#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013326.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013326 loop_ _publ_author_name 'Fern\'andez, Daniel' 'Vega, Daniel' _publ_section_title ; Head-to-head dimers in the zwitterion of 1-hydroxy-3-(pyrrolidin-1-yl)propylidene-1,1-bisphosphonic acid (EB 1053) ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o228 _journal_page_last o230 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C7 H17 N O7 P2' _chemical_formula_moiety 'C7 H17 N O7 P2' _chemical_formula_sum 'C7 H17 N O7 P2' _chemical_formula_weight 289.16 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 106.439(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9208(16) _cell_length_b 10.7754(19) _cell_length_c 11.4933(17) _cell_measurement_reflns_used 20 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 17.5 _cell_measurement_theta_min 10 _cell_volume 1178.4(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software version 4.3.0 (Molecular Structure Corporation, 1993) ; _computing_data_reduction 'MSC/AFC Diffractometer Control Software' _computing_molecular_graphics 'XP in SHELXTL/PC (Sheldrick, 1991)' _computing_publication_material ; CSD (Allen, 2002), PARST (Nardelli, 1995) and WinGX (Farrugia, 1999) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Rigaku AFC-6S diffractometer' _diffrn_measurement_method '\w-2\q scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8063 _diffrn_reflns_theta_full 28.5 _diffrn_reflns_theta_max 28.5 _diffrn_reflns_theta_min 2.86 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 400 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.9507 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(Molecular Structure Corporation, 1993)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.63 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.375 _refine_diff_density_min -0.302 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2992 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_gt 0.037 _refine_ls_shift/su_max 0.004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.055P)^2^+0.191P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1029 _reflns_number_gt 2436 _reflns_number_total 2992 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1602.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2013326 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.75896(19) 0.07792(16) 0.28198(15) 0.0225(3) Uani d . 1 . . C C2 0.6193(2) 0.0113(2) 0.21496(18) 0.0291(4) Uani d . 1 . . C H6 0.555(3) 0.078(2) 0.183(2) 0.035 Uiso d . 1 . . H H7 0.635(3) -0.036(2) 0.150(2) 0.035 Uiso d . 1 . . H C3 0.5545(2) -0.06834(18) 0.29462(17) 0.0275(4) Uani d . 1 . . C H8 0.623(3) -0.112(2) 0.355(2) 0.033 Uiso d . 1 . . H H9 0.499(3) -0.017(2) 0.332(2) 0.033 Uiso d . 1 . . H C4 0.3380(3) -0.1132(3) 0.1194(2) 0.0485(6) Uani d . 1 . . C H10 0.309(3) -0.035(3) 0.150(3) 0.058 Uiso d . 1 . . H H11 0.370(3) -0.088(3) 0.058(3) 0.058 Uiso d . 1 . . H C5 0.2243(4) -0.2095(4) 0.1004(3) 0.0468(8) Uani d P 0.75 A . C H12 0.1326 -0.1723 0.0658 0.056 Uiso calc PR 0.75 . . H H13 0.2382 -0.2743 0.0463 0.056 Uiso calc PR 0.75 . . H C6 0.2357(3) -0.2609(3) 0.2230(3) 0.0579(7) Uani d . 1 . . C H14 0.165(4) -0.242(3) 0.256(3) 0.07 Uiso d . 1 . . H H15 0.221(4) -0.352(3) 0.207(3) 0.07 Uiso d . 1 . . H C7 0.3834(2) -0.2364(2) 0.3021(2) 0.0360(5) Uani d . 1 A . C H16 0.388(3) -0.187(2) 0.371(2) 0.043 Uiso d . 1 . . H H17 0.441(3) -0.310(2) 0.332(2) 0.043 Uiso d . 1 . . H N1 0.45500(17) -0.16347(15) 0.22290(15) 0.0272(3) Uani d . 1 A . N H1 0.502(3) -0.213(2) 0.193(2) 0.031(6) Uiso d . 1 . . H O1 0.62166(15) 0.22618(13) 0.39846(13) 0.0318(3) Uani d . 1 . . O O2 0.75354(15) 0.04549(12) 0.51885(12) 0.0280(3) Uani d . 1 . . O O3 0.88467(16) 0.23296(12) 0.46987(13) 0.0307(3) Uani d D 1 . . O H3 0.948(3) 0.198(2) 0.515(2) 0.046 Uiso d D 1 . . H O4 0.90805(18) -0.05177(13) 0.16250(13) 0.0351(3) Uani d D 1 . . O H4 0.893(3) -0.126(2) 0.142(3) 0.053 Uiso d D 1 . . H O5 1.03790(15) 0.05755(12) 0.35421(13) 0.0303(3) Uani d D 1 . . O H5 1.111(3) 0.013(2) 0.406(2) 0.046 Uiso d D 1 . . H O6 0.90106(14) -0.13984(11) 0.36609(11) 0.0255(3) Uani d . 1 . . O O7 0.78496(15) 0.17743(12) 0.20774(12) 0.0282(3) Uani d . 1 . . O H2 0.721(3) 0.227(2) 0.191(2) 0.038(7) Uiso d . 1 . . H P1 0.75118(5) 0.14756(4) 0.42707(4) 0.02320(13) Uani d . 1 . . P P2 0.91059(5) -0.02418(4) 0.29530(4) 0.02260(13) Uani d . 1 . . P C5' 0.2102(10) -0.1424(11) 0.1407(13) 0.057(3) Uani d P 0.25 A 1 C H12' 0.1393 -0.1587 0.0647 0.068 Uiso calc PR 0.25 A 1 H H13' 0.1785 -0.0741 0.1812 0.068 Uiso calc PR 0.25 A 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0212(8) 0.0223(8) 0.0232(8) 0.0004(7) 0.0051(7) 0.0033(6) C2 0.0219(9) 0.0347(10) 0.0273(8) -0.0019(8) 0.0013(7) 0.0007(8) C3 0.0233(9) 0.0297(9) 0.0279(9) -0.0032(8) 0.0046(8) -0.0047(7) C4 0.0329(12) 0.0584(15) 0.0442(13) -0.0082(12) -0.0057(10) 0.0056(12) C5 0.0285(16) 0.054(2) 0.0513(19) -0.0069(15) 0.0005(14) -0.0114(16) C6 0.0331(13) 0.078(2) 0.0658(17) -0.0196(13) 0.0193(13) -0.0078(15) C7 0.0349(11) 0.0402(11) 0.0376(11) -0.0097(9) 0.0181(9) -0.0073(9) N1 0.0210(8) 0.0330(8) 0.0280(7) -0.0013(7) 0.0075(6) -0.0055(6) O1 0.0283(7) 0.0322(7) 0.0356(7) 0.0080(6) 0.0102(6) 0.0054(6) O2 0.0264(7) 0.0304(7) 0.0263(6) 0.0014(5) 0.0060(5) 0.0056(5) O3 0.0297(7) 0.0263(7) 0.0324(7) -0.0025(6) 0.0028(6) 0.0007(5) O4 0.0516(10) 0.0279(7) 0.0296(7) 0.0022(7) 0.0175(7) 0.0002(5) O5 0.0224(7) 0.0243(6) 0.0397(7) -0.0008(5) 0.0011(6) 0.0054(6) O6 0.0254(7) 0.0220(6) 0.0265(6) -0.0019(5) 0.0030(5) 0.0016(5) O7 0.0273(7) 0.0258(6) 0.0330(7) 0.0067(6) 0.0109(6) 0.0111(5) P1 0.0225(2) 0.0227(2) 0.0237(2) 0.00221(18) 0.00551(18) 0.00219(16) P2 0.0221(2) 0.0205(2) 0.0244(2) 0.00094(17) 0.00534(18) 0.00126(16) C5' 0.019(4) 0.058(7) 0.090(9) 0.008(4) 0.009(5) -0.005(6) 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 0 '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 0.006 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O7 C1 C2 109.50(14) ? O7 C1 P2 102.48(12) ? C2 C1 P2 111.03(13) ? O7 C1 P1 107.01(11) ? C2 C1 P1 112.01(13) ? P1 C1 P2 114.23(9) y C3 C2 C1 115.48(15) ? C3 C2 H6 107.9(14) ? C1 C2 H6 104.1(14) ? C3 C2 H7 110.9(14) ? C1 C2 H7 108.6(15) ? H6 C2 H7 109(2) ? N1 C3 C2 112.29(15) ? N1 C3 H8 106.7(14) ? C2 C3 H8 112.5(15) ? N1 C3 H9 105.4(14) ? C2 C3 H9 109.6(14) ? H8 C3 H9 110(2) ? C5' C4 N1 108.4(6) ? C5 C4 N1 104.2(2) ? C5' C4 H10 76.3(19) ? C5 C4 H10 111.3(18) ? N1 C4 H10 105.1(18) ? C5' C4 H11 139(2) ? C5 C4 H11 121(2) ? N1 C4 H11 111(2) ? H10 C4 H11 103(3) ? C6 C5 C4 105.4(2) ? C6 C5 H12 110.7 ? C4 C5 H12 110.7 ? C6 C5 H13 110.7 ? C4 C5 H13 110.7 ? H12 C5 H13 108.8 ? C5 C6 C7 107.8(2) ? C7 C6 C5' 100.6(4) ? C5 C6 H14 117(2) ? C7 C6 H14 116(2) ? C5' C6 H14 93(2) ? C5 C6 H15 103.0(19) ? C7 C6 H15 110(2) ? C5' C6 H15 134(2) ? H14 C6 H15 102(3) ? C6 C7 N1 105.50(19) ? C6 C7 H16 114.2(16) ? N1 C7 H16 106.7(15) ? C6 C7 H17 116.0(15) ? N1 C7 H17 107.7(15) ? H16 C7 H17 106(2) ? C3 N1 C4 115.38(17) ? C3 N1 C7 111.74(15) ? C4 N1 C7 105.78(17) ? C3 N1 H1 107.8(16) ? C4 N1 H1 107.0(16) ? C7 N1 H1 108.9(16) ? P1 O3 H3 112(2) ? P2 O4 H4 114(2) ? P2 O5 H5 112.3(16) ? C1 O7 H2 112.1(18) ? O1 P1 O2 113.96(8) y O1 P1 O3 109.41(8) y O2 P1 O3 111.11(8) y O1 P1 C1 106.49(8) ? O2 P1 C1 109.62(8) ? O3 P1 C1 105.84(8) ? O4 P2 O5 109.12(9) y O4 P2 O6 112.81(8) y O5 P2 O6 114.02(7) y O6 P2 C1 111.47(8) ? O5 P2 C1 104.26(8) ? O4 P2 C1 104.40(8) ? C4 C5' C6 106.9(6) ? C4 C5' H12' 110.3 ? C6 C5' H12' 110.3 ? C4 C5' H13' 110.3 ? C6 C5' H13' 110.3 ? H12' C5' H13' 108.6 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 O7 1.438(2) y C1 C2 1.557(3) ? C1 P1 1.8501(18) y C1 P2 1.8348(18) y C2 C3 1.524(3) ? C2 H6 0.97(2) ? C2 H7 0.95(2) ? C3 N1 1.498(2) y C3 H8 0.94(2) ? C3 H9 0.96(3) ? C4 C5' 1.394(11) ? C4 C5 1.503(4) ? C4 N1 1.508(3) y C4 H10 0.99(3) ? C4 H11 0.90(3) ? C5 C6 1.489(5) ? C5 H12 0.97 ? C5 H13 0.97 ? C6 C7 1.513(3) ? C6 C5' 1.567(12) ? C6 H14 0.91(4) ? C6 H15 1.00(3) ? C7 N1 1.522(3) y C7 H16 0.94(3) ? C7 H17 0.98(3) ? N1 H1 0.85(2) ? O1 P1 1.4959(14) y O2 P1 1.5194(13) y O3 P1 1.5729(15) y O3 H3 0.79(2) ? O4 P2 1.5482(15) y O4 H4 0.83(2) ? O5 P2 1.5314(14) y O5 H5 0.93(2) ? O6 P2 1.5060(13) y O7 H2 0.81(3) ? C5' H12' 0.97 ? C5' H13' 0.97 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O7 H2 O6 2_655 0.81(3) 1.87(3) 2.668(2) 167(3) O5 H5 O2 3_756 0.93(2) 1.51(2) 2.436(2) 170(3) O3 H3 O6 3_756 0.79(2) 1.83(2) 2.610(2) 171(3) O4 H4 O1 2_645 0.83(2) 1.66(2) 2.487(2) 175(3) N1 H1 O3 2_645 0.85(2) 2.51(3) 3.268(2) 150(2) N1 H1 O5 2_645 0.85(2) 2.54(2) 3.141(2) 129(2) N1 H1 O7 2_645 0.85(2) 2.41(2) 3.011(2) 129(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_publ_flag O7 C1 C2 C3 -162.10(16) ? P2 C1 C2 C3 85.46(19) ? P1 C1 C2 C3 -43.6(2) ? C1 C2 C3 N1 -159.04(16) ? N1 C4 C5 C6 33.3(3) ? C4 C5 C6 C7 -22.4(4) ? C5 C6 C7 N1 2.7(3) ? C5' C6 C7 N1 -31.4(6) ? C2 C3 N1 C4 -55.2(2) ? C2 C3 N1 C7 -176.07(17) ? C5' C4 N1 C3 -118.8(6) ? C5 C4 N1 C3 -155.7(2) ? C5' C4 N1 C7 5.3(6) ? C5 C4 N1 C7 -31.6(3) ? C6 C7 N1 C3 144.2(2) ? C6 C7 N1 C4 17.9(3) ? O7 C1 P1 O1 67.66(13) ? C2 C1 P1 O1 -52.36(14) ? P2 C1 P1 O1 -179.67(9) y O7 C1 P1 O2 -168.62(11) ? C2 C1 P1 O2 71.36(14) ? P2 C1 P1 O2 -55.95(12) y O7 C1 P1 O3 -48.72(13) ? C2 C1 P1 O3 -168.73(12) ? P2 C1 P1 O3 63.95(11) y O7 C1 P2 O6 -177.27(10) ? C2 C1 P2 O6 -60.44(14) ? P1 C1 P2 O6 67.38(11) y O7 C1 P2 O5 59.27(12) ? C2 C1 P2 O5 176.10(12) ? P1 C1 P2 O5 -56.08(11) y O7 C1 P2 O4 -55.20(13) ? C2 C1 P2 O4 61.63(14) ? P1 C1 P2 O4 -170.55(9) y N1 C4 C5' C6 -25.8(9) ? C7 C6 C5' C4 35.9(9) ?