#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/33/2013328.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_2013328 loop_ _publ_author_name 'Fern\'andez, Daniel' 'Vega, Daniel' 'Ellena, Javier A.' _publ_section_title ; Two members of the bisphosphonate class of drugs: a zwitterion and a molecular compound ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o289 _journal_page_last o292 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C3 H11 N O6 P2' _chemical_formula_moiety 'C3 H11 N O6 P2' _chemical_formula_sum 'C3 H11 N O6 P2' _chemical_formula_weight 219.07 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.666(3) _cell_length_b 12.937(5) _cell_length_c 5.714(3) _cell_measurement_reflns_used 20 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 10 _cell_volume 862.4(6) _computing_cell_refinement ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993) ; _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 ; 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 0.0646 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 4140 _diffrn_reflns_theta_full 27.52 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 3.15 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 300 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.499 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cubic _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.327 _refine_diff_density_min -0.237 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.3(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 1987 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_gt 0.0486 _refine_ls_shift/su_max 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0603P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1185 _reflns_number_gt 1608 _reflns_number_total 1987 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1606.cif _[local]_cod_data_source_block I _cod_database_code 2013328 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, 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 0.3046(3) 0.1974(3) 0.2458(6) 0.0194(7) Uani d . 1 . . C C2 0.3630(4) 0.3046(3) 0.2556(8) 0.0294(9) Uani d . 1 . . C H4 0.4358 0.2965 0.3356 0.038 Uiso calc R 1 . . H H5 0.3799 0.3256 0.0963 0.038 Uiso calc R 1 . . H C3 0.2981(5) 0.3927(4) 0.3736(12) 0.0602(17) Uani d . 1 . . C H6 0.3455 0.4534 0.3767 0.078 Uiso calc R 1 . . H H7 0.2788 0.3731 0.5308 0.078 Uiso calc R 1 . . H H8 0.2292 0.407 0.2876 0.078 Uiso calc R 1 . . H N1 0.2784(3) 0.1605(3) 0.4907(5) 0.0201(7) Uani d . 1 . . N H1 0.2386 0.2088 0.5662 0.026 Uiso calc R 1 . . H H2 0.3437 0.1485 0.5666 0.026 Uiso calc R 1 . . H H3 0.2375 0.1025 0.4837 0.026 Uiso calc R 1 . . H O1 0.3562(2) -0.0034(2) 0.1576(5) 0.0266(6) Uani d . 1 . . O O2 0.4278(2) 0.1353(2) -0.1309(5) 0.0251(6) Uani d . 1 . . O O3 0.5133(2) 0.1115(2) 0.2768(5) 0.0270(6) Uani d D 1 . . O H9 0.563(3) 0.154(3) 0.249(9) 0.041 Uiso d D 1 . . H O4 0.0868(3) 0.2492(3) 0.2775(5) 0.0356(8) Uani d D 1 . . O H10 0.031(4) 0.284(4) 0.223(9) 0.053 Uiso d D 1 . . H O5 0.1255(3) 0.0911(3) 0.0553(6) 0.0342(7) Uani d D 1 . . O H11 0.133(5) 0.062(4) -0.075(6) 0.051 Uiso d D 1 . . H O6 0.1756(2) 0.2640(2) -0.1304(5) 0.0285(7) Uani d . 1 . . O P1 0.40511(8) 0.10223(7) 0.11730(16) 0.0190(2) Uani d . 1 . . P P2 0.16606(8) 0.20277(8) 0.09051(18) 0.0224(2) Uani d . 1 . . P 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 0.0202(17) 0.0254(19) 0.0125(16) -0.0028(15) 0.0000(14) -0.0003(16) C2 0.032(2) 0.0248(19) 0.031(2) -0.0083(17) 0.0041(18) -0.0011(19) C3 0.067(3) 0.031(2) 0.083(5) -0.006(2) 0.031(4) -0.015(3) N1 0.0203(16) 0.0268(17) 0.0134(15) 0.0002(14) 0.0002(13) -0.0007(13) O1 0.0281(14) 0.0252(14) 0.0265(15) -0.0021(12) -0.0025(12) 0.0005(12) O2 0.0222(13) 0.0367(15) 0.0165(14) -0.0040(11) -0.0007(12) 0.0020(11) O3 0.0192(14) 0.0362(16) 0.0256(15) -0.0051(12) -0.0039(12) 0.0035(13) O4 0.0328(16) 0.056(2) 0.0181(15) 0.0182(16) 0.0056(13) 0.0035(14) O5 0.0347(16) 0.0401(18) 0.0277(16) -0.0084(14) -0.0068(14) 0.0006(14) O6 0.0297(15) 0.0386(16) 0.0173(14) 0.0121(12) 0.0013(12) 0.0040(12) P1 0.0175(4) 0.0234(4) 0.0162(4) -0.0005(4) 0.0006(4) 0.0006(4) P2 0.0209(5) 0.0313(5) 0.0151(4) 0.0045(4) 0.0006(4) 0.0011(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C2 C3 . 1.526(7) ? C2 H4 . 0.97 ? C2 H5 . 0.97 ? C3 H6 . 0.96 ? C3 H7 . 0.96 ? C3 H8 . 0.96 ? N1 H1 . 0.89 ? N1 H2 . 0.89 ? N1 H3 . 0.89 ? O1 P1 . 1.498(3) y O2 P1 . 1.505(3) y O3 P1 . 1.561(3) y C1 P1 . 1.852(4) y O3 H9 . 0.82(3) ? O4 P2 . 1.536(3) y O4 H10 . 0.85(3) ? O5 P2 . 1.533(3) y O5 H11 . 0.84(3) ? O6 P2 . 1.494(3) y C1 C2 . 1.546(5) ? C1 P2 . 1.845(4) y C1 N1 . 1.510(5) y 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 N1 C1 C2 109.8(3) ? N1 C1 P2 106.3(2) ? C2 C1 P2 111.7(3) ? N1 C1 P1 106.6(2) ? C2 C1 P1 109.4(3) ? P1 C1 P2 112.89(19) y C1 C2 C3 117.9(4) y C3 C2 H4 107.8 ? C1 C2 H4 107.8 ? C3 C2 H5 107.8 ? C1 C2 H5 107.8 ? H4 C2 H5 107.2 ? C2 C3 H6 109.5 ? C2 C3 H7 109.5 ? H6 C3 H7 109.5 ? C2 C3 H8 109.5 ? H6 C3 H8 109.5 ? H7 C3 H8 109.5 ? C1 N1 H1 109.5 ? C1 N1 H2 109.5 ? H1 N1 H2 109.5 ? C1 N1 H3 109.5 ? H1 N1 H3 109.5 ? H2 N1 H3 109.5 ? P1 O3 H9 121(4) ? P2 O4 H10 114(4) ? P2 O5 H11 121(4) ? O1 P1 O2 118.11(16) y O1 P1 O3 106.74(16) y O2 P1 O3 112.71(16) y O1 P1 C1 107.72(17) ? O2 P1 C1 107.21(17) ? O3 P1 C1 103.24(16) ? O4 P2 O5 105.90(18) y O4 P2 O6 115.17(17) y O5 P2 O6 114.29(18) y O6 P2 C1 111.16(17) ? O5 P2 C1 107.32(18) ? O4 P2 C1 102.01(18) ? 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 N1 H1 O6 1_556 0.89 2.01 2.814(4) 149 N1 H2 O2 1_556 0.89 1.99 2.796(4) 149 N1 H3 O1 2_555 0.89 1.96 2.740(4) 146 O3 H9 O6 3_555 0.82(3) 1.82(3) 2.623(4) 169(5) O4 H10 O2 3_455 0.85(3) 1.68(3) 2.524(4) 173(6) O5 H11 O1 2_554 0.84(3) 1.71(3) 2.549(4) 179(6) 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 N1 C1 C2 C3 -58.6(5) ? P2 C1 C2 C3 59.0(5) ? P1 C1 C2 C3 -175.3(4) ? N1 C1 P1 O1 49.3(3) ? C2 C1 P1 O1 168.0(3) ? O1 P1 C1 P2 -67.0(2) y N1 C1 P1 O2 177.4(2) ? C2 C1 P1 O2 -63.9(3) ? O2 P1 C1 P2 61.1(2) y N1 C1 P1 O3 -63.4(3) ? C2 C1 P1 O3 55.3(3) ? O3 P1 C1 P2 -179.66(19) y N1 C1 P2 O6 164.9(2) ? C2 C1 P2 O6 45.2(3) ? O4 P2 C1 P1 158.2(2) y O5 P2 C1 P1 47.1(3) y O6 P2 C1 P1 -78.6(2) y N1 C1 P2 O5 -69.4(3) ? C2 C1 P2 O5 170.8(3) ? N1 C1 P2 O4 41.7(3) ? C2 C1 P2 O4 -78.1(3) ? _cod_database_fobs_code 2013328