#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012458.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_2012458 loop_ _publ_author_name 'Farrell, Dorcas M. M.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _publ_section_title ; A structural hierarchy in the hydrogen-bonded adduct N,N'-dimethylpiperazine--tartaric acid--water (1/2/2): an N-component N-dimensional structure (N~= 3) with substructures having N = 1 and 2 ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o6 _journal_page_last o8 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C6 H16 N2 2+, 2C4 H5 O6 1-, 2H2 O' _chemical_formula_moiety 'C6 H16 N2 2+, 2C4 H5 O6 1-, 2H2 O' _chemical_formula_sum 'C14 H30 N2 O14' _chemical_formula_weight 450.40 _chemical_name_systematic ; N,N'-Dimethylpiperazine--tartaric acid--water (1/2/2) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 96.406(2) _cell_angle_beta 106.359(2) _cell_angle_gamma 90.430(3) _cell_formula_units_Z 1 _cell_length_a 7.2907(3) _cell_length_b 8.3423(4) _cell_length_c 8.4324(4) _cell_measurement_reflns_used 2102 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 2.91 _cell_volume 488.63(4) _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, 2001)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(12) _diffrn_measured_fraction_theta_full .994 _diffrn_measured_fraction_theta_max .994 _diffrn_measurement_device_type KappaCCD _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 .71073 _diffrn_reflns_av_R_equivalents .049 _diffrn_reflns_av_sigmaI/netI .0549 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6667 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.91 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .138 _exptl_absorpt_correction_T_max .9796 _exptl_absorpt_correction_T_min .9533 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 240 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .15 _refine_diff_density_max .288 _refine_diff_density_min -.236 _refine_ls_extinction_coef .035(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2237 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all .0611 _refine_ls_R_factor_gt .0400 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.0973P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .0974 _refine_ls_wR_factor_ref .1087 _reflns_number_gt 1691 _reflns_number_total 2237 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1517.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012458 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_type_symbol N1 .32857(18) .40117(16) .41205(17) .0199(3) Uani d . 1 N C11 .3260(2) .5339(2) .5462(2) .0229(4) Uani d . 1 C C12 .5211(2) .5634(2) .6709(2) .0231(4) Uani d . 1 C C13 .1367(2) .3777(2) .2865(2) .0313(4) Uani d . 1 C O1 -.06654(15) .01311(13) .77621(14) .0204(3) Uani d . 1 O O2 -.02032(16) .27533(14) .87855(15) .0250(3) Uani d . 1 O O3 .59478(15) -.00246(14) .78062(14) .0207(3) Uani d . 1 O O4 .53434(15) .17035(13) .58960(14) .0200(3) Uani d . 1 O O5 .34509(15) .28538(14) .88812(15) .0259(3) Uani d . 1 O O6 .15410(15) .14631(13) .54491(13) .0207(3) Uani d . 1 O C1 .0353(2) .14454(19) .83062(19) .0178(3) Uani d . 1 C C2 .2476(2) .13263(19) .83847(19) .0183(3) Uani d . 1 C C3 .2709(2) .06235(19) .67021(19) .0171(3) Uani d . 1 C C4 .4815(2) .08143(18) .67629(19) .0172(3) Uani d . 1 C O7 .72788(18) .38219(16) 1.06172(17) .0308(3) Uani d . 1 O H1 .3574 .3061 .4602 .024 Uiso calc R 1 H H11A .2318 .5047 .6040 .027 Uiso calc R 1 H H11B .2856 .6342 .4958 .027 Uiso calc R 1 H H12A .5169 .6557 .7544 .028 Uiso calc R 1 H H12B .5552 .4670 .7301 .028 Uiso calc R 1 H H13A .1038 .4772 .2349 .047 Uiso calc R 1 H H13B .0404 .3514 .3415 .047 Uiso calc R 1 H H13C .1400 .2892 .2007 .047 Uiso calc R 1 H H3 .7076 .0115 .7768 .031 Uiso calc R 1 H H5 .2662 .3567 .8955 .039 Uiso calc R 1 H H6 .1245 .0864 .4538 .031 Uiso calc R 1 H H2 .3072 .0588 .9227 .022 Uiso calc R 1 H H3A .2305 -.0548 .6480 .021 Uiso calc R 1 H H71 .618(3) .338(3) 1.011(3) .042(6) Uiso d . 1 H H72 .803(4) .337(3) 1.004(3) .059(7) 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 N1 .0183(6) .0208(7) .0194(7) -.0022(5) .0023(5) .0049(5) C11 .0217(8) .0240(8) .0253(9) .0008(7) .0105(7) .0031(7) C12 .0290(9) .0230(8) .0186(8) -.0015(7) .0091(7) .0025(7) C13 .0253(9) .0295(9) .0314(10) -.0039(7) -.0070(8) .0103(8) O1 .0152(5) .0226(6) .0241(6) .0000(4) .0071(5) .0025(5) O2 .0210(6) .0243(6) .0309(7) .0022(5) .0107(5) -.0002(5) O3 .0129(5) .0286(6) .0233(6) .0026(4) .0069(5) .0093(5) O4 .0184(5) .0205(6) .0234(6) .0000(4) .0085(5) .0055(5) O5 .0154(5) .0255(6) .0335(7) -.0026(5) .0065(5) -.0091(5) O6 .0179(5) .0257(6) .0166(6) .0009(5) .0021(5) .0023(5) C1 .0149(7) .0241(8) .0151(8) .0019(6) .0046(6) .0040(6) C2 .0143(7) .0224(8) .0176(8) -.0002(6) .0041(6) .0009(6) C3 .0151(7) .0191(7) .0178(8) .0004(6) .0050(6) .0038(6) C4 .0174(8) .0175(7) .0168(8) .0008(6) .0056(6) -.0003(6) O7 .0181(6) .0394(8) .0310(7) -.0009(6) .0055(6) -.0084(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C13 N1 C11 . . 110.46(13) no C13 N1 C12 . 2_666 110.22(13) no C11 N1 C12 . 2_666 110.83(12) no C13 N1 H1 . . 108.4 no C11 N1 H1 . . 108.4 no C12 N1 H1 2_666 . 108.4 no N1 C11 C12 . . 111.15(13) no N1 C11 H11A . . 109.4 no C12 C11 H11A . . 109.4 no N1 C11 H11B . . 109.4 no C12 C11 H11B . . 109.4 no H11A C11 H11B . . 108.0 no N1 C12 C11 2_666 . 111.50(13) no N1 C12 H12A 2_666 . 109.3 no C11 C12 H12A . . 109.3 no N1 C12 H12B 2_666 . 109.3 no C11 C12 H12B . . 109.3 no H12A C12 H12B . . 108.0 no N1 C13 H13A . . 109.5 no N1 C13 H13B . . 109.5 no H13A C13 H13B . . 109.5 no N1 C13 H13C . . 109.5 no H13A C13 H13C . . 109.5 no H13B C13 H13C . . 109.5 no C4 O3 H3 . . 109.5 no C2 O5 H5 . . 109.5 no C3 O6 H6 . . 109.5 no O2 C1 O1 . . 126.46(14) no O2 C1 C2 . . 118.23(14) no O1 C1 C2 . . 115.30(13) no O5 C2 C3 . . 109.60(12) no O5 C2 C1 . . 111.22(12) no C3 C2 C1 . . 110.92(12) no O5 C2 H2 . . 108.3 no C3 C2 H2 . . 108.3 no C1 C2 H2 . . 108.3 no O6 C3 C2 . . 108.65(12) no O6 C3 C4 . . 110.96(12) no C2 C3 C4 . . 108.48(12) no O6 C3 H3A . . 109.6 no C2 C3 H3A . . 109.6 no C4 C3 H3A . . 109.6 no O4 C4 O3 . . 124.49(13) no O4 C4 C3 . . 121.56(14) no O3 C4 C3 . . 113.95(13) no H71 O7 H72 . . 103(2) 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 C13 . 1.494(2) no N1 C11 . 1.496(2) no N1 C12 2_666 1.500(2) no N1 H1 . .93 no C11 C12 . 1.511(2) no C11 H11A . .99 no C11 H11B . .99 no C12 N1 2_666 1.500(2) no C12 H12A . .99 no C12 H12B . .99 no C13 H13A . .98 no C13 H13B . .98 no C13 H13C . .98 no O1 C1 . 1.2836(19) no O2 C1 . 1.2325(19) no O3 C4 . 1.2972(19) no O3 H3 . .84 no O4 C4 . 1.2281(18) no O5 C2 . 1.4155(18) no O5 H5 . .84 no O6 C3 . 1.4139(19) no O6 H6 . .84 no C1 C2 . 1.535(2) no C2 C3 . 1.529(2) no C2 H2 . 1.00 no C3 C4 . 1.528(2) no C3 H3A . 1.00 no O7 H71 . .86(2) no O7 H72 . .89(3) 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 O4 . .93 1.91 2.761(2) 151 y N1 H1 O6 . .93 2.29 2.947(2) 127 y O3 H3 O1 1_655 .84 1.65 2.483(2) 172 y O5 H5 O2 . .84 2.15 2.643(2) 117 y O5 H5 O7 2_667 .84 2.17 2.836(2) 137 y O6 H6 O1 2_556 .84 1.95 2.778(2) 168 y O7 H71 O5 . .86(2) 1.99(2) 2.826(2) 167(2) y O7 H72 O2 1_655 .89(3) 1.92(3) 2.805(2) 171(2) 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C13 N1 C11 C12 . . -177.87(13) no C12 N1 C11 C12 2_666 . -55.42(19) no N1 C11 C12 N1 . 2_666 55.80(19) no O2 C1 C2 O5 . . -5.5(2) no O1 C1 C2 O5 . . 175.70(13) no O2 C1 C2 C3 . . -127.74(15) no O1 C1 C2 C3 . . 53.45(18) no O5 C2 C3 O6 . . -73.96(15) no C1 C2 C3 O6 . . 49.23(16) no O5 C2 C3 C4 . . 46.77(17) no C1 C2 C3 C4 . . 169.96(12) no O6 C3 C4 O4 . . 5.4(2) no C2 C3 C4 O4 . . -113.93(16) no O6 C3 C4 O3 . . -175.25(12) no C2 C3 C4 O3 . . 65.47(17) no