#------------------------------------------------------------------------------ #$Date: 2015-04-02 14:22:18 +0300 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/64/2006418.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_2006418 loop_ _publ_author_name 'Paix\~ao, J. A.' 'Matos Beja, A.' 'Ramos Silva, M.' 'de Matos Gomes, E.' 'Mart\'in-Gil, J.' 'Mart\'in-Gil, F.J.' _publ_section_title ; N,N'-Diphenylguanidinium Hydrogenselenite Monohydrate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1113 _journal_page_last 1115 _journal_paper_doi 10.1107/S0108270197004472 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C13 H14 N3 1+,H Se O3 1-, H2 O' _chemical_formula_structural '(C13 H14 N3) (H Se O3) (H2 O)' _chemical_formula_sum 'C13 H17 N3 O4 Se' _chemical_formula_weight 358.26 _chemical_name_systematic ; N,N'-Diphenylguanidinium hydrogenselenite monohydrate ; _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 SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 93.750(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.3600(10) _cell_length_b 19.272(2) _cell_length_c 12.604(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15.8 _cell_measurement_theta_min 9.8 _cell_volume 1541.6(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf Nonius, 1989)' _computing_data_reduction 'SDP-Plus (Frenz, 1985)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL93 _computing_structure_refinement SHELXL93 _computing_structure_solution 'MULTAN11/82 (Main et al., 1982)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method 'profile data from \w--2\q scans' _diffrn_radiation_monochromator 'equatorial mounted graphite' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0904 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 6572 _diffrn_reflns_theta_max 35.0 _diffrn_reflns_theta_min 3.24 _diffrn_standards_decay_% 0.3 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.454 _exptl_absorpt_correction_T_max 0.78 _exptl_absorpt_correction_T_min 0.56 _exptl_absorpt_correction_type '\y scan (North, Phillips & Mathews, 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _refine_diff_density_max .421 _refine_diff_density_min -.342 _refine_ls_extinction_coef 0.0048(6) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.060 _refine_ls_goodness_of_fit_obs 1.083 _refine_ls_hydrogen_treatment 'H atoms riding' _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 3157 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_restrained_S_obs 1.083 _refine_ls_R_factor_all 0.1156 _refine_ls_R_factor_obs .0305 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0194P)^2^+1.3453P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0813 _refine_ls_wR_factor_obs .0620 _reflns_number_observed 1844 _reflns_number_total 3157 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file na1285.cif _[local]_cod_data_source_block dpgse _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0194P)^2^+1.3453P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0194P)^2^+1.3453P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2006418 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_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 Se .0335(2) .0413(2) .0262(2) -.0029(2) .00620(14) -.0069(2) O1 .0417(14) .0494(14) .0339(13) -.0149(11) .0144(11) -.0110(11) O2 .0270(12) .0486(14) .0376(13) -.0002(10) .0058(10) -.0023(10) O3 .054(2) .0375(13) .074(2) .0033(13) .0061(15) .0036(13) O4 .062(3) .068(2) .125(3) -.027(2) .023(3) -.019(2) N1 .0319(15) .042(2) .0240(13) -.0093(13) .0084(12) -.0062(12) N3 .036(2) .042(2) .0300(15) -.0126(14) .0158(13) -.0117(13) N2 .037(2) .046(2) .0296(14) -.0159(14) .0163(13) -.0102(13) C1 .026(2) .036(2) .028(2) .0020(14) .0079(15) -.0047(15) C2 .030(2) .033(2) .026(2) -.0005(15) .0090(15) -.0069(14) C3 .030(2) .035(2) .042(2) .002(2) .002(2) .000(2) C4 .033(2) .042(2) .067(3) -.006(2) .011(2) .002(2) C5 .059(3) .048(2) .055(2) -.013(2) .029(2) -.001(2) C6 .071(3) .048(2) .032(2) -.012(2) .010(2) .002(2) C7 .047(2) .047(2) .030(2) -.008(2) -.002(2) -.001(2) C8 .033(2) .035(2) .0237(15) -.0067(15) .0045(15) -.0005(13) C9 .044(2) .039(2) .034(2) .002(2) .004(2) -.001(2) C10 .077(3) .035(2) .040(2) -.003(2) .000(2) .000(2) C11 .074(3) .046(2) .043(2) -.026(2) .001(2) .006(2) C12 .043(2) .060(3) .042(2) -.018(2) .007(2) .011(2) C13 .041(2) .039(2) .035(2) -.004(2) .007(2) .005(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Se .19012(5) .14832(2) -.02029(2) .03346(13) Uani d . 1 . Se O1 .3487(3) .20738(12) .0357(2) .0411(6) Uani d . 1 . O O2 -.0422(3) .16349(11) .0289(2) .0376(6) Uani d . 1 . O O3 .2701(4) .07616(12) .0591(2) .0552(7) Uani d . 1 . O H18 .253(7) .0405(2) .0242(11) .083 Uiso calc R 1 . H O4 .6990(5) .0509(2) .0389(4) .0840(13) Uani d . 1 . O H16 .781(9) .075(3) .043(5) .126 Uiso d . 1 . H H17 .617(10) .056(4) .048(7) .126 Uiso d . 1 . H N1 -.0014(4) .19933(13) .2501(2) .0323(6) Uani d . 1 . N H1 -.0042(4) .19032(13) .1832(2) .048 Uiso calc R 1 . H N3 .2628(4) .27423(14) .2159(2) .0355(7) Uani d . 1 . N H2 .2684(4) .25177(14) .1572(2) .053 Uiso calc R 1 . H N2 .1421(4) .27042(14) .3851(2) .0370(7) Uani d . 1 . N H14 .2309(4) .30201(14) .4060(2) .056 Uiso calc R 1 . H H15 .0582(4) .25315(14) .4290(2) .056 Uiso calc R 1 . H C1 .1347(5) .2485(2) .2860(2) .0298(7) Uani d . 1 . C C2 -.1405(5) .1607(2) .3101(2) .0295(7) Uani d . 1 . C C3 -.3431(5) .1490(2) .2657(3) .0360(8) Uani d . 1 . C H3 -.3837(5) .1669(2) .1989(3) .054 Uiso calc R 1 . H C4 -.4840(6) .1110(2) .3206(3) .0473(10) Uani d . 1 . C H4 -.6191(6) .1030(2) .2904(3) .071 Uiso calc R 1 . H C5 -.4261(7) .0850(2) .4193(3) .0529(10) Uani d . 1 . C H5 -.5232(7) .0607(2) .4570(3) .079 Uiso calc R 1 . H C6 -.2242(6) .0949(2) .4626(3) .0501(10) Uani d . 1 . C H6 -.1845(6) .0762(2) .5289(3) .075 Uiso calc R 1 . H C7 -.0807(6) .1320(2) .4088(3) .0415(9) Uani d . 1 . C H7 .0560(6) .1380(2) .4383(3) .062 Uiso calc R 1 . H C8 .3906(5) .3343(2) .2274(2) .0305(7) Uani d . 1 . C C9 .3214(6) .3957(2) .2706(3) .0387(8) Uani d . 1 . C H9 .1887(6) .3980(2) .2973(3) .058 Uiso calc R 1 . H C10 .4509(7) .4532(2) .2738(3) .0508(10) Uani d . 1 . C H10 .4062(7) .4939(2) .3049(3) .076 Uiso calc R 1 . H C11 .6441(7) .4512(2) .2319(3) .0545(11) Uani d . 1 . C H11 .7292(7) .4905(2) .2338(3) .082 Uiso calc R 1 . H C12 .7113(6) .3910(2) .1871(3) .0482(10) Uani d . 1 . C H12 .8418(6) .3897(2) .1579(3) .072 Uiso calc R 1 . H C13 .5864(5) .3322(2) .1849(3) .0380(8) Uani d . 1 . C H13 .6335(5) .2914(2) .1552(3) .057 Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Se Se -.0929 2.2259 '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' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 O1 Se O2 104.62(11) yes O1 Se O3 98.94(12) yes O2 Se O3 99.02(12) yes Se O3 H18 109.47(9) no H16 O4 H17 126.(10) no C1 N1 C2 127.2(3) yes C1 N1 H1 116.4(2) no C2 N1 H1 116.4(2) no C1 N3 C8 127.4(3) yes C1 N3 H2 116.3(2) no C8 N3 H2 116.3(2) no C1 N2 H14 120.0(2) no C1 N2 H15 120.0(2) no H14 N2 H15 120.0 no N2 C1 N3 121.5(3) yes N2 C1 N1 121.9(3) yes N3 C1 N1 116.6(3) yes C3 C2 C7 119.2(3) no C3 C2 N1 117.8(3) yes C7 C2 N1 122.9(3) yes C4 C3 C2 120.0(3) no C4 C3 H3 120.0(2) no C2 C3 H3 120.0(2) no C5 C4 C3 120.4(3) no C5 C4 H4 119.8(2) no C3 C4 H4 119.8(2) no C4 C5 C6 119.9(3) no C4 C5 H5 120.1(2) no C6 C5 H5 120.1(2) no C7 C6 C5 120.7(3) no C7 C6 H6 119.7(2) no C5 C6 H6 119.7(2) no C6 C7 C2 119.8(3) no C6 C7 H7 120.1(2) no C2 C7 H7 120.1(2) no C9 C8 C13 119.6(3) no C9 C8 N3 122.9(3) yes C13 C8 N3 117.4(3) yes C10 C9 C8 119.5(3) no C10 C9 H9 120.2(2) no C8 C9 H9 120.2(2) no C11 C10 C9 121.0(4) no C11 C10 H10 119.5(2) no C9 C10 H10 119.5(2) no C10 C11 C12 119.6(3) no C10 C11 H11 120.2(2) no C12 C11 H11 120.2(2) no C11 C12 C13 120.5(3) no C11 C12 H12 119.7(2) no C13 C12 H12 119.7(2) no C12 C13 C8 119.8(3) no C12 C13 H13 120.1(2) no C8 C13 H13 120.1(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 Se O1 . 1.649(2) yes Se O2 . 1.665(2) yes Se O3 . 1.768(2) yes O3 H18 . .82 no O4 H16 . .69(6) no O4 H17 . .55(7) no N1 C1 . 1.342(4) yes N1 C2 . 1.413(4) yes N1 H1 . .86 no N3 C1 . 1.335(4) yes N3 C8 . 1.417(4) yes N3 H2 . .86 no N2 C1 . 1.317(4) yes N2 H14 . .86 no N2 H15 . .86 no C2 C3 . 1.389(4) no C2 C7 . 1.392(4) no C3 C4 . 1.378(5) no C3 H3 . .93 no C4 C5 . 1.370(5) no C4 H4 . .93 no C5 C6 . 1.375(5) no C5 H5 . .93 no C6 C7 . 1.373(5) no C6 H6 . .93 no C7 H7 . .93 no C8 C9 . 1.385(4) no C8 C13 . 1.388(5) no C9 C10 . 1.380(5) no C9 H9 . .93 no C10 C11 . 1.370(5) no C10 H10 . .93 no C11 C12 . 1.371(5) no C11 H11 . .93 no C12 C13 . 1.384(5) no C12 H12 . .93 no C13 H13 . .93 no 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 C8 N3 C1 N2 -12.8(5) no C8 N3 C1 N1 167.2(3) no C2 N1 C1 N2 -5.2(5) no C2 N1 C1 N3 174.8(3) no C1 N1 C2 C3 138.7(3) no C1 N1 C2 C7 -43.9(5) no C7 C2 C3 C4 1.8(5) no N1 C2 C3 C4 179.3(3) no C2 C3 C4 C5 0.5(5) no C3 C4 C5 C6 -2.1(6) no C4 C5 C6 C7 1.5(6) no C5 C6 C7 C2 0.7(5) no C3 C2 C7 C6 -2.3(5) no N1 C2 C7 C6 -179.7(3) no C1 N3 C8 C9 -42.0(5) no C1 N3 C8 C13 143.4(3) no C13 C8 C9 C10 -2.0(5) no N3 C8 C9 C10 -176.5(3) no C8 C9 C10 C11 2.0(5) no C9 C10 C11 C12 -0.7(5) no C10 C11 C12 C13 -0.7(5) no C11 C12 C13 C8 0.7(5) no C9 C8 C13 C12 0.6(5) no N3 C8 C13 C12 175.4(3) no