#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2205121.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_2205121 loop_ _publ_author_name 'Coe, Benjamin J.' 'Hall, Jonathan J.' 'Harris, James A.' 'Brunschwig, B. S.' 'Coles, Simon J.' 'Hursthouse, Michael B.' _publ_section_title ; trans-4-[(4-Dimethylaminophenyl)ethenyl]-N-methylquinolinium p-toluenesulfonate monohydrate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o464 _journal_page_last o467 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C20 H21 N2 + , C7 H7 O3 S - , H2 O' _chemical_formula_sum 'C27 H30 N2 O4 S' _chemical_formula_weight 478.59 _chemical_name_systematic ; trans-4-[(4-Dimethylaminophenyl)ethenyl]-N-methylquinolinium p-toluenesulfonate monohydrate ; _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 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 97.75(7) _cell_angle_beta 97.87(4) _cell_angle_gamma 103.97(5) _cell_formula_units_Z 2 _cell_length_a 8.033(4) _cell_length_b 10.550(7) _cell_length_c 14.662(9) _cell_measurement_reflns_used 4905 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 1176.2(12) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'Please provide missing details' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 22326 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.19 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_T_max 0.9759 _exptl_absorpt_correction_T_min 0.9022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour 'dark green' _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 508 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.282 _refine_diff_density_min -0.528 _refine_ls_extinction_coef 0.016(4) _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 1.02 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 320 _refine_ls_number_reflns 5337 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.02 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.045 _refine_ls_shift/su_max 0.047 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.4268P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1126 _refine_ls_wR_factor_ref 0.1258 _reflns_number_gt 4160 _reflns_number_total 5337 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh6354.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 0.1870(2) 0.49093(15) 0.22545(11) 0.0239(3) Uani d . 1 C C2 0.0344(2) 0.50065(17) 0.25634(12) 0.0289(4) Uani d . 1 C H2 0.0382 0.538 0.3195 0.035 Uiso calc R 1 H C3 -0.1235(2) 0.45625(18) 0.19555(13) 0.0323(4) Uani d . 1 C H3 -0.2272 0.4648 0.2171 0.039 Uiso calc R 1 H C4 -0.1321(2) 0.39965(18) 0.10393(13) 0.0345(4) Uani d . 1 C C5 0.0215(3) 0.3901(2) 0.07428(13) 0.0433(5) Uani d . 1 C H5 0.0175 0.3516 0.0113 0.052 Uiso calc R 1 H C6 0.1807(2) 0.4353(2) 0.13394(12) 0.0363(4) Uani d . 1 C H6 0.2846 0.4281 0.1121 0.044 Uiso calc R 1 H C7 -0.3049(3) 0.3485(2) 0.03880(16) 0.0515(6) Uani d . 1 C H7A -0.383 0.2823 0.0653 0.077 Uiso calc R 1 H H7B -0.2874 0.3076 -0.022 0.077 Uiso calc R 1 H H7C -0.3567 0.4222 0.0307 0.077 Uiso calc R 1 H C8 -0.2581(3) 1.0018(3) 0.06957(14) 0.0482(5) Uani d . 1 C H8A -0.2393 1.083 0.1152 0.072 Uiso calc R 1 H H8B -0.3833 0.9591 0.0516 0.072 Uiso calc R 1 H H8C -0.2099 1.0239 0.0141 0.072 Uiso calc R 1 H C9 -0.2729(2) 0.7774(2) 0.10750(15) 0.0456(5) Uani d . 1 C H9A -0.2615 0.721 0.0511 0.068 Uiso calc R 1 H H9B -0.3956 0.7759 0.1061 0.068 Uiso calc R 1 H H9C -0.2302 0.7441 0.163 0.068 Uiso calc R 1 H C10 0.0046(2) 0.94966(19) 0.14200(11) 0.0309(4) Uani d . 1 C C11 0.0997(2) 1.08193(19) 0.15017(12) 0.0325(4) Uani d . 1 C H11 0.0428 1.1451 0.1301 0.039 Uiso calc R 1 H C12 0.2753(2) 1.12140(18) 0.18701(12) 0.0297(4) Uani d . 1 C H12 0.3365 1.212 0.1925 0.036 Uiso calc R 1 H C13 0.3662(2) 1.03238(16) 0.21654(11) 0.0259(3) Uani d . 1 C C14 0.2719(2) 0.89901(17) 0.20550(11) 0.0269(4) Uani d . 1 C H14 0.3301 0.8355 0.2235 0.032 Uiso calc R 1 H C15 0.0966(2) 0.85853(18) 0.16909(11) 0.0293(4) Uani d . 1 C H15 0.0364 0.7675 0.162 0.035 Uiso calc R 1 H C16 0.5484(2) 1.08135(16) 0.25871(11) 0.0252(3) Uani d . 1 C H16 0.6008 1.1726 0.2599 0.03 Uiso calc R 1 H C17 0.6520(2) 1.01168(16) 0.29644(11) 0.0245(3) Uani d . 1 C H17 0.6014 0.9209 0.2978 0.029 Uiso calc R 1 H C18 0.83523(19) 1.06637(15) 0.33494(11) 0.0226(3) Uani d . 1 C C19 0.9158(2) 1.20092(16) 0.34417(12) 0.0267(3) Uani d . 1 C H19 0.8495 1.259 0.3249 0.032 Uiso calc R 1 H C20 1.0898(2) 1.25077(15) 0.38084(11) 0.0260(3) Uani d . 1 C H20 1.1401 1.3434 0.3872 0.031 Uiso calc R 1 H C21 1.3748(2) 1.23849(17) 0.44935(12) 0.0298(4) Uani d . 1 C H21A 1.3997 1.3342 0.4498 0.045 Uiso calc R 1 H H21B 1.4499 1.2011 0.4123 0.045 Uiso calc R 1 H H21C 1.3973 1.2223 0.5136 0.045 Uiso calc R 1 H C22 0.94211(19) 0.98455(15) 0.36645(10) 0.0216(3) Uani d . 1 C C23 1.1223(2) 1.04052(15) 0.40176(10) 0.0219(3) Uani d . 1 C C24 1.2294(2) 0.96115(16) 0.43134(11) 0.0264(3) Uani d . 1 C H24 1.3508 0.9991 0.4523 0.032 Uiso calc R 1 H C25 1.1585(2) 0.82932(17) 0.42985(12) 0.0290(4) Uani d . 1 C H25 1.2308 0.7756 0.4499 0.035 Uiso calc R 1 H C26 0.9798(2) 0.77316(16) 0.39892(12) 0.0280(4) Uani d . 1 C H26 0.9308 0.6823 0.4006 0.034 Uiso calc R 1 H C27 0.8751(2) 0.84764(15) 0.36628(11) 0.0243(3) Uani d . 1 C H27 0.7551 0.8067 0.343 0.029 Uiso calc R 1 H N1 -0.17163(19) 0.91167(18) 0.11094(11) 0.0405(4) Uani d . 1 N N2 1.19082(16) 1.17505(13) 0.40782(9) 0.0235(3) Uani d . 1 N O1 0.34481(16) 0.55102(12) 0.39676(8) 0.0347(3) Uani d . 1 O O2 0.48631(16) 0.45316(13) 0.28231(9) 0.0391(3) Uani d . 1 O O3 0.46894(16) 0.67913(13) 0.28613(11) 0.0452(4) Uani d . 1 O S1 0.38860(5) 0.54905(4) 0.30368(3) 0.02578(14) Uani d . 1 S O4 0.76791(17) 0.45303(13) 0.42219(11) 0.0367(3) Uani d . 1 O H10 0.673(3) 0.457(2) 0.3841(18) 0.058(7) Uiso d . 1 H H2O 0.740(3) 0.450(2) 0.4763(17) 0.043(6) 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 C1 0.0200(7) 0.0216(7) 0.0291(8) 0.0037(6) 0.0026(6) 0.0065(6) C2 0.0259(8) 0.0303(9) 0.0300(9) 0.0077(6) 0.0049(7) 0.0026(7) C3 0.0210(8) 0.0374(9) 0.0403(10) 0.0086(7) 0.0064(7) 0.0111(8) C4 0.0263(9) 0.0379(10) 0.0363(10) 0.0064(7) -0.0029(7) 0.0085(8) C5 0.0372(10) 0.0642(13) 0.0260(9) 0.0189(9) -0.0026(8) -0.0026(9) C6 0.0268(9) 0.0564(12) 0.0287(9) 0.0164(8) 0.0062(7) 0.0061(8) C7 0.0310(10) 0.0609(14) 0.0530(13) 0.0075(9) -0.0131(9) 0.0063(10) C8 0.0304(10) 0.0841(16) 0.0351(10) 0.0246(10) 0.0014(8) 0.0144(10) C9 0.0243(9) 0.0614(13) 0.0407(11) 0.0043(8) 0.0002(8) -0.0086(9) C10 0.0230(8) 0.0478(11) 0.0214(8) 0.0107(7) 0.0038(6) 0.0016(7) C11 0.0295(9) 0.0433(10) 0.0291(9) 0.0176(8) 0.0046(7) 0.0073(7) C12 0.0283(9) 0.0329(9) 0.0288(9) 0.0098(7) 0.0061(7) 0.0044(7) C13 0.0215(8) 0.0324(9) 0.0236(8) 0.0074(6) 0.0051(6) 0.0029(7) C14 0.0232(8) 0.0324(9) 0.0246(8) 0.0085(6) 0.0032(6) 0.0019(7) C15 0.0233(8) 0.0369(9) 0.0246(8) 0.0051(7) 0.0036(6) 0.0003(7) C16 0.0230(8) 0.0263(8) 0.0250(8) 0.0049(6) 0.0056(6) 0.0022(6) C17 0.0208(8) 0.0247(8) 0.0259(8) 0.0037(6) 0.0040(6) 0.0018(6) C18 0.0206(7) 0.0238(8) 0.0218(7) 0.0038(6) 0.0050(6) 0.0017(6) C19 0.0256(8) 0.0235(8) 0.0305(9) 0.0062(6) 0.0033(7) 0.0054(7) C20 0.0271(8) 0.0204(8) 0.0289(8) 0.0029(6) 0.0056(6) 0.0047(6) C21 0.0194(8) 0.0303(9) 0.0335(9) -0.0007(6) -0.0001(7) 0.0018(7) C22 0.0221(7) 0.0211(7) 0.0202(7) 0.0035(6) 0.0056(6) 0.0008(6) C23 0.0218(7) 0.0225(8) 0.0201(7) 0.0037(6) 0.0051(6) 0.0015(6) C24 0.0229(8) 0.0291(8) 0.0266(8) 0.0076(6) 0.0033(6) 0.0027(6) C25 0.0312(9) 0.0287(8) 0.0303(9) 0.0134(7) 0.0061(7) 0.0050(7) C26 0.0315(9) 0.0226(8) 0.0307(9) 0.0072(6) 0.0103(7) 0.0024(7) C27 0.0237(8) 0.0221(8) 0.0249(8) 0.0030(6) 0.0066(6) 0.0005(6) N1 0.0213(7) 0.0603(11) 0.0371(9) 0.0114(7) -0.0014(6) 0.0044(8) N2 0.0196(6) 0.0229(7) 0.0240(7) 0.0006(5) 0.0022(5) 0.0012(5) O1 0.0312(7) 0.0368(7) 0.0277(6) 0.0002(5) -0.0011(5) -0.0009(5) O2 0.0274(6) 0.0419(7) 0.0451(8) 0.0168(5) -0.0062(5) -0.0039(6) O3 0.0298(7) 0.0310(7) 0.0664(9) -0.0075(5) -0.0052(6) 0.0215(6) S1 0.0194(2) 0.0226(2) 0.0321(2) 0.00188(14) -0.00032(15) 0.00509(16) O4 0.0290(7) 0.0443(8) 0.0389(8) 0.0131(6) 0.0054(6) 0.0084(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 1.379(3) ? C1 C2 1.385(2) ? C1 S1 1.771(2) ? C2 C3 1.384(3) ? C2 H2 0.95 ? C3 C4 1.380(3) ? C3 H3 0.95 ? C4 C5 1.384(3) ? C4 C7 1.506(3) ? C5 C6 1.384(3) ? C5 H5 0.95 ? C6 H6 0.95 ? C7 H7A 0.98 ? C7 H7B 0.98 ? C7 H7C 0.98 ? C8 N1 1.453(3) yes C8 H8A 0.98 ? C8 H8B 0.98 ? C8 H8C 0.98 ? C9 N1 1.444(3) yes C9 H9A 0.98 ? C9 H9B 0.98 ? C9 H9C 0.98 ? C10 N1 1.368(2) yes C10 C11 1.400(3) yes C10 C15 1.413(3) yes C11 C12 1.379(3) yes C11 H11 0.95 ? C12 C13 1.399(2) yes C12 H12 0.95 ? C13 C14 1.404(3) yes C13 C16 1.447(2) yes C14 C15 1.375(2) yes C14 H14 0.95 ? C15 H15 0.95 ? C16 C17 1.348(2) yes C16 H16 0.95 ? C17 C18 1.447(2) yes C17 H17 0.95 ? C18 C19 1.390(2) yes C18 C22 1.433(2) yes C19 C20 1.372(2) yes C19 H19 0.95 ? C20 N2 1.328(2) yes C20 H20 0.95 ? C21 N2 1.473(2) yes C21 H21A 0.98 ? C21 H21B 0.98 ? C21 H21C 0.98 ? C22 C27 1.414(2) yes C22 C23 1.418(2) yes C23 N2 1.379(2) yes C23 C24 1.405(2) yes C24 C25 1.366(2) yes C24 H24 0.95 ? C25 C26 1.398(3) yes C25 H25 0.95 ? C26 C27 1.365(2) yes C26 H26 0.95 ? C27 H27 0.95 ? O1 S1 1.4540(15) ? O2 S1 1.4502(15) ? O3 S1 1.4419(16) ? O4 H10 0.90(3) ? O4 H2O 0.86(2) ? 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 C6 C1 C2 119.68(16) ? C6 C1 S1 120.42(13) ? C2 C1 S1 119.90(13) ? C3 C2 C1 120.28(17) ? C3 C2 H2 119.9 ? C1 C2 H2 119.9 ? C4 C3 C2 120.72(17) ? C4 C3 H3 119.6 ? C2 C3 H3 119.6 ? C3 C4 C5 118.28(16) ? C3 C4 C7 120.44(18) ? C5 C4 C7 121.28(19) ? C4 C5 C6 121.72(18) ? C4 C5 H5 119.1 ? C6 C5 H5 119.1 ? C1 C6 C5 119.32(17) ? 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 ? N1 C8 H8A 109.5 ? N1 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? N1 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? N1 C9 H9A 109.5 ? N1 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? N1 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? N1 C10 C11 120.83(17) yes N1 C10 C15 121.65(17) yes C11 C10 C15 117.51(16) yes C12 C11 C10 120.62(17) yes C12 C11 H11 119.7 ? C10 C11 H11 119.7 ? C11 C12 C13 122.12(17) yes C11 C12 H12 118.9 ? C13 C12 H12 118.9 ? C12 C13 C14 117.18(15) yes C12 C13 C16 119.35(16) yes C14 C13 C16 123.45(16) yes C15 C14 C13 121.21(16) yes C15 C14 H14 119.4 ? C13 C14 H14 119.4 ? C14 C15 C10 121.29(17) yes C14 C15 H15 119.4 ? C10 C15 H15 119.4 ? C17 C16 C13 127.15(15) yes C17 C16 H16 116.4 ? C13 C16 H16 116.4 ? C16 C17 C18 124.17(15) yes C16 C17 H17 117.9 ? C18 C17 H17 117.9 ? C19 C18 C22 116.75(15) yes C19 C18 C17 121.72(15) yes C22 C18 C17 121.53(14) yes C20 C19 C18 120.79(16) yes C20 C19 H19 119.6 ? C18 C19 H19 119.6 ? N2 C20 C19 122.84(15) yes N2 C20 H20 118.6 ? C19 C20 H20 118.6 ? N2 C21 H21A 109.5 ? N2 C21 H21B 109.5 ? H21A C21 H21B 109.5 ? N2 C21 H21C 109.5 ? H21A C21 H21C 109.5 ? H21B C21 H21C 109.5 ? C27 C22 C23 117.05(15) yes C27 C22 C18 122.72(14) yes C23 C22 C18 120.21(14) yes N2 C23 C24 120.25(14) yes N2 C23 C22 118.87(15) yes C24 C23 C22 120.87(15) yes C25 C24 C23 119.84(15) yes C25 C24 H24 120.1 ? C23 C24 H24 120.1 ? C24 C25 C26 120.22(16) yes C24 C25 H25 119.9 ? C26 C25 H25 119.9 ? C27 C26 C25 120.68(15) yes C27 C26 H26 119.7 ? C25 C26 H26 119.7 ? C26 C27 C22 121.24(15) yes C26 C27 H27 119.4 ? C22 C27 H27 119.4 ? C10 N1 C9 121.38(17) yes C10 N1 C8 120.21(18) yes C9 N1 C8 117.97(17) yes C20 N2 C23 120.50(14) yes C20 N2 C21 118.80(14) yes C23 N2 C21 120.61(14) yes O3 S1 O2 113.25(10) ? O3 S1 O1 113.06(10) ? O2 S1 O1 111.98(9) ? O3 S1 C1 106.47(9) ? O2 S1 C1 105.80(9) ? O1 S1 C1 105.52(9) ? H10 O4 H2O 107(2) ? 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 O4 H2O O1 2_666 0.86(2) 2.07(2) 2.922(3) 175(2) yes O4 H10 O2 . 0.89(2) 1.95(3) 2.838(3) 169(2) yes C14 H14 O3 . 0.95 2.41 3.359(3) 174 yes C17 H17 O3 . 0.95 2.49 3.435(3) 175 yes C27 H27 O3 . 0.95 2.34 3.282(3) 172 yes C3 H3 O2 1_455 0.95 2.59 3.535(3) 171 yes C20 H20 O1 1_665 0.95 2.37 3.290(3) 162 yes _cod_database_code 2205121