#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012584.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_2012584 loop_ _publ_author_name 'Usman, Anwar' 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Poh, Bo-Long' 'Karalai, Chatchanok' _publ_section_title ; Piperazine-1,4-diium--2,4-dinitrophenolate--water (1/2/2) ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o136 _journal_page_last o138 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C4 H12 N2 2+ , 2C6 H3 N2 O5 - , 2H2 O' _chemical_formula_moiety 'C4 H12 N2 2+ , 2C6 H3 N2 O5 - , 2H2 O' _chemical_formula_sum 'C16 H22 N6 O12' _chemical_formula_weight 490.40 _chemical_name_systematic ; Piperazine-1,4-diium--2,4-dinitrophenolate--water (1/2/2) ; _chemical_temperature_decomposition 515 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 99.6460(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 12.1140(6) _cell_length_b 12.9702(6) _cell_length_c 6.5813(3) _cell_measurement_reflns_used 4041 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 3.14 _cell_volume 1019.44(8) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 183(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .966 _diffrn_measured_fraction_theta_max .966 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .065 _diffrn_reflns_av_sigmaI/netI .103 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5886 _diffrn_reflns_theta_full 28.30 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_min 3.14 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .138 _exptl_absorpt_correction_T_max .981 _exptl_absorpt_correction_T_min .960 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 512 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .14 _refine_diff_density_max .48 _refine_diff_density_min -.40 _refine_ls_extinction_coef .067(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXTL (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref .915 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 2453 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .915 _refine_ls_R_factor_all .070 _refine_ls_R_factor_gt .052 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0301P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .115 _refine_ls_wR_factor_ref .120 _reflns_number_gt 1725 _reflns_number_total 2453 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ln1130.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been '515K (decompose)'. The value '515K (decompose)' was changed to '515'. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been '515K (decompose)'. The value '515K (decompose)' was changed to '515'. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 2012584 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' 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 O1 .69486(11) .52605(10) .2104(2) .0201(3) Uani d . 1 . . O O2 .65629(11) .72209(11) .3258(3) .0261(4) Uani d . 1 . . O O3 .78449(12) .83264(10) .2887(3) .0274(4) Uani d . 1 . . O O4 1.16477(12) .73032(11) .4446(3) .0293(4) Uani d . 1 . . O O5 1.21241(11) .58732(12) .3116(3) .0322(4) Uani d . 1 . . O N2 .75300(12) .74294(11) .3032(3) .0159(4) Uani d . 1 . . N N3 1.14065(13) .64615(12) .3570(3) .0196(4) Uani d . 1 . . N C3 .79589(15) .55678(14) .2386(3) .0145(4) Uani d . 1 . . C C8 .83223(14) .66063(13) .2916(3) .0135(4) Uani d . 1 . . C C7 .94390(15) .68943(14) .3278(3) .0144(4) Uani d . 1 . . C C6 1.02475(14) .61690(14) .3082(3) .0145(4) Uani d . 1 . . C C5 .99577(15) .51553(14) .2483(3) .0170(4) Uani d . 1 . . C C4 .88576(15) .48688(15) .2156(3) .0175(4) Uani d . 1 . . C H7 .9620(18) .7579(16) .367(3) .020(6) Uiso d . 1 . . H H5 1.057(2) .4637(17) .235(4) .030(6) Uiso d . 1 . . H H4 .8650(18) .4150(16) .176(3) .020(5) Uiso d . 1 . . H N1 .48980(13) .56797(12) .3262(3) .0151(4) Uani d . 1 . . N C2 .48356(15) .60859(14) .5364(3) .0156(4) Uani d . 1 . . C C1 .44851(15) .45924(14) .3032(3) .0161(4) Uani d . 1 . . C H2A .5094(17) .6810(16) .534(3) .018(5) Uiso d . 1 . . H H2B .4035(18) .6062(16) .551(3) .021(5) Uiso d . 1 . . H H2N .4486(19) .6086(16) .219(4) .026(6) Uiso d . 1 . . H H1N .568(2) .5718(19) .299(4) .042(7) Uiso d . 1 . . H H1A .456(2) .4356(17) .171(4) .027(6) Uiso d . 1 . . H H1B .3695(17) .4632(14) .315(3) .013(5) Uiso d . 1 . . H H2W .675(3) .304(3) .020(5) .067(11) Uiso d . 1 . . H H1W .657(2) .400(2) .089(4) .049(8) Uiso d . 1 . . H O1W .62747(12) .34292(12) .0291(2) .0205(3) Uani d . 1 . . O 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 O1 .0133(6) .0191(7) .0293(9) -.0041(5) .0078(6) -.0049(6) O2 .0163(7) .0216(8) .0441(10) .0023(6) .0155(6) .0040(7) O3 .0223(7) .0102(7) .0507(11) -.0002(5) .0085(7) .0006(6) O4 .0183(7) .0238(8) .0452(10) -.0071(6) .0037(6) -.0062(7) O5 .0127(7) .0331(9) .0519(11) .0055(6) .0087(7) -.0037(8) N2 .0142(8) .0142(8) .0201(9) .0015(6) .0052(6) .0010(6) N3 .0140(7) .0198(8) .0255(9) -.0006(6) .0043(6) .0041(7) C3 .0138(8) .0156(9) .0151(9) -.0011(7) .0056(7) .0000(7) C8 .0138(8) .0119(9) .0158(9) .0026(7) .0058(7) .0009(7) C7 .0160(9) .0122(9) .0158(10) -.0003(7) .0048(7) .0015(7) C6 .0102(8) .0162(9) .0180(10) -.0001(7) .0046(7) .0021(7) C5 .0160(9) .0159(9) .0200(10) .0021(7) .0057(7) .0013(8) C4 .0180(9) .0133(9) .0222(11) -.0005(7) .0065(8) -.0035(8) N1 .0126(7) .0129(8) .0208(9) -.0006(6) .0051(6) .0014(7) C2 .0146(9) .0115(9) .0223(10) -.0005(7) .0075(7) -.0020(8) C1 .0133(9) .0135(9) .0219(11) -.0021(7) .0041(7) -.0023(8) O1W .0158(7) .0167(7) .0288(9) .0015(6) .0027(6) -.0037(6) 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 O1 C3 . 1.271(2) yes O2 N2 . 1.235(2) yes O3 N2 . 1.2330(19) yes O4 N3 . 1.246(2) yes O5 N3 . 1.230(2) yes N2 C8 . 1.446(2) yes N3 C6 . 1.438(2) yes C3 C4 . 1.444(3) yes C3 C8 . 1.442(2) yes C8 C7 . 1.385(2) ? C4 C5 . 1.365(3) yes C6 C7 . 1.380(2) yes C7 H7 . .94(2) ? C6 C5 . 1.400(3) ? C5 H5 . 1.01(2) ? C4 H4 . .99(2) ? N1 C2 . 1.494(2) ? N1 C1 . 1.496(2) ? N1 H2N . .95(2) ? N1 H1N . .99(3) ? C2 C1 3_666 1.508(3) ? C2 H2A . .99(2) ? C2 H2B . .99(2) ? C1 C2 3_666 1.508(3) ? C1 H1A . .94(2) ? C1 H1B . .98(2) ? O1W H2W . .77(3) ? O1W H1W . .88(3) ? 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 O3 N2 O2 . . 121.85(15) O3 N2 C8 . . 118.42(15) O2 N2 C8 . . 119.73(15) O5 N3 O4 . . 122.35(16) O5 N3 C6 . . 119.04(16) O4 N3 C6 . . 118.61(16) O1 C3 C8 . . 125.17(17) O1 C3 C4 . . 120.81(16) C8 C3 C4 . . 114.01(16) C7 C8 C3 . . 122.92(16) C7 C8 N2 . . 115.44(15) C3 C8 N2 . . 121.60(15) C6 C7 C8 . . 119.23(17) C6 C7 H7 . . 122.2(13) C8 C7 H7 . . 118.5(13) C7 C6 C5 . . 121.20(16) C7 C6 N3 . . 118.77(16) C5 C6 N3 . . 120.00(16) C4 C5 C6 . . 119.46(17) C4 C5 H5 . . 120.7(13) C6 C5 H5 . . 119.8(13) C5 C4 C3 . . 123.07(17) C5 C4 H4 . . 119.8(12) C3 C4 H4 . . 117.2(12) C2 N1 C1 . . 110.98(15) C2 N1 H2N . . 113.0(13) C1 N1 H2N . . 108.8(13) C2 N1 H1N . . 110.4(15) C1 N1 H1N . . 110.0(14) H2N N1 H1N . . 104(2) N1 C2 C1 . 3_666 109.64(15) N1 C2 H2A . . 104.6(13) C1 C2 H2A 3_666 . 115.4(12) N1 C2 H2B . . 106.2(13) C1 C2 H2B 3_666 . 110.1(12) H2A C2 H2B . . 110.4(17) N1 C1 C2 . 3_666 110.21(15) N1 C1 H1A . . 108.4(14) C2 C1 H1A 3_666 . 109.3(14) N1 C1 H1B . . 104.9(11) C2 C1 H1B 3_666 . 113.7(12) H1A C1 H1B . . 110.0(18) H2W O1W H1W . . 109(3) 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 H1N O1 1_555 .99(2) 1.83(2) 2.772(2) 156(2) yes N1 H1N O2 1_555 .99(2) 2.22(2) 2.840(2) 119(2) yes N1 H2N O1W 3_665 .95(2) 1.85(3) 2.776(2) 165(2) yes O1W H1W O1 1_555 .89(3) 1.84(3) 2.721(2) 171(2) yes O1W H2W O4 2_745 .78(4) 2.14(4) 2.890(2) 162(4) yes C1 H1B O5 1_455 .97(2) 2.49(2) 3.316(2) 142.0(10) yes C1 H1B O3 2_645 .97(2) 2.53(2) 3.234(2) 129.0(10) yes C2 H2A O2 1_555 .99(2) 2.48(2) 3.072(2) 118(2) yes C2 H2B O5 1_455 .99(2) 2.58(2) 3.380(2) 137(2) yes C4 H4 O4 2_745 .99(2) 2.53(2) 3.513(2) 173(2) yes C5 H5 O3 2_745 1.02(2) 2.59(2) 3.604(2) 178(2) yes 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_4 _geom_torsion O1 C3 C8 C7 . 177.66(19) C4 C3 C8 C7 . -3.2(3) O1 C3 C8 N2 . -4.6(3) C4 C3 C8 N2 . 174.52(17) O3 N2 C8 C7 . 18.9(2) O2 N2 C8 C7 . -161.57(18) O3 N2 C8 C3 . -159.02(18) O2 N2 C8 C3 . 20.5(3) C3 C8 C7 C6 . 1.5(3) N2 C8 C7 C6 . -176.33(16) C8 C7 C6 C5 . 1.4(3) C8 C7 C6 N3 . -176.64(17) O5 N3 C6 C7 . -169.44(18) O4 N3 C6 C7 . 10.8(3) O5 N3 C6 C5 . 12.5(3) O4 N3 C6 C5 . -167.27(18) C7 C6 C5 C4 . -2.3(3) N3 C6 C5 C4 . 175.67(19) C6 C5 C4 C3 . .4(3) O1 C3 C4 C5 . -178.60(19) C8 C3 C4 C5 . 2.2(3) C1 N1 C2 C1 3_666 58.0(2) C2 N1 C1 C2 3_666 -58.3(2) _cod_database_fobs_code 2012584 _journal_paper_doi 10.1107/S0108270101021667