#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012020.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_2012020 loop_ _publ_author_name 'Steiner, Thomas' _publ_section_title ; The C---H···O hydrogen bond in (dicyanomethyl)ammonium p-toluenesulfonate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 775 _journal_page_last 776 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C3 H4 N3 + , C7 H7 O3 S - ' _chemical_formula_sum 'C10 H11 N3 O3 S' _chemical_formula_weight 253.28 _chemical_name_common 'aminomalononitrile p-toluenesulfonate' _chemical_name_systematic ; Ammonio-malononitrile p-toluenesulfonate ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 96.40(14) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.604(9) _cell_length_b 25.90(5) _cell_length_c 8.427(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.9 _cell_measurement_theta_min 8.2 _cell_volume 1216(4) _computing_cell_refinement 'STOE Diffractometer Software' _computing_data_collection 'STOE Diffractometer Software (Stoe & Cie, 1993)' _computing_data_reduction 'STOE Diffractometer Software' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type 'STOE for-circle diffractometer' _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 .0185 _diffrn_reflns_av_sigmaI/netI .0283 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3001 _diffrn_reflns_theta_full 27.03 _diffrn_reflns_theta_max 27.03 _diffrn_reflns_theta_min 2.56 _diffrn_standards_decay_% 3 _diffrn_standards_interval_time 90 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .267 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 528 _exptl_crystal_size_max .8 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .05 _refine_diff_density_max .447 _refine_diff_density_min -.389 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 171 _refine_ls_number_reflns 2660 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all .0604 _refine_ls_R_factor_gt .0451 _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^)+(0.0656P)^2^+0.4531P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1260 _reflns_number_gt 2162 _reflns_number_total 2660 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file de1169.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21 /n' _cod_database_code 2012020 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_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 S1 .74752(8) .190589(19) .62961(5) .03177(16) Uani d . 1 S O1 .7303(3) .22032(6) .77468(16) .0393(4) Uani d . 1 O O2 .5660(3) .20656(6) .50249(17) .0416(4) Uani d . 1 O O3 .9874(3) .19285(6) .58114(19) .0421(4) Uani d . 1 O C1 .6888(4) .12601(8) .6734(2) .0376(4) Uani d . 1 C C2 .4753(5) .10355(10) .6150(3) .0555(6) Uani d . 1 C H2 .3612 .1220 .5491 .067 Uiso calc R 1 H C3 .4331(6) .05303(12) .6559(4) .0701(8) Uani d . 1 C H3 .2887 .0377 .6162 .084 Uiso calc R 1 H C4 .5962(6) .02478(11) .7530(4) .0649(8) Uani d . 1 C C5 .8057(6) .04836(12) .8096(4) .0749(9) Uani d . 1 C H5 .9188 .0300 .8764 .090 Uiso calc R 1 H C6 .8552(5) .09854(11) .7707(3) .0585(7) Uani d . 1 C H6 1.0002 .1137 .8102 .070 Uiso calc R 1 H C7 .5440(8) -.03045(12) .7971(5) .1013(14) Uani d . 1 C H7A .4951 -.0314 .9027 .152 Uiso calc R 1 H H7B .6861 -.0510 .7942 .152 Uiso calc R 1 H H7C .4177 -.0440 .7224 .152 Uiso calc R 1 H N1 .7754(3) .23564(8) 1.2375(2) .0358(4) Uani d . 1 N H1A .705(5) .2282(10) 1.326(3) .043(6) Uiso d . 1 H H1B .694(5) .2636(11) 1.186(3) .048(7) Uiso d . 1 H H1C .932(5) .2464(10) 1.261(3) .057(8) Uiso d . 1 H N2 .3287(4) .17136(10) 1.0170(3) .0660(6) Uani d . 1 N N3 .9688(5) .11085(11) 1.2746(4) .0798(8) Uani d . 1 N C8 .7701(4) .19072(9) 1.1300(2) .0379(5) Uani d . 1 C H8 .856(4) .2001(9) 1.043(3) .040(6) Uiso d . 1 H C9 .5202(4) .17894(10) 1.0673(3) .0460(5) Uani d . 1 C C10 .8828(4) .14550(10) 1.2127(3) .0496(6) Uani d . 1 C 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 S1 .0255(3) .0428(3) .0273(3) -.00154(19) .00438(18) .00006(19) O1 .0380(8) .0492(9) .0310(7) .0038(6) .0044(6) -.0028(6) O2 .0335(7) .0597(9) .0309(7) -.0018(7) .0001(6) .0078(7) O3 .0287(7) .0521(9) .0473(9) -.0057(6) .0124(6) -.0074(7) C1 .0336(10) .0438(11) .0366(10) -.0024(9) .0093(8) -.0004(9) C2 .0423(13) .0523(14) .0703(17) -.0081(11) -.0010(12) -.0042(12) C3 .0586(16) .0594(17) .095(2) -.0210(14) .0188(16) -.0116(16) C4 .0734(19) .0470(14) .0802(19) -.0018(13) .0345(16) .0030(13) C5 .077(2) .0641(18) .084(2) .0066(16) .0080(17) .0273(16) C6 .0463(14) .0603(16) .0669(17) -.0037(12) -.0031(12) .0178(13) C7 .130(3) .0505(18) .134(4) -.009(2) .060(3) .005(2) N1 .0285(8) .0471(10) .0319(9) -.0029(8) .0032(7) .0056(8) N2 .0430(12) .0849(17) .0677(15) -.0143(12) -.0043(11) -.0044(13) N3 .0799(18) .0658(16) .091(2) .0199(14) -.0045(15) .0053(15) C8 .0293(10) .0544(13) .0305(10) -.0019(9) .0057(8) .0023(9) C9 .0399(12) .0563(14) .0413(12) -.0063(10) .0022(10) -.0003(10) C10 .0437(13) .0535(14) .0514(14) .0027(11) .0043(11) -.0025(11) 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' S S .1246 .1234 '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 O3 S1 O2 112.08(14) ? O3 S1 O1 111.42(14) ? O2 S1 O1 111.22(14) ? O3 S1 C1 107.45(10) ? O2 S1 C1 107.14(11) ? O1 S1 C1 107.24(14) ? C6 C1 C2 120.2(3) ? C6 C1 S1 119.4(2) ? C2 C1 S1 120.40(19) ? C1 C2 C3 118.6(3) ? C1 C2 H2 120.7 ? C3 C2 H2 120.7 ? C4 C3 C2 122.3(3) ? C4 C3 H3 118.8 ? C2 C3 H3 118.8 ? C5 C4 C3 117.5(3) ? C5 C4 C7 121.4(3) ? C3 C4 C7 121.2(3) ? C4 C5 C6 122.0(3) ? C4 C5 H5 119.0 ? C6 C5 H5 119.0 ? C1 C6 C5 119.4(3) ? C1 C6 H6 120.3 ? C5 C6 H6 120.3 ? C4 C7 H7A 109.5 ? C4 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? C4 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? C8 N1 H1A 111.0(16) ? C8 N1 H1B 110.5(16) ? H1A N1 H1B 108(2) ? C8 N1 H1C 108.9(17) ? H1A N1 H1C 112(2) ? H1B N1 H1C 105(2) ? C10 C8 C9 110.3(2) y C10 C8 N1 111.1(2) y C9 C8 N1 109.7(2) y C10 C8 H8 109.8(14) ? C9 C8 H8 108.7(15) ? N1 C8 H8 107.1(14) ? N2 C9 C8 177.8(3) ? N3 C10 C8 179.5(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 1.449(3) ? S1 O2 1.453(3) ? S1 O1 1.457(2) ? S1 C1 1.752(4) ? C1 C6 1.370(4) ? C1 C2 1.372(4) ? C2 C3 1.380(5) ? C2 H2 .9300 ? C3 C4 1.369(5) ? C3 H3 .9300 ? C4 C5 1.362(5) ? C4 C7 1.515(5) ? C5 C6 1.376(5) ? C5 H5 .9300 ? C6 H6 .9300 ? C7 H7A .9600 ? C7 H7B .9600 ? C7 H7C .9600 ? N1 C8 1.473(4) y N1 H1A .91(3) ? N1 H1B .93(3) ? N1 H1C .92(3) ? N2 C9 1.127(4) y N3 C10 1.120(4) y C8 C10 1.469(4) y C8 C9 1.473(4) y C8 H8 .95(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 N1 H1A O2 1_556 .91(3) 1.84(3) 2.741(4) 175(2) N1 H1B O3 4_566 .93(3) 1.78(3) 2.701(4) 168(2) N1 H1C O1 4_666 .92(3) 1.87(3) 2.778(5) 167(3) C8 H8 O1 . .95(3) 2.35(2) 3.075(5) 132.3(19) C8 H8 O2 4_666 .95(3) 2.73(2) 3.373(5) 125.8(17) C8 H8 N2 1_655 .95(3) 2.78(3) 3.409(6) 124.2(17) 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 O3 S1 C1 C6 48.8(2) O2 S1 C1 C6 169.4(2) O1 S1 C1 C6 -71.1(2) O3 S1 C1 C2 -133.3(2) O2 S1 C1 C2 -12.7(2) O1 S1 C1 C2 106.8(2) C6 C1 C2 C3 -.2(4) S1 C1 C2 C3 -178.2(2) C1 C2 C3 C4 .3(5) C2 C3 C4 C5 .1(5) C2 C3 C4 C7 179.5(3) C3 C4 C5 C6 -.5(5) C7 C4 C5 C6 -179.9(3) C2 C1 C6 C5 -.2(4) S1 C1 C6 C5 177.8(2) C4 C5 C6 C1 .5(5) C10 C8 C9 N2 -172(8) N1 C8 C9 N2 66(8) C9 C8 C10 N3 7E1(4) N1 C8 C10 N3 -17E1(10)