#------------------------------------------------------------------------------ #$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/29/2012900.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_2012900 loop_ _publ_author_name 'Bowes, Katharine F.' 'Ferguson, George' 'Glidewell, Christopher' 'Lough, Alan J.' _publ_section_title ; Self-assembled hydrogen-bonded bilayers in 1,4-diazabicyclo[2.2.2]octane--N-(phosphonomethyl)iminodiacetic acid--water (1/1/1.5) ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o467 _journal_page_last o469 _journal_paper_doi 10.1107/S0108270102010648 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C6 H14 N2 2+ , C5 H8 N O7 P 2- , 1.5H2 O' _chemical_formula_sum 'C11 H25 N3 O8.5 P' _chemical_formula_weight 366.31 _chemical_name_systematic ;1,4-diazoniabicyclo[2.2.2]octane-N-[(hydroxyphosphinato)methyl]iminiodiacetate -water (1/1/1.5 ; _space_group_IT_number 13 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yac' _symmetry_space_group_name_H-M 'P 1 2/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90.1130(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.1042(5) _cell_length_b 7.0560(3) _cell_length_c 16.4004(7) _cell_measurement_reflns_used 3693 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 2.89 _cell_volume 1632.15(11) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.066 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 12611 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.89 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 780 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.28 _refine_diff_density_min -0.35 _refine_ls_extinction_coef 0.0059(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 3693 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.055 _refine_ls_R_factor_gt 0.038 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0211P)^2^+0.6209P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.088 _refine_ls_wR_factor_ref 0.096 _reflns_number_gt 2841 _reflns_number_total 3693 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1565.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 2/n' _cod_original_formula_sum 'C11 H25 N3 O8.50 P' _cod_database_code 2012900 _cod_database_fobs_code 2012900 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, 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 P1 0.35479(3) 0.49736(6) 0.37217(3) 0.01558(13) Uani d . 1 . . P O1 0.09501(8) 0.57915(18) 0.62119(8) 0.0259(3) Uani d . 1 . . O O2 0.13606(8) 0.81849(17) 0.53953(7) 0.0229(3) Uani d . 1 . . O O3 0.40966(10) 1.15406(18) 0.56061(9) 0.0331(3) Uani d . 1 . . O O4 0.33110(9) 1.02862(17) 0.45382(8) 0.0253(3) Uani d . 1 . . O O5 0.28201(8) 0.33296(16) 0.38708(7) 0.0203(3) Uani d . 1 . . O O6 0.29982(8) 0.65875(16) 0.33464(7) 0.0182(3) Uani d . 1 . . O O7 0.44295(8) 0.43094(18) 0.33075(8) 0.0238(3) Uani d . 1 . . O N1 0.31306(9) 0.69209(19) 0.51503(8) 0.0147(3) Uani d . 1 . . N C1 0.15070(12) 0.6613(2) 0.57395(10) 0.0180(3) Uani d . 1 . . C C2 0.24396(11) 0.5615(2) 0.55575(11) 0.0180(3) Uani d . 1 . . C C3 0.36725(12) 1.0257(2) 0.52515(11) 0.0207(4) Uani d . 1 . . C C4 0.35272(12) 0.8392(2) 0.57152(10) 0.0187(4) Uani d . 1 . . C C5 0.39075(11) 0.5840(2) 0.47244(10) 0.0168(3) Uani d . 1 . . C N11 0.39288(9) 0.85447(19) 0.22781(8) 0.0162(3) Uani d . 1 . . N N21 0.50729(10) 1.0260(2) 0.13839(9) 0.0171(3) Uani d . 1 . . N C11 0.43010(12) 0.7211(2) 0.16478(10) 0.0183(4) Uani d . 1 . . C C12 0.47273(11) 0.9288(3) 0.27893(10) 0.0193(4) Uani d . 1 . . C C13 0.34342(11) 1.0169(2) 0.18775(11) 0.0180(4) Uani d . 1 . . C C21 0.51327(12) 0.8186(2) 0.12124(11) 0.0199(4) Uani d . 1 . . C C22 0.53196(12) 1.0631(3) 0.22592(10) 0.0199(4) Uani d . 1 . . C C23 0.40918(11) 1.0974(2) 0.12157(11) 0.0190(4) Uani d . 1 . . C O8 0.12465(9) 0.4676(2) 0.78408(8) 0.0299(3) Uani d . 1 . . O O9 0.2500 0.1535(3) 0.7500 0.0660(9) Uani d S 1 . . O H5 0.3098 0.2410 0.4092 0.030 Uiso calc R 1 . . H H1 0.2796 0.7567 0.4748 0.018 Uiso calc R 1 . . H H2A 0.2718 0.5139 0.6073 0.022 Uiso calc R 1 . . H H2B 0.2318 0.4511 0.5199 0.022 Uiso calc R 1 . . H H4A 0.4140 0.7951 0.5940 0.022 Uiso calc R 1 . . H H4B 0.3085 0.8597 0.6175 0.022 Uiso calc R 1 . . H H5A 0.4098 0.4749 0.5068 0.020 Uiso calc R 1 . . H H5B 0.4467 0.6675 0.4662 0.020 Uiso calc R 1 . . H H11 0.3502 0.7905 0.2611 0.019 Uiso calc R 1 . . H H21 0.5500 1.0899 0.1051 0.021 Uiso calc R 1 . . H H11A 0.3796 0.6896 0.1250 0.022 Uiso calc R 1 . . H H11B 0.4519 0.6023 0.1909 0.022 Uiso calc R 1 . . H H12A 0.5125 0.8226 0.2987 0.023 Uiso calc R 1 . . H H12B 0.4474 0.9976 0.3268 0.023 Uiso calc R 1 . . H H13A 0.3288 1.1160 0.2285 0.022 Uiso calc R 1 . . H H13B 0.2832 0.9734 0.1630 0.022 Uiso calc R 1 . . H H21A 0.5743 0.7674 0.1415 0.024 Uiso calc R 1 . . H H21B 0.5095 0.7955 0.0618 0.024 Uiso calc R 1 . . H H22A 0.5178 1.1965 0.2401 0.024 Uiso calc R 1 . . H H22B 0.6004 1.0402 0.2352 0.024 Uiso calc R 1 . . H H23A 0.3878 1.0552 0.0670 0.023 Uiso calc R 1 . . H H23B 0.4082 1.2376 0.1229 0.023 Uiso calc R 1 . . H H81 0.1248 0.5102 0.7362 0.063 Uiso d . 1 . . H H82 0.0716 0.4966 0.8036 0.063 Uiso d . 1 . . H H9 0.2138 0.2384 0.7679 0.063 Uiso d . 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 P1 0.0166(2) 0.0133(2) 0.0169(2) 0.00007(16) 0.00359(16) 0.00105(17) O1 0.0245(7) 0.0233(7) 0.0300(7) -0.0011(5) 0.0120(5) 0.0037(6) O2 0.0218(6) 0.0229(7) 0.0241(7) 0.0067(5) 0.0071(5) 0.0049(5) O3 0.0440(8) 0.0193(7) 0.0359(8) -0.0096(6) -0.0139(6) 0.0011(6) O4 0.0363(7) 0.0168(6) 0.0226(7) -0.0038(5) -0.0065(5) 0.0030(5) O5 0.0220(6) 0.0151(6) 0.0238(7) -0.0021(5) -0.0013(5) 0.0040(5) O6 0.0204(6) 0.0162(6) 0.0178(6) 0.0008(4) 0.0016(5) 0.0032(5) O7 0.0223(6) 0.0230(7) 0.0263(7) 0.0043(5) 0.0086(5) -0.0020(5) N1 0.0151(6) 0.0135(7) 0.0155(7) 0.0003(5) 0.0009(5) 0.0008(5) C1 0.0197(8) 0.0175(8) 0.0166(8) 0.0003(6) 0.0024(6) -0.0025(7) C2 0.0167(8) 0.0146(8) 0.0227(9) -0.0011(6) 0.0055(6) 0.0027(7) C3 0.0212(9) 0.0160(8) 0.0250(9) -0.0003(6) -0.0016(7) 0.0007(7) C4 0.0225(8) 0.0164(8) 0.0171(8) -0.0015(6) -0.0012(6) -0.0008(7) C5 0.0136(7) 0.0155(8) 0.0212(9) 0.0020(6) 0.0031(6) 0.0007(7) N11 0.0168(7) 0.0148(7) 0.0170(7) -0.0003(5) 0.0022(5) 0.0013(6) N21 0.0169(7) 0.0171(7) 0.0174(7) -0.0009(5) 0.0030(5) 0.0018(6) C11 0.0205(8) 0.0155(8) 0.0190(8) -0.0001(6) 0.0016(6) -0.0024(7) C12 0.0206(8) 0.0206(9) 0.0169(8) 0.0000(7) -0.0003(7) -0.0006(7) C13 0.0155(8) 0.0165(8) 0.0221(9) 0.0023(6) 0.0031(6) 0.0033(7) C21 0.0209(8) 0.0169(8) 0.0218(9) 0.0004(6) 0.0039(7) -0.0026(7) C22 0.0206(8) 0.0206(9) 0.0184(8) -0.0025(7) -0.0005(7) -0.0029(7) C23 0.0169(8) 0.0183(9) 0.0218(9) 0.0019(6) 0.0011(6) 0.0057(7) O8 0.0249(7) 0.0353(8) 0.0296(7) 0.0022(6) -0.0004(5) 0.0013(6) O9 0.0333(12) 0.0286(13) 0.136(3) 0.000 0.0113(14) 0.000 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' 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 P1 O6 118.63(7) no O7 P1 O5 112.61(7) no O6 P1 O5 106.61(7) no O7 P1 C5 106.55(7) no O6 P1 C5 104.87(7) no O5 P1 C5 106.73(7) no P1 O5 H5 109.5 no C4 N1 C2 113.11(13) no C4 N1 C5 111.47(12) no C2 N1 C5 111.65(12) no C4 N1 H1 106.7 no C2 N1 H1 106.7 no C5 N1 H1 106.7 no O1 C1 O2 125.72(15) no O1 C1 C2 116.90(15) no O2 C1 C2 117.38(14) no N1 C2 C1 111.44(13) no N1 C2 H2A 109.3 no C1 C2 H2A 109.3 no N1 C2 H2B 109.3 no C1 C2 H2B 109.3 no H2A C2 H2B 108.0 no O3 C3 O4 127.89(17) no O3 C3 C4 117.54(16) no O4 C3 C4 114.54(15) no N1 C4 C3 109.74(14) no N1 C4 H4A 109.7 no C3 C4 H4A 109.7 no N1 C4 H4B 109.7 no C3 C4 H4B 109.7 no H4A C4 H4B 108.2 no N1 C5 P1 112.69(11) no N1 C5 H5A 109.1 no P1 C5 H5A 109.1 no N1 C5 H5B 109.1 no P1 C5 H5B 109.1 no H5A C5 H5B 107.8 no C13 N11 C11 110.09(13) no C13 N11 C12 109.14(13) no C11 N11 C12 110.06(12) no C13 N11 H11 109.2 no C11 N11 H11 109.2 no C12 N11 H11 109.2 no C21 N21 C23 110.33(13) no C21 N21 C22 109.77(13) no C23 N21 C22 109.29(13) no C21 N21 H21 109.1 no C23 N21 H21 109.1 no C22 N21 H21 109.1 no N11 C11 C21 108.01(13) no N11 C11 H11A 110.1 no C21 C11 H11A 110.1 no N11 C11 H11B 110.1 no C21 C11 H11B 110.1 no H11A C11 H11B 108.4 no N11 C12 C22 107.98(13) no N11 C12 H12A 110.1 no C22 C12 H12A 110.1 no N11 C12 H12B 110.1 no C22 C12 H12B 110.1 no H12A C12 H12B 108.4 no N11 C13 C23 108.18(13) no N11 C13 H13A 110.1 no C23 C13 H13A 110.1 no N11 C13 H13B 110.1 no C23 C13 H13B 110.1 no H13A C13 H13B 108.4 no N21 C21 C11 107.92(13) no N21 C21 H21A 110.1 no C11 C21 H21A 110.1 no N21 C21 H21B 110.1 no C11 C21 H21B 110.1 no H21A C21 H21B 108.4 no N21 C22 C12 108.00(13) no N21 C22 H22A 110.1 no C12 C22 H22A 110.1 no N21 C22 H22B 110.1 no C12 C22 H22B 110.1 no H22A C22 H22B 108.4 no N21 C23 C13 107.71(13) no N21 C23 H23A 110.2 no C13 C23 H23A 110.2 no N21 C23 H23B 110.2 no C13 C23 H23B 110.2 no H23A C23 H23B 108.5 no H81 O8 H82 106 no 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 N1 C2 . 1.499(2) y N1 C4 . 1.499(2) y N1 C5 . 1.508(2) y N11 C11 . 1.494(2) y N11 C12 . 1.497(2) y N11 C13 . 1.493(2) y N21 C21 . 1.493(2) y N21 C22 . 1.499(2) y N21 C23 . 1.498(2) y P1 O5 . 1.5685(12) y P1 O6 . 1.5083(12) y P1 O7 . 1.4934(12) y P1 C5 . 1.8253(17) y C1 O1 . 1.247(2) y C1 O2 . 1.262(2) y C3 O3 . 1.231(2) y C3 O4 . 1.275(2) y O5 H5 . 0.84 no N1 H1 . 0.93 no C1 C2 . 1.522(2) no C2 H2A . 0.99 no C2 H2B . 0.99 no C3 C4 . 1.533(2) no C4 H4A . 0.99 no C4 H4B . 0.99 no C5 H5A . 0.99 no C5 H5B . 0.99 no N11 H11 . 0.93 no N21 H21 . 0.93 no C11 C21 . 1.537(2) no C11 H11A . 0.99 no C11 H11B . 0.99 no C12 C22 . 1.534(2) no C12 H12A . 0.99 no C12 H12B . 0.99 no C13 C23 . 1.538(2) no C13 H13A . 0.99 no C13 H13B . 0.99 no C21 H21A . 0.99 no C21 H21B . 0.99 no C22 H22A . 0.99 no C22 H22B . 0.99 no C23 H23A . 0.99 no C23 H23B . 0.99 no O8 H81 . 0.84 no O8 H82 . 0.84 no O9 H9 . 0.84 no 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 _geom_hbond_publ_flag N1 H1 O2 . 0.93 2.33 2.682(2) 102 y N1 H1 O4 . 0.93 2.08 2.591(2) 113 y N1 H1 O6 . 0.93 2.42 2.973(2) 118 y O5 H5 O4 1_545 0.84 1.69 2.507(2) 162 y N11 H11 O6 . 0.93 1.68 2.590(2) 165 y N21 H21 O1 4_675 0.93 2.43 3.062(2) 125 y N21 H21 O2 4_675 0.93 1.75 2.673(2) 173 y O8 H81 O1 . 0.84 1.99 2.815(2) 166 y O8 H82 O7 4_566 0.84 1.94 2.770(2) 171 y O9 H9 O8 . 0.84 2.07 2.891(2) 167 y 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 C4 N1 C2 C1 72.1(2) no C5 N1 C2 C1 -161.2(2) no O1 C1 C2 N1 -166.7(2) y O2 C1 C2 N1 14.0(2) no C2 N1 C4 C3 -144.34(13) no C5 N1 C4 C3 88.88(16) no O3 C3 C4 N1 -171.7(2) y O4 C3 C4 N1 9.7(2) no C4 N1 C5 P1 -150.9(2) no C2 N1 C5 P1 81.52(14) no O7 P1 C5 N1 168.3(2) y O6 P1 C5 N1 41.73(13) no O5 P1 C5 N1 -71.14(12) no C13 N11 C11 C21 70.5(2) no C12 N11 C11 C21 -49.8(2) no C13 N11 C12 C22 -50.6(2) no C11 N11 C12 C22 70.3(2) no C11 N11 C13 C23 -49.8(2) no C12 N11 C13 C23 71.1(2) no C23 N21 C21 C11 -49.7(2) no C22 N21 C21 C11 70.8(2) no N11 C11 C21 N21 -17.5(2) y C21 N21 C22 C12 -50.3(2) no C23 N21 C22 C12 70.9(2) no N11 C12 C22 N21 -16.9(2) y C21 N21 C23 C13 70.4(2) no C22 N21 C23 C13 -50.4(2) no N11 C13 C23 N21 -17.2(2) y