01154(16) Uani 1 d . . . O1 O -0.00926(15) 0.2578(2) 0.08406(12) 0.0137(4) Uani 1 d . . . O2 O 0.19222(15) 0.1509(2) 0.04548(12) 0.0147(4) Uani 1 d . . . O3 O 0.19794(16) 0.3779(2) 0.16735(13) 0.0132(4) Uani 1 d . . . O4 O -0.07239(15) 0.1305(2) 0.28978(12) 0.0140(4) Uani 1 d . . . O5 O 0.11200(17) 0.3103(2) 0.36016(13) 0.0162(4) Uani 1 d . . . O6 O 0.11445(17) 0.0251(2) 0.41579(12) 0.0149(4) Uani 1 d . . . O7 O 0.63855(16) 0.0916(2) 0.43027(14) 0.0181(4) Uani 1 d . . . O8 O 0.47707(16) 0.2340(2) 0.34834(13) 0.0168(4) Uani 1 d . . . O9W O 0.7834(2) 0.3291(3) 0.44424(16) 0.0234(5) Uani 1 d . . . N1 N 0.27486(18) 0.0680(3) 0.26971(15) 0.0125(4) Uani 1 d . . . N2 N 0.2836(2) -0.2121(3) 0.30033(15) 0.0130(4) Uani 1 d . . . C1 C 0.1435(2) 0.0827(3) 0.22733(17) 0.0103(5) Uani 1 d . . . C2 C 0.3370(2) -0.0640(3) 0.30886(17) 0.0109(5) Uani 1 d . . . C3 C 0.4632(2) -0.0551(3) 0.36006(17) 0.0114(5) Uani 1 d . . . C4 C 0.5243(2) -0.1955(3) 0.39391(18) 0.0141(5) Uani 1 d . . . C5 C 0.4656(2) -0.3461(3) 0.38171(18) 0.0151(5) Uani 1 d . . . C6 C 0.3445(2) -0.3504(3) 0.33557(18) 0.0155(5) Uani 1 d . . . C7 C 0.5260(2) 0.1058(3) 0.37794(17) 0.0126(5) Uani 1 d . . . H1 H 0.109(2) -0.016(3) 0.1986(18) 0.018(6) Uiso 1 d . . . H2 H 0.315(2) 0.159(4) 0.282(2) 0.016(7) Uiso 1 d . . . H3 H 0.154(3) 0.449(4) 0.182(2) 0.027(9) Uiso 1 d . . . H4 H 0.212(4) -0.226(5) 0.273(3) 0.058(13) Uiso 1 d . . . H5 H 0.137(4) 0.311(4) 0.422(3) 0.072(14) Uiso 1 d . . . H6 H 0.074(4) -0.057(6) 0.412(3) 0.073(15) Uiso 1 d . . . H7 H 0.677(3) 0.192(4) 0.433(2) 0.041(10) Uiso 1 d . . . H8 H 0.837(3) 0.311(4) 0.479(3) 0.031(11) Uiso 1 d . . . H9 H 0.779(3) 0.447(5) 0.448(3) 0.046(10) Uiso 1 d . . . H14 H 0.611(3) -0.192(4) 0.431(2) 0.025(8) Uiso 1 d . . . H15 H 0.507(3) -0.446(4) 0.405(2) 0.022(7) Uiso 1 d . . . H16 H 0.294(2) -0.443(4) 0.324(2) 0.020(7) Uiso 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 P1 0.0118(3) 0.0109(3) 0.0094(3) 0.0002(2) 0.0004(2) 0.0009(2) P2 0.0128(3) 0.0115(3) 0.0098(3) 0.0014(2) 0.0012(2) 0.0005(2) O1 0.0121(9) 0.0129(9) 0.0142(8) 0.0002(7) -0.0020(7) 0.0009(7) O2 0.0180(9) 0.0150(9) 0.0109(8) 0.0003(7) 0.0028(7) 0.0005(7) O3 0.0122(9) 0.0118(9) 0.0150(9) -0.0024(7) 0.0017(7) -0.0003(7) O4 0.0110(8) 0.0149(9) 0.0164(8) 0.0016(7) 0.0036(7) 0.0022(7) O5 0.0260(10) 0.0133(9) 0.0088(8) 0.0001(7) 0.0023(8) -0.0020(7) O6 0.0180(10) 0.0134(10) 0.0119(8) 0.0034(7) 0.0001(7) -0.0027(8) O7 0.0114(9) 0.0169(10) 0.0236(10) -0.0012(8) -0.0018(7) -0.0017(7) O8 0.0162(9) 0.0136(9) 0.0187(9) 0.0024(7) -0.0009(7) -0.0008(7) O9W 0.0171(11) 0.0174(11) 0.0308(12) 0.0050(9) -0.0062(9) -0.0018(8) N1 0.0109(10) 0.0115(11) 0.0134(10) -0.0009(8) -0.0009(8) -0.0015(9) N2 0.0110(11) 0.0131(11) 0.0131(10) -0.0006(8) -0.0012(8) -0.0008(9) C1 0.0067(11) 0.0118(12) 0.0113(11) -0.0010(9) -0.0010(9) -0.0002(9) C2 0.0117(12) 0.0133(12) 0.0075(10) -0.0017(9) 0.0018(9) 0.0008(10) C3 0.0116(12) 0.0154(13) 0.0075(11) -0.0004(9) 0.0024(9) -0.0011(10) C4 0.0128(13) 0.0170(13) 0.0117(11) -0.0011(10) 0.0005(10) 0.0024(10) C5 0.0190(13) 0.0110(13) 0.0138(12) 0.0019(10) 0.0000(10) 0.0069(10) C6 0.0184(14) 0.0127(13) 0.0148(12) 0.0004(10) 0.0022(10) -0.0001(10) C7 0.0132(12) 0.0160(13) 0.0088(11) 0.0005(9) 0.0031(9) -0.0004(10) # MOLECULAR GEOMETRY 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 P1 O1 1.5019(18) . ? P1 O2 1.5067(18) . ? P1 O3 1.5614(18) . ? P1 C1 1.837(2) . ? P2 O4 1.4925(18) . ? P2 O5 1.5407(19) . ? P2 O6 1.5420(18) . ? P2 C1 1.823(2) . ? O3 H3 0.81(3) . ? O5 H5 0.82(4) . ? O6 H6 0.81(5) . ? O7 C7 1.310(3) . ? O7 H7 0.93(4) . ? O8 C7 1.218(3) . ? O9W H8 0.70(3) . ? O9W H9 0.98(4) . ? N1 C2 1.338(3) . ? N1 C1 1.460(3) . ? N1 H2 0.87(3) . ? N2 C2 1.353(3) . ? N2 C6 1.362(3) . ? N2 H4 0.81(4) . ? C1 H1 0.95(3) . ? C2 C3 1.433(3) . ? C3 C4 1.372(3) . ? C3 C7 1.496(3) . ? C4 C5 1.398(4) . ? C4 H14 0.99(3) . ? C5 C6 1.363(4) . ? C5 H15 0.96(3) . ? C6 H16 0.94(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 P1 O2 116.74(10) . . ? O1 P1 O3 112.51(10) . . ? O2 P1 O3 108.30(10) . . ? O1 P1 C1 108.31(10) . . ? O2 P1 C1 106.46(11) . . ? O3 P1 C1 103.54(10) . . ? O4 P2 O5 114.43(11) . . ? O4 P2 O6 114.49(10) . . ? O5 P2 O6 106.35(10) . . ? O4 P2 C1 110.78(10) . . ? O5 P2 C1 104.80(11) . . ? O6 P2 C1 105.14(11) . . ? P1 O3 H3 113(2) . . ? P2 O6 H6 110(3) . . ? C7 O7 H7 109(2) . . ? H8 O9W H9 103(3) . . ? C2 N1 C1 128.0(2) . . ? C2 N1 H2 115.0(18) . . ? C1 N1 H2 115.7(18) . . ? C2 N2 C6 123.3(2) . . ? C2 N2 H4 123(3) . . ? C6 N2 H4 114(3) . . ? N1 C1 P2 109.52(16) . . ? N1 C1 P1 107.43(16) . . ? P2 C1 P1 115.17(13) . . ? N1 C1 H1 112.4(15) . . ? P2 C1 H1 107.5(15) . . ? P1 C1 H1 104.8(15) . . ? N1 C2 N2 121.2(2) . . ? N1 C2 C3 121.6(2) . . ? N2 C2 C3 117.2(2) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 C7 120.8(2) . . ? C2 C3 C7 120.1(2) . . ? C3 C4 C5 121.6(2) . . ? C3 C4 H14 120.4(18) . . ? C5 C4 H14 118.0(18) . . ? C6 C5 C4 118.1(2) . . ? C6 C5 H15 118.9(17) . . ? C4 C5 H15 123.0(17) . . ? N2 C6 C5 120.8(3) . . ? N2 C6 H16 112.5(17) . . ? C5 C6 H16 126.7(17) . . ? O8 C7 O7 124.5(2) . . ? O8 C7 C3 123.7(2) . . ? O7 C7 C3 111.7(2) . . ? 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 C2 N1 C1 P2 90.2(3) . . . . ? C2 N1 C1 P1 -144.0(2) . . . . ? O4 P2 C1 N1 -171.15(16) . . . . ? O5 P2 C1 N1 64.94(19) . . . . ? O6 P2 C1 N1 -46.96(19) . . . . ? O4 P2 C1 P1 67.66(16) . . . . ? O5 P2 C1 P1 -56.24(15) . . . . ? O6 P2 C1 P1 -168.15(12) . . . . ? O1 P1 C1 N1 -173.01(15) . . . . ? O2 P1 C1 N1 60.70(18) . . . . ? O3 P1 C1 N1 -53.37(18) . . . . ? O1 P1 C1 P2 -50.70(16) . . . . ? O2 P1 C1 P2 -176.99(12) . . . . ? O3 P1 C1 P2 68.94(15) . . . . ? C1 N1 C2 N2 9.6(4) . . . . ? C1 N1 C2 C3 -171.5(2) . . . . ? C6 N2 C2 N1 177.4(2) . . . . ? C6 N2 C2 C3 -1.6(3) . . . . ? N1 C2 C3 C4 -176.5(2) . . . . ? N2 C2 C3 C4 2.5(3) . . . . ? N1 C2 C3 C7 4.8(3) . . . . ? N2 C2 C3 C7 -176.2(2) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? C7 C3 C4 C5 177.2(2) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C2 N2 C6 C5 -0.4(4) . . . . ? C4 C5 C6 N2 1.5(4) . . . . ? C4 C3 C7 O8 178.8(2) . . . . ? C2 C3 C7 O8 -2.5(4) . . . . ? C4 C3 C7 O7 -2.1(3) . . . . ? C2 C3 C7 O7 176.6(2) . . . . ? H1 C1 N1 C2 -29.2(16) . . . . ? H1 C1 N1 H2 165(3) . . . . ? H2 N1 C2 C3 -5(2) . . . . ? H2 N1 C2 N2 176(2) . . . . ? H4 N2 C2 N1 -2(3) . . . . ? C2 N1 H2 O8 4(4) . . . . ? N2 C2 N1 H2 176(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 N1 H2 O8 0.87(3) 1.94(3) 2.660(3) 139(2) . N1 H2 O3 0.87(3) 2.55(3) 2.948(2) 108(2) . N2 H4 O4 0.81(4) 2.00(4) 2.740(3) 152(4) 2_545 O6 H6 O1 0.81(5) 1.69(5) 2.497(3) 170(4) 2_545 O3 H3 O4 0.81(3) 1.83(3) 2.639(3) 172(3) 2 O5 H5 O2 0.82(4) 1.69(4) 2.501(2) 170(4) 4_566 O7 H7 O9W 0.93(4) 1.62(4) 2.519(3) 161(3) . O9W H8 O1 0.70(3) 2.06(4) 2.757(3) 176(4) 4_666 O9W H9 O2 0.98(4) 1.71(4) 2.668(3) 166(3) 2_655 N2 H4 O6 0.81(4) 3.17(4) 3.321(3) 94(3) . C4 H14 O2 0.99(3) 2.51(3) 3.340(3) 141(2) 2_645 ############################################################################ ## data_IV _database_code_CSD 161073 # CHEMICAL DATA _chemical_name_systematic ; N-(5-methyl-2-pyridyl)aminomethane-1,1-diphosphonic acid ; _chemical_formula_moiety 'C7 H12 N2 O6 P2' _chemical_formula_sum 'C7 H12 N2 O6 P2' _chemical_formula_weight 282.13 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _symmetry_cell_setting ' monoclinic' _symmetry_space_group_name_H-M 'P 2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.313(1) _cell_length_b 15.940(3) _cell_length_c 9.421(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.49(3) _cell_angle_gamma 90.00 _cell_volume 1088.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description 'platy shape' _exptl_crystal_colour 'white' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.420 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; The crystals have layered structure and for this reason their quality is bad. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA KM4CCD k-geometry diffractometer' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7790 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 28.66 _diffrn_reflns_theta_full 28.66 _reflns_number_total 7790 _reflns_number_gt 7305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma CCDKM4 software, version 1.63' _computing_cell_refinement 'Kuma CCDKM4 software, version 1.63' _computing_data_reduction 'Kuma CCDKM4 software, version 1.63' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? # REFINEMENT DATA _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0872P)^2^+25.6917P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0084(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(2) _refine_ls_number_reflns 7790 _refine_ls_number_parameters 310 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.2500 _refine_ls_wR_factor_gt 0.2504 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 0.853 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.026 # ATOMIC COORINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P2A P 0.1998(3) 0.23474(13) 0.1834(2) 0.0149(4) Uani 1 d . . . P1A P -0.2266(3) 0.21043(12) 0.1314(2) 0.0167(5) Uani 1 d . . . O1A O -0.2710(9) 0.2902(4) 0.1977(9) 0.0317(17) Uani 1 d . . . O2A O -0.3589(7) 0.1397(4) 0.1502(6) 0.0164(12) Uani 1 d . . . O3A O -0.2084(8) 0.2243(4) -0.0286(6) 0.0229(13) Uani 1 d . . . H3A H -0.2335 0.1808 -0.0730 0.034 Uiso 1 d . . . O4A O 0.2295(7) 0.2354(4) 0.0292(6) 0.0154(11) Uani 1 d . . . O5A O 0.1617(8) 0.3192(4) 0.2536(7) 0.0228(14) Uani 1 d . . . H5A H 0.1903 0.3576 0.2021 0.034 Uiso 1 d . . . O6A O 0.3588(8) 0.1897(5) 0.2804(7) 0.0267(15) Uani 1 d . . . H6A H 0.4128 0.1574 0.2322 0.040 Uiso 1 d . . . N1A N 0.0263(8) 0.0886(4) 0.1512(7) 0.0118(13) Uani 1 d . . . H2A H 0.0606 0.0852 0.0674 0.014 Uiso 1 d . . . N2A N 0.0457(9) -0.0560(4) 0.1558(7) 0.0153(14) Uani 1 d . . . H4A H 0.0777 -0.0525 0.0704 0.018 Uiso 1 d . . . C1A C 0.0007(10) 0.1706(5) 0.2075(9) 0.0137(16) Uani 1 d . . . H1A H -0.0009 0.1644 0.3108 0.016 Uiso 1 calc R . . C2A C 0.0026(9) 0.0167(5) 0.2203(7) 0.0126(14) Uani 1 d . . . C3A C -0.0585(11) 0.0062(5) 0.3518(8) 0.0180(16) Uani 1 d . . . H13A H -0.0971 0.0533 0.3980 0.022 Uiso 1 calc R . . C4A C -0.0650(12) -0.0700(6) 0.4172(9) 0.0219(18) Uani 1 d . . . H14A H -0.1075 -0.0740 0.5058 0.026 Uiso 1 calc R . . C5A C -0.0059(10) -0.1437(5) 0.3487(9) 0.0134(15) Uani 1 d . . . C6A C 0.0407(11) -0.1337(5) 0.2167(8) 0.0151(15) Uani 1 d . . . H16A H 0.0703 -0.1806 0.1656 0.018 Uiso 1 calc R . . C7A C -0.0011(12) -0.2265(5) 0.4219(9) 0.0201(18) Uani 1 d . . . H71A H -0.1213 -0.2393 0.4466 0.030 Uiso 1 calc R . . H72A H 0.0861 -0.2246 0.5073 0.030 Uiso 1 calc R . . H73A H 0.0350 -0.2691 0.3591 0.030 Uiso 1 calc R . . P2B P 0.1992(3) 0.01213(12) -0.2299(2) 0.0146(4) Uani 1 d . . . P1B P 0.6250(3) 0.02673(12) -0.1827(2) 0.0168(4) Uani 1 d . . . O1B O 0.6460(9) -0.0556(4) -0.2540(7) 0.0267(14) Uani 1 d . . . O2B O 0.7617(7) 0.0950(4) -0.2019(7) 0.0223(14) Uani 1 d . . . O3B O 0.6164(8) 0.0123(4) -0.0180(6) 0.0210(12) Uani 1 d . . . H3B H 0.5869 0.0565 0.0186 0.032 Uiso 1 d . . . O4B O 0.1766(8) 0.0071(4) -0.0765(6) 0.0206(12) Uani 1 d . . . O6B O 0.0471(7) 0.0622(4) -0.3217(6) 0.0174(12) Uani 1 d . . . H6B H -0.0509 0.0584 -0.2864 0.026 Uiso 1 d . . . O5B O 0.2171(8) -0.0712(3) -0.3069(6) 0.0164(12) Uani 1 d . . . H5B H 0.1967 -0.1102 -0.2545 0.025 Uiso 1 d . . . N1B N 0.3863(9) 0.1543(4) -0.1930(7) 0.0143(14) Uani 1 d . . . H2B H 0.3394 0.1566 -0.1132 0.017 Uiso 1 d . . . N2B N 0.4140(9) 0.2966(4) -0.1710(7) 0.0162(14) Uani 1 d . . . H4B H 0.3737 0.2908 -0.0897 0.019 Uiso 1 d . . . C1B C 0.4039(10) 0.0714(4) -0.2541(9) 0.0137(16) Uani 1 d . . . H1B H 0.4043 0.0787 -0.3573 0.016 Uiso 1 calc R . . C2B C 0.4336(10) 0.2300(5) -0.2490(8) 0.0141(15) Uani 1 d . . . C3B C 0.4942(11) 0.2381(5) -0.3875(8) 0.0180(16) Uani 1 d . . . H13B H 0.5123 0.1918 -0.4440 0.022 Uiso 1 calc R . . C4B C 0.5237(11) 0.3189(5) -0.4310(9) 0.0189(17) Uani 1 d . . . H14B H 0.5511 0.3269 -0.5237 0.023 Uiso 1 calc R . . C5B C 0.5150(10) 0.3899(5) -0.3439(8) 0.0154(15) Uani 1 d . . . C6B C 0.4602(11) 0.3757(5) -0.2129(9) 0.0188(17) Uani 1 d . . . H16B H 0.4539 0.4205 -0.1505 0.023 Uiso 1 calc R . . C7B C 0.5478(14) 0.4767(6) -0.3927(10) 0.027(2) Uani 1 d . . . H71B H 0.5693 0.5132 -0.3112 0.040 Uiso 1 calc R . . H72B H 0.4417 0.4957 -0.4551 0.040 Uiso 1 calc R . . H73B H 0.6536 0.4772 -0.4432 0.040 Uiso 1 calc R . . 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 P2A 0.0095(8) 0.0175(10) 0.0188(9) -0.0012(9) 0.0067(7) -0.0002(8) P1A 0.0156(10) 0.0088(9) 0.0271(11) -0.0012(8) 0.0079(8) 0.0015(8) O1A 0.026(3) 0.014(3) 0.056(5) -0.016(3) 0.010(3) 0.004(3) O2A 0.010(3) 0.020(3) 0.021(3) 0.001(2) 0.006(2) -0.001(2) O3A 0.031(3) 0.015(3) 0.023(3) 0.009(3) 0.005(3) -0.004(3) O4A 0.010(2) 0.019(3) 0.019(3) 0.000(3) 0.009(2) 0.004(2) O5A 0.022(3) 0.020(3) 0.029(3) -0.003(3) 0.015(3) -0.007(2) O6A 0.015(3) 0.043(4) 0.023(3) 0.013(3) 0.006(2) -0.006(3) N1A 0.012(3) 0.010(3) 0.014(3) -0.002(3) 0.003(3) -0.007(2) N2A 0.015(3) 0.014(3) 0.017(3) 0.000(3) 0.003(3) -0.008(3) C1A 0.007(3) 0.019(4) 0.016(4) 0.006(3) 0.007(3) 0.009(3) C2A 0.009(3) 0.016(3) 0.012(3) -0.002(3) -0.001(3) 0.000(3) C3A 0.022(4) 0.015(4) 0.018(4) -0.004(3) 0.007(3) 0.001(3) C4A 0.026(4) 0.024(4) 0.015(4) -0.001(4) 0.002(3) 0.001(4) C5A 0.005(3) 0.011(3) 0.023(4) 0.002(3) 0.001(3) -0.005(3) C6A 0.020(4) 0.011(3) 0.014(3) -0.007(3) 0.000(3) 0.007(3) C7A 0.024(4) 0.013(4) 0.022(4) 0.006(3) -0.002(3) 0.001(3) P2B 0.0175(9) 0.0112(9) 0.0157(9) 0.0014(9) 0.0048(7) -0.0015(8) P1B 0.0183(10) 0.0123(10) 0.0200(10) -0.0001(9) 0.0033(8) 0.0064(8) O1B 0.039(4) 0.013(3) 0.028(3) -0.003(3) 0.000(3) 0.001(3) O2B 0.008(2) 0.031(3) 0.029(3) 0.010(3) 0.007(2) 0.011(2) O3B 0.027(3) 0.012(3) 0.022(3) -0.002(3) -0.005(2) -0.002(3) O4B 0.026(3) 0.014(3) 0.023(3) -0.005(3) 0.009(2) 0.000(3) O6B 0.010(2) 0.018(3) 0.025(3) 0.003(2) 0.002(2) -0.001(2) O5B 0.021(3) 0.007(2) 0.022(3) 0.003(2) 0.006(2) 0.002(2) N1B 0.017(3) 0.010(3) 0.018(3) 0.000(3) 0.008(3) 0.000(3) N2B 0.017(3) 0.021(4) 0.012(3) 0.000(3) 0.007(3) 0.001(3) C1B 0.010(3) 0.000(3) 0.031(4) 0.003(3) 0.006(3) 0.004(3) C2B 0.010(3) 0.015(4) 0.017(4) 0.003(3) 0.000(3) -0.002(3) C3B 0.028(4) 0.013(4) 0.015(3) -0.003(3) 0.012(3) -0.001(3) C4B 0.020(4) 0.018(4) 0.019(4) 0.004(3) 0.006(3) 0.007(3) C5B 0.011(3) 0.019(4) 0.016(4) -0.001(3) -0.003(3) 0.003(3) C6B 0.022(4) 0.007(3) 0.029(4) -0.002(3) 0.011(4) 0.002(3) C7B 0.037(5) 0.019(4) 0.024(4) 0.012(4) 0.001(4) -0.001(4) # MOLECULAR GEOMETRY 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 P2A O4A 1.497(5) . ? P2A O5A 1.541(6) . ? P2A O6A 1.558(6) . ? P2A C1A 1.817(8) . ? P1A O1A 1.472(6) . ? P1A O2A 1.511(6) . ? P1A O3A 1.546(6) . ? P1A C1A 1.836(7) . ? O3A H3A 0.8186 . ? O5A H5A 0.8255 . ? O6A H6A 0.8212 . ? N1A C2A 1.341(10) . ? N1A C1A 1.432(10) . ? N1A H2A 0.8608 . ? N2A C2A 1.363(10) . ? N2A C6A 1.368(10) . ? N2A H4A 0.8691 . ? C1A H1A 0.9800 . ? C2A C3A 1.381(10) . ? C3A C4A 1.366(12) . ? C3A H13A 0.9300 . ? C4A C5A 1.434(11) . ? C4A H14A 0.9300 . ? C5A C6A 1.341(11) . ? C5A C7A 1.487(11) . ? C6A H16A 0.9300 . ? C7A H71A 0.9600 . ? C7A H72A 0.9600 . ? C7A H73A 0.9600 . ? P2B O4B 1.478(6) . ? P2B O5B 1.528(6) . ? P2B O6B 1.540(6) . ? P2B C1B 1.809(8) . ? P1B O1B 1.490(6) . ? P1B O2B 1.505(6) . ? P1B O3B 1.578(6) . ? P1B C1B 1.814(7) . ? O3B H3B 0.8255 . ? O6B H6B 0.8305 . ? O5B H5B 0.8192 . ? N1B C2B 1.379(10) . ? N1B C1B 1.453(10) . ? N1B H2B 0.8667 . ? N2B C2B 1.309(11) . ? N2B C6B 1.376(10) . ? N2B H4B 0.8611 . ? C1B H1B 0.9800 . ? C2B C3B 1.438(10) . ? C3B C4B 1.377(12) . ? C3B H13B 0.9300 . ? C4B C5B 1.404(11) . ? C4B H14B 0.9300 . ? C5B C6B 1.366(11) . ? C5B C7B 1.488(12) . ? C6B H16B 0.9300 . ? C7B H71B 0.9600 . ? C7B H72B 0.9600 . ? C7B H73B 0.9600 . ? 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 O4A P2A O5A 117.9(4) . . ? O4A P2A O6A 112.4(3) . . ? O5A P2A O6A 108.3(4) . . ? O4A P2A C1A 110.2(3) . . ? O5A P2A C1A 104.2(3) . . ? O6A P2A C1A 102.5(3) . . ? O1A P1A O2A 114.6(4) . . ? O1A P1A O3A 110.0(4) . . ? O2A P1A O3A 111.0(3) . . ? O1A P1A C1A 111.8(4) . . ? O2A P1A C1A 104.9(3) . . ? O3A P1A C1A 104.0(3) . . ? P1A O3A H3A 109.6 . . ? P2A O5A H5A 108.8 . . ? P2A O6A H6A 109.9 . . ? C2A N1A C1A 124.7(7) . . ? C2A N1A H2A 117.6 . . ? C1A N1A H2A 117.7 . . ? C2A N2A C6A 124.2(7) . . ? C2A N2A H4A 117.7 . . ? C6A N2A H4A 118.2 . . ? N1A C1A P2A 108.8(5) . . ? N1A C1A P1A 109.1(5) . . ? P2A C1A P1A 117.1(4) . . ? N1A C1A H1A 107.1 . . ? P2A C1A H1A 107.1 . . ? P1A C1A H1A 107.1 . . ? N1A C2A N2A 117.2(6) . . ? N1A C2A C3A 128.0(8) . . ? N2A C2A C3A 114.7(7) . . ? C4A C3A C2A 123.1(8) . . ? C4A C3A H13A 118.4 . . ? C2A C3A H13A 118.4 . . ? C3A C4A C5A 119.7(8) . . ? C3A C4A H14A 120.1 . . ? C5A C4A H14A 120.1 . . ? C6A C5A C4A 116.6(7) . . ? C6A C5A C7A 122.8(7) . . ? C4A C5A C7A 120.6(7) . . ? C5A C6A N2A 121.4(7) . . ? C5A C6A H16A 119.3 . . ? N2A C6A H16A 119.3 . . ? C5A C7A H71A 109.5 . . ? C5A C7A H72A 109.5 . . ? H71A C7A H72A 109.5 . . ? C5A C7A H73A 109.5 . . ? H71A C7A H73A 109.5 . . ? H72A C7A H73A 109.5 . . ? O4B P2B O5B 116.4(3) . . ? O4B P2B O6B 114.4(3) . . ? O5B P2B O6B 106.5(3) . . ? O4B P2B C1B 110.5(4) . . ? O5B P2B C1B 105.7(3) . . ? O6B P2B C1B 102.0(3) . . ? O1B P1B O2B 118.3(4) . . ? O1B P1B O3B 109.5(4) . . ? O2B P1B O3B 109.6(3) . . ? O1B P1B C1B 108.6(4) . . ? O2B P1B C1B 104.2(3) . . ? O3B P1B C1B 105.9(4) . . ? P1B O3B H3B 109.4 . . ? P2B O6B H6B 109.6 . . ? P2B O5B H5B 109.8 . . ? C2B N1B C1B 127.2(7) . . ? C2B N1B H2B 116.2 . . ? C1B N1B H2B 116.6 . . ? C2B N2B C6B 122.2(7) . . ? C2B N2B H4B 119.2 . . ? C6B N2B H4B 118.6 . . ? N1B C1B P2B 107.9(5) . . ? N1B C1B P1B 109.3(5) . . ? P2B C1B P1B 117.4(4) . . ? N1B C1B H1B 107.2 . . ? P2B C1B H1B 107.2 . . ? P1B C1B H1B 107.2 . . ? N2B C2B N1B 116.4(7) . . ? N2B C2B C3B 120.4(7) . . ? N1B C2B C3B 123.2(7) . . ? C4B C3B C2B 115.7(7) . . ? C4B C3B H13B 122.2 . . ? C2B C3B H13B 122.2 . . ? C3B C4B C5B 124.0(8) . . ? C3B C4B H14B 118.0 . . ? C5B C4B H14B 118.0 . . ? C6B C5B C4B 115.8(7) . . ? C6B C5B C7B 120.8(8) . . ? C4B C5B C7B 123.2(8) . . ? C5B C6B N2B 121.5(7) . . ? C5B C6B H16B 119.2 . . ? N2B C6B H16B 119.2 . . ? C5B C7B H71B 109.5 . . ? C5B C7B H72B 109.5 . . ? H71B C7B H72B 109.5 . . ? C5B C7B H73B 109.5 . . ? H71B C7B H73B 109.5 . . ? H72B C7B H73B 109.5 . . ? 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 C2A N1A C1A P2A 131.5(6) . . . . ? C2A N1A C1A P1A -99.7(7) . . . . ? O4A P2A C1A N1A 55.2(6) . . . . ? O5A P2A C1A N1A -177.4(5) . . . . ? O6A P2A C1A N1A -64.6(6) . . . . ? O4A P2A C1A P1A -69.0(5) . . . . ? O5A P2A C1A P1A 58.4(5) . . . . ? O6A P2A C1A P1A 171.2(5) . . . . ? O1A P1A C1A N1A 173.2(5) . . . . ? O2A P1A C1A N1A 48.5(6) . . . . ? O3A P1A C1A N1A -68.2(6) . . . . ? O1A P1A C1A P2A -62.7(6) . . . . ? O2A P1A C1A P2A 172.5(4) . . . . ? O3A P1A C1A P2A 55.9(5) . . . . ? C1A N1A C2A N2A -175.3(7) . . . . ? C1A N1A C2A C3A 3.6(12) . . . . ? C6A N2A C2A N1A 175.4(7) . . . . ? C6A N2A C2A C3A -3.6(11) . . . . ? N1A C2A C3A C4A -175.1(8) . . . . ? N2A C2A C3A C4A 3.9(11) . . . . ? C2A C3A C4A C5A 0.2(13) . . . . ? C3A C4A C5A C6A -4.7(12) . . . . ? C3A C4A C5A C7A 176.3(8) . . . . ? C4A C5A C6A N2A 5.1(11) . . . . ? C7A C5A C6A N2A -175.9(7) . . . . ? C2A N2A C6A C5A -0.9(12) . . . . ? C2B N1B C1B P2B -139.0(7) . . . . ? C2B N1B C1B P1B 92.3(8) . . . . ? O4B P2B C1B N1B -57.9(6) . . . . ? O5B P2B C1B N1B 175.2(5) . . . . ? O6B P2B C1B N1B 64.1(6) . . . . ? O4B P2B C1B P1B 66.1(6) . . . . ? O5B P2B C1B P1B -60.7(6) . . . . ? O6B P2B C1B P1B -171.9(5) . . . . ? O1B P1B C1B N1B -176.1(5) . . . . ? O2B P1B C1B N1B -49.2(6) . . . . ? O3B P1B C1B N1B 66.3(6) . . . . ? O1B P1B C1B P2B 60.5(6) . . . . ? O2B P1B C1B P2B -172.6(5) . . . . ? O3B P1B C1B P2B -57.0(5) . . . . ? C6B N2B C2B N1B 178.5(7) . . . . ? C6B N2B C2B C3B -4.0(11) . . . . ? C1B N1B C2B N2B -176.7(7) . . . . ? C1B N1B C2B C3B 5.9(12) . . . . ? N2B C2B C3B C4B -1.7(11) . . . . ? N1B C2B C3B C4B 175.7(7) . . . . ? C2B C3B C4B C5B 6.3(12) . . . . ? C3B C4B C5B C6B -5.0(12) . . . . ? C3B C4B C5B C7B 179.8(8) . . . . ? C4B C5B C6B N2B -1.0(12) . . . . ? C7B C5B C6B N2B 174.3(8) . . . . ? C2B N2B C6B C5B 5.4(12) . . . . ? H1A C1A N1A C2A 16.0 . . . . ? H1A C1A N1A H2A -163.4 . . . . ? H2A N1A C2A N2A 4.0 . . . . ? H1B C1B N1B C2B -23.7 . . . . ? H1B C1B N1B H2B 155.2 . . . . ? H2B N1B C2B N2B 4.4 . . . . ? H4A N2A C2A N1A -4.9 . . . . ? H4B N2B C2B N1B 0.2 . . . . ? 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 O3A H3A O2B 0.82 1.83 2.620(9) 163.4 1_455 O5A H5A O1B 0.83 1.85 2.442(8) 127.2 2_655 O6A H6A O2A 0.82 1.95 2.658(8) 144.0 1_655 N1A H2A O4B 0.86 2.10 2.848(9) 145.2 . N2A H4A O4B 0.87 1.90 2.695(9) 151.9 . O3B H3B O2A 0.83 1.82 2.567(8) 149.2 1_655 O5B H5B O1A 0.82 1.74 2.447(8) 143.4 2_545 O6B H6B O2B 0.83 1.77 2.553(8) 156.2 1_455 N1B H2B O4A 0.87 2.07 2.827(8) 144.8 . N2B H4B O4A 0.86 1.86 2.644(9) 150.9 . C6B H16B O3B 0.93 2.27 3.179(10) 167 2_545 C6A H16A O3A 0.93 2.31 3.215(9) 165 2_655 #END_OF_CIF_FILE