Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _audit_update_record ; 2007-01-11 # Formatted by publCIF ; _publ_contact_author_name 'Xuan-Ming Duan' _publ_contact_author_address ; Technical Institute of Physics and Chemistry Chinese Academy of Sciences No. 2 Zhongguancunbeiyitiao, Haidian Beijing 100180 P. R. China ; _publ_contact_author_email xmduan@mail.ipc.ac.cn _publ_contact_author_Fax 0086-10-8254-3597 _publ_contact_author_Phone 0086-10-8254-3596 _publ_section_title ; From supermolecular sheet to helix via breaking molecular symmetry: a case of 4-[2-(carbazol-3-yl)vinyl]pyridium tosylate ; loop_ _publ_author_name 'Xuan-Ming Duan.' 'Wei-Qiang Chen.' 'Jie Gu.' 'Daisuke Hashizume' 'Tatsuo Wada' data_compound_tosylate _database_code_depnum_ccdc_archive 'CCDC 287149' _chemical_name_systematic ; 1-methyl-4-[2-(9-ethyl carbazol-3-yl)vinyl]pyridinium tosylate ; _audit_creation_method SHELXL-97 _chemical_name_common '1-methyl-4-(2-(9-ethyl carbazol-3-yl)vinyl)pyridinium tosylate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H28 N2 O3 S' _chemical_formula_weight 484.59 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.7781(9) _cell_length_b 13.5566(18) _cell_length_c 26.631(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2447.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1982 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 19.66 _exptl_crystal_description PRISM _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.743664 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13385 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4301 _reflns_number_gt 3093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.22(9) _refine_ls_number_reflns 4301 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.03832(11) 0.23854(5) 0.16446(3) 0.0480(2) Uani 1 1 d . . . O1 O -0.0361(3) 0.13391(13) 0.15780(9) 0.0672(6) Uani 1 1 d . . . O2 O 0.0701(4) 0.26620(17) 0.20935(8) 0.0792(7) Uani 1 1 d . . . O3 O -0.2284(3) 0.28235(18) 0.16188(11) 0.0939(9) Uani 1 1 d . . . N1 N 1.6647(3) 0.47279(16) 0.26666(9) 0.0419(6) Uani 1 1 d . . . N2 N 0.3455(3) 0.72606(17) 0.09044(9) 0.0487(6) Uani 1 1 d . . . C1 C 1.4576(5) 0.6088(2) 0.25427(12) 0.0524(8) Uani 1 1 d . . . H1 H 1.4339 0.6757 0.2593 0.063 Uiso 1 1 calc R . . C2 C 1.6285(4) 0.5683(2) 0.27206(12) 0.0482(8) Uani 1 1 d . . . H2 H 1.7205 0.6082 0.2881 0.058 Uiso 1 1 calc R . . C3 C 1.8475(5) 0.4297(2) 0.28757(13) 0.0590(9) Uani 1 1 d . . . H3A H 1.9364 0.4817 0.2969 0.088 Uiso 1 1 calc R . . H3B H 1.9088 0.3885 0.2627 0.088 Uiso 1 1 calc R . . H3C H 1.8159 0.3909 0.3166 0.088 Uiso 1 1 calc R . . C4 C 1.5314(5) 0.4152(2) 0.24334(12) 0.0556(9) Uani 1 1 d . . . H4 H 1.5564 0.3481 0.2398 0.067 Uiso 1 1 calc R . . C5 C 1.3609(5) 0.4535(2) 0.22484(13) 0.0536(8) Uani 1 1 d . . . H5 H 1.2708 0.4119 0.2092 0.064 Uiso 1 1 calc R . . C6 C 1.3189(4) 0.5529(2) 0.22888(11) 0.0456(7) Uani 1 1 d . . . C7 C 1.1436(5) 0.5999(2) 0.20797(12) 0.0526(8) Uani 1 1 d . . . H7 H 1.1249 0.6665 0.2151 0.063 Uiso 1 1 calc R . . C8 C 1.0099(4) 0.5564(2) 0.18001(12) 0.0517(8) Uani 1 1 d . . . H8 H 1.0284 0.4893 0.1743 0.062 Uiso 1 1 calc R . . C9 C 0.8358(4) 0.6003(2) 0.15674(11) 0.0468(7) Uani 1 1 d . . . C10 C 0.6957(4) 0.5376(2) 0.13521(12) 0.0514(8) Uani 1 1 d . . . H10 H 0.7171 0.4699 0.1365 0.062 Uiso 1 1 calc R . . C11 C 0.5282(5) 0.5718(2) 0.11228(12) 0.0527(8) Uani 1 1 d . . . H11 H 0.4369 0.5287 0.0982 0.063 Uiso 1 1 calc R . . C12 C 0.5002(4) 0.6729(2) 0.11097(11) 0.0439(7) Uani 1 1 d . . . C13 C 0.1834(4) 0.6835(2) 0.06161(12) 0.0570(8) Uani 1 1 d . . . H13A H 0.0670 0.7244 0.0657 0.068 Uiso 1 1 calc R . . H13B H 0.1531 0.6185 0.0748 0.068 Uiso 1 1 calc R . . C14 C 0.2307(5) 0.6748(3) 0.00661(13) 0.0784(11) Uani 1 1 d . . . H14A H 0.2486 0.7394 -0.0074 0.118 Uiso 1 1 calc R . . H14B H 0.1240 0.6421 -0.0103 0.118 Uiso 1 1 calc R . . H14C H 0.3496 0.6372 0.0024 0.118 Uiso 1 1 calc R . . C15 C 0.3850(4) 0.8258(2) 0.09569(11) 0.0435(7) Uani 1 1 d . . . C16 C 0.2785(5) 0.9072(2) 0.07946(12) 0.0575(9) Uani 1 1 d . . . H16 H 0.1589 0.8995 0.0628 0.069 Uiso 1 1 calc R . . C17 C 0.3542(6) 0.9995(2) 0.08870(14) 0.0680(10) Uani 1 1 d . . . H17 H 0.2830 1.0548 0.0787 0.082 Uiso 1 1 calc R . . C18 C 0.5332(5) 1.0120(2) 0.11243(13) 0.0618(9) Uani 1 1 d . . . H18 H 0.5831 1.0753 0.1170 0.074 Uiso 1 1 calc R . . C19 C 0.6391(5) 0.9318(2) 0.12941(11) 0.0504(8) Uani 1 1 d . . . H19 H 0.7580 0.9407 0.1462 0.060 Uiso 1 1 calc R . . C20 C 0.5659(4) 0.8378(2) 0.12105(10) 0.0429(7) Uani 1 1 d . . . C21 C 0.6382(4) 0.7393(2) 0.13121(10) 0.0412(6) Uani 1 1 d . . . C22 C 0.8055(4) 0.7027(2) 0.15510(11) 0.0471(7) Uani 1 1 d . . . H22 H 0.8960 0.7454 0.1698 0.057 Uiso 1 1 calc R . . C23 C 0.4454(7) 0.3953(3) -0.01042(16) 0.0942(13) Uani 1 1 d . . . H23A H 0.5533 0.4341 0.0020 0.141 Uiso 1 1 d R . . H23B H 0.3637 0.4352 -0.0317 0.141 Uiso 1 1 d R . . H23C H 0.4958 0.3404 -0.0292 0.141 Uiso 1 1 d R . . C24 C 0.3254(6) 0.3579(2) 0.03299(14) 0.0608(9) Uani 1 1 d . . . C25 C 0.4085(5) 0.3050(2) 0.07112(14) 0.0654(10) Uani 1 1 d . . . H25 H 0.5429 0.2914 0.0698 0.079 Uiso 1 1 calc R . . C26 C 0.3011(4) 0.2711(2) 0.11137(12) 0.0534(8) Uani 1 1 d . . . H26 H 0.3637 0.2366 0.1370 0.064 Uiso 1 1 calc R . . C27 C 0.1003(4) 0.28807(18) 0.11384(11) 0.0412(7) Uani 1 1 d . . . C28 C 0.0123(5) 0.3411(2) 0.07610(12) 0.0564(9) Uani 1 1 d . . . H28 H -0.1225 0.3536 0.0773 0.068 Uiso 1 1 calc R . . C29 C 0.1240(6) 0.3763(2) 0.03577(13) 0.0661(10) Uani 1 1 d . . . H29 H 0.0628 0.4125 0.0105 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0474(4) 0.0409(4) 0.0557(5) 0.0027(4) 0.0078(4) 0.0017(3) O1 0.0819(15) 0.0403(11) 0.0795(17) -0.0011(11) 0.0162(15) -0.0120(11) O2 0.1095(18) 0.0811(15) 0.0469(13) -0.0072(13) 0.0045(14) -0.0358(15) O3 0.0586(13) 0.1042(19) 0.119(2) 0.0495(18) 0.0365(16) 0.0357(13) N1 0.0424(14) 0.0399(14) 0.0435(16) 0.0005(11) 0.0015(13) 0.0007(11) N2 0.0443(13) 0.0605(16) 0.0415(15) -0.0021(13) -0.0086(12) 0.0026(12) C1 0.0615(19) 0.0382(16) 0.058(2) -0.0071(15) -0.0072(19) 0.0054(15) C2 0.0491(18) 0.0396(17) 0.056(2) -0.0041(14) -0.0085(17) 0.0002(14) C3 0.0500(18) 0.063(2) 0.064(2) 0.0082(17) 0.0016(18) 0.0146(16) C4 0.064(2) 0.0358(15) 0.067(2) -0.0056(15) 0.001(2) 0.0038(16) C5 0.0494(17) 0.0492(19) 0.062(2) -0.0075(16) -0.0103(18) -0.0080(15) C6 0.0459(17) 0.0468(18) 0.0440(19) 0.0027(14) 0.0052(16) 0.0051(14) C7 0.0576(18) 0.0443(17) 0.056(2) -0.0036(16) 0.0012(18) 0.0038(15) C8 0.0548(19) 0.0503(18) 0.050(2) 0.0020(15) 0.0091(17) 0.0064(15) C9 0.0487(17) 0.0507(17) 0.0409(18) 0.0069(15) 0.0059(16) 0.0143(14) C10 0.057(2) 0.0442(17) 0.053(2) 0.0020(15) 0.0060(18) 0.0019(15) C11 0.0550(19) 0.0511(18) 0.052(2) -0.0010(15) -0.0054(18) -0.0027(16) C12 0.0428(17) 0.0520(17) 0.0370(17) 0.0001(13) 0.0000(15) 0.0063(13) C13 0.0452(17) 0.072(2) 0.054(2) 0.0023(17) -0.0073(17) -0.0055(16) C14 0.075(2) 0.109(3) 0.051(2) -0.012(2) -0.009(2) -0.005(2) C15 0.0435(16) 0.0534(18) 0.0336(18) -0.0032(15) 0.0014(15) 0.0070(14) C16 0.0568(19) 0.070(2) 0.046(2) 0.0006(17) -0.0080(17) 0.0187(18) C17 0.082(2) 0.057(2) 0.064(2) 0.0018(19) -0.008(2) 0.0211(19) C18 0.076(2) 0.0523(19) 0.057(2) -0.0020(16) -0.006(2) 0.0116(18) C19 0.0541(18) 0.0541(19) 0.043(2) -0.0060(15) -0.0062(17) 0.0049(15) C20 0.0451(17) 0.0512(17) 0.0322(17) -0.0061(13) -0.0044(15) 0.0080(14) C21 0.0407(14) 0.0495(16) 0.0333(15) 0.0000(14) 0.0020(13) 0.0068(14) C22 0.0410(16) 0.0580(19) 0.0423(19) 0.0015(15) -0.0002(15) 0.0009(13) C23 0.122(3) 0.074(2) 0.086(3) 0.005(2) 0.045(3) -0.015(3) C24 0.075(2) 0.0471(18) 0.061(2) -0.0061(17) 0.019(2) -0.0084(17) C25 0.0482(19) 0.068(2) 0.080(3) 0.000(2) 0.016(2) -0.0010(16) C26 0.0464(17) 0.0538(18) 0.060(2) 0.0086(17) 0.0021(17) 0.0011(14) C27 0.0455(17) 0.0345(15) 0.0437(18) -0.0040(13) 0.0017(14) 0.0010(11) C28 0.0516(18) 0.0570(18) 0.061(2) 0.0054(16) 0.0067(18) 0.0035(15) C29 0.088(3) 0.062(2) 0.049(2) 0.0093(17) -0.002(2) 0.0055(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.420(2) . ? S1 O1 1.4296(19) . ? S1 O2 1.452(2) . ? S1 C27 1.775(3) . ? N1 C2 1.326(3) . ? N1 C4 1.346(4) . ? N1 C3 1.479(4) . ? N2 C12 1.385(3) . ? N2 C15 1.386(3) . ? N2 C13 1.460(4) . ? C1 C2 1.367(4) . ? C1 C6 1.385(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.359(4) . ? C4 H4 0.9300 . ? C5 C6 1.382(4) . ? C5 H5 0.9300 . ? C6 C7 1.459(4) . ? C7 C8 1.313(4) . ? C7 H7 0.9300 . ? C8 C9 1.460(4) . ? C8 H8 0.9300 . ? C9 C10 1.397(4) . ? C9 C22 1.404(4) . ? C10 C11 1.370(4) . ? C10 H10 0.9300 . ? C11 C12 1.385(4) . ? C11 H11 0.9300 . ? C12 C21 1.405(4) . ? C13 C14 1.504(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.388(4) . ? C15 C20 1.409(4) . ? C16 C17 1.374(4) . ? C16 H16 0.9300 . ? C17 C18 1.379(5) . ? C17 H17 0.9300 . ? C18 C19 1.379(4) . ? C18 H18 0.9300 . ? C19 C20 1.386(4) . ? C19 H19 0.9300 . ? C20 C21 1.448(4) . ? C21 C22 1.392(4) . ? C22 H22 0.9300 . ? C23 C24 1.502(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.365(4) . ? C24 C29 1.390(5) . ? C25 C26 1.375(4) . ? C25 H25 0.9300 . ? C26 C27 1.382(4) . ? C26 H26 0.9300 . ? C27 C28 1.372(4) . ? C28 C29 1.398(4) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O1 114.73(16) . . ? O3 S1 O2 113.01(18) . . ? O1 S1 O2 110.67(15) . . ? O3 S1 C27 106.56(14) . . ? O1 S1 C27 105.99(13) . . ? O2 S1 C27 105.05(13) . . ? C2 N1 C4 119.5(2) . . ? C2 N1 C3 120.0(2) . . ? C4 N1 C3 120.5(2) . . ? C12 N2 C15 108.8(2) . . ? C12 N2 C13 124.9(2) . . ? C15 N2 C13 125.8(2) . . ? C2 C1 C6 121.6(3) . . ? C2 C1 H1 119.2 . . ? C6 C1 H1 119.2 . . ? N1 C2 C1 120.8(3) . . ? N1 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C5 121.1(3) . . ? N1 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 115.6(3) . . ? C5 C6 C7 124.4(3) . . ? C1 C6 C7 120.0(3) . . ? C8 C7 C6 125.6(3) . . ? C8 C7 H7 117.2 . . ? C6 C7 H7 117.2 . . ? C7 C8 C9 128.0(3) . . ? C7 C8 H8 116.0 . . ? C9 C8 H8 116.0 . . ? C10 C9 C22 119.3(3) . . ? C10 C9 C8 118.4(3) . . ? C22 C9 C8 122.3(3) . . ? C11 C10 C9 122.7(3) . . ? C11 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C10 C11 C12 117.3(3) . . ? C10 C11 H11 121.3 . . ? C12 C11 H11 121.3 . . ? C11 C12 N2 129.0(3) . . ? C11 C12 C21 122.2(3) . . ? N2 C12 C21 108.8(2) . . ? N2 C13 C14 112.5(3) . . ? N2 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N2 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 130.1(3) . . ? N2 C15 C20 109.2(2) . . ? C16 C15 C20 120.7(3) . . ? C17 C16 C15 118.3(3) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C18 121.5(3) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C19 120.7(3) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C20 119.1(3) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C19 C20 C15 119.6(3) . . ? C19 C20 C21 134.2(3) . . ? C15 C20 C21 106.1(2) . . ? C22 C21 C12 119.3(3) . . ? C22 C21 C20 133.6(3) . . ? C12 C21 C20 107.1(2) . . ? C21 C22 C9 119.0(3) . . ? C21 C22 H22 120.5 . . ? C9 C22 H22 120.5 . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C24 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 117.4(3) . . ? C25 C24 C23 121.8(3) . . ? C29 C24 C23 120.8(4) . . ? C24 C25 C26 122.5(3) . . ? C24 C25 H25 118.8 . . ? C26 C25 H25 118.8 . . ? C25 C26 C27 120.2(3) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 118.7(3) . . ? C28 C27 S1 121.6(2) . . ? C26 C27 S1 119.6(2) . . ? C27 C28 C29 120.4(3) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C24 C29 C28 120.7(3) . . ? C24 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C2 C1 0.1(4) . . . . ? C3 N1 C2 C1 -178.1(3) . . . . ? C6 C1 C2 N1 -1.8(5) . . . . ? C2 N1 C4 C5 0.5(5) . . . . ? C3 N1 C4 C5 178.7(3) . . . . ? N1 C4 C5 C6 0.6(5) . . . . ? C4 C5 C6 C1 -2.2(5) . . . . ? C4 C5 C6 C7 177.1(3) . . . . ? C2 C1 C6 C5 2.8(5) . . . . ? C2 C1 C6 C7 -176.5(3) . . . . ? C5 C6 C7 C8 -4.7(5) . . . . ? C1 C6 C7 C8 174.5(3) . . . . ? C6 C7 C8 C9 -177.7(3) . . . . ? C7 C8 C9 C10 -169.8(3) . . . . ? C7 C8 C9 C22 10.6(5) . . . . ? C22 C9 C10 C11 0.0(5) . . . . ? C8 C9 C10 C11 -179.7(3) . . . . ? C9 C10 C11 C12 0.0(5) . . . . ? C10 C11 C12 N2 -179.9(3) . . . . ? C10 C11 C12 C21 1.3(4) . . . . ? C15 N2 C12 C11 -177.0(3) . . . . ? C13 N2 C12 C11 -5.3(5) . . . . ? C15 N2 C12 C21 2.0(3) . . . . ? C13 N2 C12 C21 173.7(2) . . . . ? C12 N2 C13 C14 -87.2(4) . . . . ? C15 N2 C13 C14 83.1(4) . . . . ? C12 N2 C15 C16 177.3(3) . . . . ? C13 N2 C15 C16 5.7(5) . . . . ? C12 N2 C15 C20 -1.4(3) . . . . ? C13 N2 C15 C20 -173.0(3) . . . . ? N2 C15 C16 C17 -178.5(3) . . . . ? C20 C15 C16 C17 0.1(4) . . . . ? C15 C16 C17 C18 1.4(5) . . . . ? C16 C17 C18 C19 -2.4(5) . . . . ? C17 C18 C19 C20 1.8(5) . . . . ? C18 C19 C20 C15 -0.3(4) . . . . ? C18 C19 C20 C21 176.9(3) . . . . ? N2 C15 C20 C19 178.2(3) . . . . ? C16 C15 C20 C19 -0.7(4) . . . . ? N2 C15 C20 C21 0.3(3) . . . . ? C16 C15 C20 C21 -178.6(3) . . . . ? C11 C12 C21 C22 -2.4(4) . . . . ? N2 C12 C21 C22 178.5(2) . . . . ? C11 C12 C21 C20 177.3(3) . . . . ? N2 C12 C21 C20 -1.7(3) . . . . ? C19 C20 C21 C22 3.1(5) . . . . ? C15 C20 C21 C22 -179.4(3) . . . . ? C19 C20 C21 C12 -176.6(3) . . . . ? C15 C20 C21 C12 0.9(3) . . . . ? C12 C21 C22 C9 2.3(4) . . . . ? C20 C21 C22 C9 -177.3(3) . . . . ? C10 C9 C22 C21 -1.2(4) . . . . ? C8 C9 C22 C21 178.5(3) . . . . ? C29 C24 C25 C26 -0.5(5) . . . . ? C23 C24 C25 C26 179.3(3) . . . . ? C24 C25 C26 C27 1.5(5) . . . . ? C25 C26 C27 C28 -1.5(5) . . . . ? C25 C26 C27 S1 176.9(2) . . . . ? O3 S1 C27 C28 -12.0(3) . . . . ? O1 S1 C27 C28 110.7(2) . . . . ? O2 S1 C27 C28 -132.1(3) . . . . ? O3 S1 C27 C26 169.7(3) . . . . ? O1 S1 C27 C26 -67.7(3) . . . . ? O2 S1 C27 C26 49.6(3) . . . . ? C26 C27 C28 C29 0.5(4) . . . . ? S1 C27 C28 C29 -177.8(2) . . . . ? C25 C24 C29 C28 -0.4(5) . . . . ? C23 C24 C29 C28 179.7(3) . . . . ? C27 C28 C29 C24 0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.182 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.034 data_1 _database_code_depnum_ccdc_archive 'CCDC 633346' _chemical_name_systematic ; N-methyl-4-[2-(9-methyl carbazol-3-yl)vinyl]pyridinium 2-methyl-5-nitro benzenesulfonate ; _audit_creation_method SHELXL-97 _chemical_name_common ; N-methyl-4-(2-(9-methyl carbazol-3-yl)vinyl)pyridinium 2- methyl-5-nitro benzenesulfonate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H25 N3 O5 S' _chemical_formula_weight 515.57 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 14.569(4) _cell_length_b 25.121(7) _cell_length_c 6.7399(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.743(5) _cell_angle_gamma 90.00 _cell_volume 2449.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1183 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 19.83 _exptl_crystal_description LABLLER _exptl_crystal_colour RED _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.349866 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13220 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0858 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4297 _reflns_number_gt 2490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0318P)^2^+1.1114P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4297 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1072 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.11748(5) 0.62611(3) 0.26274(14) 0.0494(3) Uani 1 1 d . . . O1 O 0.14114(15) 0.60184(9) 0.0799(3) 0.0650(7) Uani 1 1 d . . . O2 O 0.09490(15) 0.58682(9) 0.4076(4) 0.0657(7) Uani 1 1 d . . . O3 O 0.05185(14) 0.66883(9) 0.2306(4) 0.0727(8) Uani 1 1 d . . . O4 O 0.4607(2) 0.63821(16) 0.1156(7) 0.1317(15) Uani 1 1 d . . . O5 O 0.53232(19) 0.69339(13) 0.3204(6) 0.1237(13) Uani 1 1 d . . . N1 N 0.25570(18) 0.00176(9) 0.2510(4) 0.0437(6) Uani 1 1 d . . . N2 N 0.15898(16) 0.42361(9) 0.2170(4) 0.0398(6) Uani 1 1 d . . . N3 N 0.4637(2) 0.66749(15) 0.2591(7) 0.0858(12) Uani 1 1 d . . . C1 C 0.2970(2) 0.09247(12) 0.2709(4) 0.0422(8) Uani 1 1 d . . . H1 H 0.3432 0.1181 0.2906 0.051 Uiso 1 1 calc R . . C2 C 0.3202(2) 0.04007(12) 0.2798(5) 0.0450(8) Uani 1 1 d . . . H2 H 0.3821 0.0305 0.3063 0.054 Uiso 1 1 calc R . . C3 C 0.2825(2) -0.05503(11) 0.2607(5) 0.0583(10) Uani 1 1 d . . . H3A H 0.2883 -0.0678 0.1285 0.088 Uiso 1 1 calc R . . H3B H 0.2361 -0.0753 0.3173 0.088 Uiso 1 1 calc R . . H3C H 0.3406 -0.0589 0.3427 0.088 Uiso 1 1 calc R . . C4 C 0.1665(2) 0.01532(13) 0.2127(5) 0.0504(9) Uani 1 1 d . . . H4 H 0.1220 -0.0113 0.1921 0.060 Uiso 1 1 calc R . . C5 C 0.1397(2) 0.06710(12) 0.2033(5) 0.0478(8) Uani 1 1 d . . . H5 H 0.0772 0.0753 0.1770 0.057 Uiso 1 1 calc R . . C6 C 0.20450(19) 0.10834(11) 0.2325(4) 0.0377(7) Uani 1 1 d . . . C7 C 0.1746(2) 0.16297(11) 0.2233(4) 0.0404(7) Uani 1 1 d . . . H7 H 0.1114 0.1695 0.2044 0.049 Uiso 1 1 calc R . . C8 C 0.2312(2) 0.20492(11) 0.2400(4) 0.0397(7) Uani 1 1 d . . . H8 H 0.2941 0.1973 0.2591 0.048 Uiso 1 1 calc R . . C9 C 0.20666(19) 0.26110(11) 0.2320(4) 0.0375(7) Uani 1 1 d . . . C10 C 0.27702(19) 0.29863(11) 0.2537(4) 0.0381(7) Uani 1 1 d . . . H10 H 0.3383 0.2876 0.2727 0.046 Uiso 1 1 calc R . . C11 C 0.25625(19) 0.35266(11) 0.2471(4) 0.0353(7) Uani 1 1 d . . . C12 C 0.31124(19) 0.40042(11) 0.2652(4) 0.0357(7) Uani 1 1 d . . . C13 C 0.4051(2) 0.41076(12) 0.2906(5) 0.0476(8) Uani 1 1 d . . . H13 H 0.4476 0.3830 0.3007 0.057 Uiso 1 1 calc R . . C14 C 0.4348(2) 0.46289(13) 0.3007(5) 0.0556(9) Uani 1 1 d . . . H14 H 0.4977 0.4702 0.3193 0.067 Uiso 1 1 calc R . . C15 C 0.3718(2) 0.50474(13) 0.2835(5) 0.0554(9) Uani 1 1 d . . . H15 H 0.3936 0.5395 0.2914 0.066 Uiso 1 1 calc R . . C16 C 0.2782(2) 0.49601(12) 0.2551(4) 0.0474(8) Uani 1 1 d . . . H16 H 0.2366 0.5242 0.2428 0.057 Uiso 1 1 calc R . . C17 C 0.24810(19) 0.44360(11) 0.2453(4) 0.0381(7) Uani 1 1 d . . . C18 C 0.0742(2) 0.45482(13) 0.1907(5) 0.0562(9) Uani 1 1 d . . . H18A H 0.0403 0.4466 0.0635 0.084 Uiso 1 1 calc R . . H18B H 0.0892 0.4920 0.1961 0.084 Uiso 1 1 calc R . . H18C H 0.0371 0.4464 0.2952 0.084 Uiso 1 1 calc R . . C19 C 0.16321(18) 0.36870(11) 0.2187(4) 0.0363(7) Uani 1 1 d . . . C20 C 0.0913(2) 0.33175(12) 0.1941(4) 0.0434(8) Uani 1 1 d . . . H20 H 0.0300 0.3427 0.1730 0.052 Uiso 1 1 calc R . . C21 C 0.11403(19) 0.27897(12) 0.2022(4) 0.0425(8) Uani 1 1 d . . . H21 H 0.0668 0.2539 0.1875 0.051 Uiso 1 1 calc R . . C22 C 0.1428(3) 0.69254(15) 0.6684(6) 0.0716(11) Uani 1 1 d . . . H22A H 0.1005 0.7162 0.5927 0.107 Uiso 1 1 calc R . . H22B H 0.1624 0.7080 0.7968 0.107 Uiso 1 1 calc R . . H22C H 0.1128 0.6591 0.6859 0.107 Uiso 1 1 calc R . . C23 C 0.2257(2) 0.68362(11) 0.5584(5) 0.0480(8) Uani 1 1 d . . . C24 C 0.22209(19) 0.65645(11) 0.3754(5) 0.0397(8) Uani 1 1 d . . . C25 C 0.3002(2) 0.65080(11) 0.2807(5) 0.0461(8) Uani 1 1 d . . . H25 H 0.2973 0.6327 0.1596 0.055 Uiso 1 1 calc R . . C26 C 0.3826(2) 0.67203(13) 0.3661(6) 0.0549(10) Uani 1 1 d . . . C27 C 0.3888(3) 0.69788(13) 0.5472(7) 0.0671(11) Uani 1 1 d . . . H27 H 0.4449 0.7116 0.6052 0.081 Uiso 1 1 calc R . . C28 C 0.3110(3) 0.70289(13) 0.6396(6) 0.0630(10) Uani 1 1 d . . . H28 H 0.3154 0.7200 0.7627 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0337(4) 0.0480(5) 0.0649(6) 0.0009(5) -0.0010(4) -0.0013(4) O1 0.0626(15) 0.0737(16) 0.0570(16) -0.0206(13) 0.0001(12) -0.0048(12) O2 0.0583(15) 0.0592(14) 0.0803(19) 0.0151(13) 0.0108(13) -0.0182(12) O3 0.0404(13) 0.0702(16) 0.104(2) 0.0071(15) -0.0068(13) 0.0147(12) O4 0.080(2) 0.152(3) 0.178(4) -0.047(3) 0.075(2) -0.014(2) O5 0.0442(17) 0.118(2) 0.211(4) 0.005(2) 0.026(2) -0.0235(17) N1 0.0512(17) 0.0377(14) 0.0436(17) -0.0043(12) 0.0108(13) -0.0030(13) N2 0.0366(14) 0.0418(15) 0.0407(16) -0.0001(12) 0.0026(11) 0.0073(12) N3 0.041(2) 0.071(2) 0.149(4) 0.009(2) 0.023(2) 0.0013(18) C1 0.0426(19) 0.0393(18) 0.045(2) -0.0007(15) 0.0062(15) -0.0065(14) C2 0.0404(18) 0.046(2) 0.049(2) 0.0006(15) 0.0057(15) -0.0011(16) C3 0.078(2) 0.0372(19) 0.060(3) -0.0010(17) 0.0120(19) 0.0003(17) C4 0.047(2) 0.048(2) 0.057(2) -0.0073(17) 0.0094(17) -0.0130(16) C5 0.0387(18) 0.049(2) 0.056(2) -0.0041(16) 0.0060(15) -0.0057(16) C6 0.0394(17) 0.0445(18) 0.0294(18) -0.0018(14) 0.0054(13) -0.0014(14) C7 0.0371(17) 0.0456(18) 0.039(2) -0.0009(15) 0.0071(14) 0.0011(15) C8 0.0380(17) 0.0455(18) 0.036(2) 0.0023(14) 0.0060(14) -0.0014(15) C9 0.0379(17) 0.0410(17) 0.0334(18) -0.0003(14) 0.0038(13) 0.0001(14) C10 0.0324(16) 0.0462(19) 0.0356(19) 0.0026(14) 0.0044(13) 0.0067(14) C11 0.0351(16) 0.0418(17) 0.0291(18) 0.0019(13) 0.0046(13) 0.0026(13) C12 0.0340(16) 0.0412(17) 0.0316(18) -0.0002(14) 0.0030(13) 0.0014(14) C13 0.0424(19) 0.0482(19) 0.053(2) 0.0023(16) 0.0072(15) 0.0023(15) C14 0.0419(19) 0.060(2) 0.066(3) -0.0004(19) 0.0090(17) -0.0083(17) C15 0.062(2) 0.045(2) 0.059(2) -0.0029(17) 0.0064(19) -0.0108(17) C16 0.060(2) 0.0380(18) 0.045(2) -0.0013(15) 0.0052(16) 0.0045(16) C17 0.0384(17) 0.0435(18) 0.0323(19) 0.0003(14) 0.0040(13) 0.0009(14) C18 0.045(2) 0.060(2) 0.062(3) -0.0017(18) 0.0011(17) 0.0163(17) C19 0.0348(17) 0.0442(18) 0.0297(18) 0.0013(14) 0.0036(13) 0.0031(14) C20 0.0305(16) 0.052(2) 0.047(2) -0.0020(16) 0.0027(14) 0.0026(15) C21 0.0380(17) 0.0479(19) 0.041(2) -0.0009(15) 0.0024(14) -0.0059(14) C22 0.082(3) 0.067(2) 0.070(3) -0.011(2) 0.029(2) 0.004(2) C23 0.054(2) 0.0359(17) 0.055(2) 0.0012(16) 0.0067(17) 0.0025(15) C24 0.0341(17) 0.0329(16) 0.051(2) 0.0037(15) 0.0013(15) 0.0022(13) C25 0.0383(19) 0.0385(18) 0.061(2) 0.0029(16) 0.0053(17) 0.0036(14) C26 0.0317(18) 0.0429(19) 0.091(3) 0.013(2) 0.0084(18) 0.0046(15) C27 0.053(2) 0.048(2) 0.094(3) 0.001(2) -0.019(2) -0.0068(18) C28 0.069(3) 0.050(2) 0.067(3) -0.0107(18) -0.005(2) -0.0058(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.437(2) . ? S1 O1 1.452(2) . ? S1 O2 1.453(2) . ? S1 C24 1.791(3) . ? O4 N3 1.212(4) . ? O5 N3 1.224(4) . ? N1 C4 1.339(4) . ? N1 C2 1.343(4) . ? N1 C3 1.479(4) . ? N2 C19 1.381(3) . ? N2 C17 1.384(3) . ? N2 C18 1.456(3) . ? N3 C26 1.458(5) . ? C1 C2 1.359(4) . ? C1 C6 1.400(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.358(4) . ? C4 H4 0.9300 . ? C5 C6 1.400(4) . ? C5 H5 0.9300 . ? C6 C7 1.439(4) . ? C7 C8 1.334(4) . ? C7 H7 0.9300 . ? C8 C9 1.455(4) . ? C8 H8 0.9300 . ? C9 C10 1.388(4) . ? C9 C21 1.414(4) . ? C10 C11 1.390(4) . ? C10 H10 0.9300 . ? C11 C19 1.406(4) . ? C11 C12 1.440(4) . ? C12 C13 1.383(4) . ? C12 C17 1.418(4) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.391(4) . ? C14 H14 0.9300 . ? C15 C16 1.371(4) . ? C15 H15 0.9300 . ? C16 C17 1.387(4) . ? C16 H16 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.394(4) . ? C20 C21 1.366(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.506(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C28 1.386(4) . ? C23 C24 1.405(4) . ? C24 C25 1.376(4) . ? C25 C26 1.377(4) . ? C25 H25 0.9300 . ? C26 C27 1.376(5) . ? C27 C28 1.361(5) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O1 113.93(16) . . ? O3 S1 O2 114.19(15) . . ? O1 S1 O2 112.34(15) . . ? O3 S1 C24 105.32(14) . . ? O1 S1 C24 105.27(14) . . ? O2 S1 C24 104.63(14) . . ? C4 N1 C2 119.5(3) . . ? C4 N1 C3 120.0(3) . . ? C2 N1 C3 120.5(3) . . ? C19 N2 C17 108.7(2) . . ? C19 N2 C18 125.1(2) . . ? C17 N2 C18 126.2(2) . . ? O4 N3 O5 122.9(4) . . ? O4 N3 C26 119.1(4) . . ? O5 N3 C26 117.9(4) . . ? C2 C1 C6 120.8(3) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? N1 C2 C1 121.5(3) . . ? N1 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C5 121.4(3) . . ? N1 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 115.7(3) . . ? C5 C6 C7 120.3(3) . . ? C1 C6 C7 124.0(3) . . ? C8 C7 C6 124.7(3) . . ? C8 C7 H7 117.7 . . ? C6 C7 H7 117.7 . . ? C7 C8 C9 128.1(3) . . ? C7 C8 H8 116.0 . . ? C9 C8 H8 116.0 . . ? C10 C9 C21 118.7(3) . . ? C10 C9 C8 118.7(2) . . ? C21 C9 C8 122.6(3) . . ? C9 C10 C11 120.3(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C19 119.1(3) . . ? C10 C11 C12 134.0(3) . . ? C19 C11 C12 106.9(2) . . ? C13 C12 C17 119.3(3) . . ? C13 C12 C11 134.4(3) . . ? C17 C12 C11 106.3(2) . . ? C14 C13 C12 118.9(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 120.9(3) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C16 C15 C14 121.7(3) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C17 117.5(3) . . ? C15 C16 H16 121.2 . . ? C17 C16 H16 121.2 . . ? N2 C17 C16 129.6(3) . . ? N2 C17 C12 108.8(2) . . ? C16 C17 C12 121.5(3) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C20 129.2(3) . . ? N2 C19 C11 109.2(2) . . ? C20 C19 C11 121.6(3) . . ? C21 C20 C19 117.8(3) . . ? C21 C20 H20 121.1 . . ? C19 C20 H20 121.1 . . ? C20 C21 C9 122.4(3) . . ? C20 C21 H21 118.8 . . ? C9 C21 H21 118.8 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 117.1(3) . . ? C28 C23 C22 119.2(3) . . ? C24 C23 C22 123.7(3) . . ? C25 C24 C23 120.7(3) . . ? C25 C24 S1 117.9(2) . . ? C23 C24 S1 121.4(2) . . ? C24 C25 C26 119.6(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 121.1(3) . . ? C27 C26 N3 120.2(4) . . ? C25 C26 N3 118.7(4) . . ? C28 C27 C26 118.6(3) . . ? C28 C27 H27 120.7 . . ? C26 C27 H27 120.7 . . ? C27 C28 C23 122.9(4) . . ? C27 C28 H28 118.5 . . ? C23 C28 H28 118.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C2 C1 0.0(5) . . . . ? C3 N1 C2 C1 179.8(3) . . . . ? C6 C1 C2 N1 0.4(5) . . . . ? C2 N1 C4 C5 -0.3(5) . . . . ? C3 N1 C4 C5 179.8(3) . . . . ? N1 C4 C5 C6 0.3(5) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C4 C5 C6 C7 -179.5(3) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? C2 C1 C6 C7 179.2(3) . . . . ? C5 C6 C7 C8 -176.8(3) . . . . ? C1 C6 C7 C8 3.6(5) . . . . ? C6 C7 C8 C9 179.8(3) . . . . ? C7 C8 C9 C10 179.8(3) . . . . ? C7 C8 C9 C21 -0.5(5) . . . . ? C21 C9 C10 C11 0.4(4) . . . . ? C8 C9 C10 C11 -179.9(3) . . . . ? C9 C10 C11 C19 0.1(4) . . . . ? C9 C10 C11 C12 179.6(3) . . . . ? C10 C11 C12 C13 2.0(6) . . . . ? C19 C11 C12 C13 -178.5(3) . . . . ? C10 C11 C12 C17 -179.9(3) . . . . ? C19 C11 C12 C17 -0.4(3) . . . . ? C17 C12 C13 C14 1.5(5) . . . . ? C11 C12 C13 C14 179.5(3) . . . . ? C12 C13 C14 C15 -0.7(5) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? C14 C15 C16 C17 0.4(5) . . . . ? C19 N2 C17 C16 -179.8(3) . . . . ? C18 N2 C17 C16 -0.1(5) . . . . ? C19 N2 C17 C12 0.2(3) . . . . ? C18 N2 C17 C12 179.8(3) . . . . ? C15 C16 C17 N2 -179.6(3) . . . . ? C15 C16 C17 C12 0.4(5) . . . . ? C13 C12 C17 N2 178.6(3) . . . . ? C11 C12 C17 N2 0.1(3) . . . . ? C13 C12 C17 C16 -1.4(4) . . . . ? C11 C12 C17 C16 -179.9(3) . . . . ? C17 N2 C19 C20 -179.3(3) . . . . ? C18 N2 C19 C20 1.0(5) . . . . ? C17 N2 C19 C11 -0.4(3) . . . . ? C18 N2 C19 C11 179.9(3) . . . . ? C10 C11 C19 N2 -179.9(3) . . . . ? C12 C11 C19 N2 0.5(3) . . . . ? C10 C11 C19 C20 -0.9(4) . . . . ? C12 C11 C19 C20 179.5(3) . . . . ? N2 C19 C20 C21 180.0(3) . . . . ? C11 C19 C20 C21 1.2(4) . . . . ? C19 C20 C21 C9 -0.7(5) . . . . ? C10 C9 C21 C20 -0.1(4) . . . . ? C8 C9 C21 C20 -179.8(3) . . . . ? C28 C23 C24 C25 -1.6(4) . . . . ? C22 C23 C24 C25 178.5(3) . . . . ? C28 C23 C24 S1 176.1(2) . . . . ? C22 C23 C24 S1 -3.8(4) . . . . ? O3 S1 C24 C25 -122.3(2) . . . . ? O1 S1 C24 C25 -1.6(3) . . . . ? O2 S1 C24 C25 117.0(2) . . . . ? O3 S1 C24 C23 59.9(3) . . . . ? O1 S1 C24 C23 -179.3(2) . . . . ? O2 S1 C24 C23 -60.8(3) . . . . ? C23 C24 C25 C26 -0.1(4) . . . . ? S1 C24 C25 C26 -177.8(2) . . . . ? C24 C25 C26 C27 1.4(5) . . . . ? C24 C25 C26 N3 -177.5(3) . . . . ? O4 N3 C26 C27 169.3(4) . . . . ? O5 N3 C26 C27 -10.1(5) . . . . ? O4 N3 C26 C25 -11.7(6) . . . . ? O5 N3 C26 C25 168.9(3) . . . . ? C25 C26 C27 C28 -1.1(5) . . . . ? N3 C26 C27 C28 177.9(3) . . . . ? C26 C27 C28 C23 -0.7(5) . . . . ? C24 C23 C28 C27 2.0(5) . . . . ? C22 C23 C28 C27 -178.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.239 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.049 # Attachment 'MeCMP-TsO.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 633347' _audit_creation_method SHELXL-97 _chemical_name_systematic '1-methyl-4-[2-(9-methyl carbazol-3-yl)vinyl]pyridinium tosylate' _chemical_name_common ;1-methyl-4-(2-(9-methyl carbazol-3-yl)vinyl)pyridinium tosylate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H19 N2, C7 H7 O3 S' _chemical_formula_sum 'C28 H26 N2 O3 S' _chemical_formula_weight 470.57 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.6773(6) _cell_length_b 14.0015(15) _cell_length_c 24.593(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2299.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110 _cell_measurement_reflns_used 11918 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.597 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16089 _diffrn_reflns_av_R_equivalents 0.1448 _diffrn_reflns_av_sigmaI/netI 0.1214 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 24.40 _reflns_number_total 3726 _reflns_number_gt 2373 _reflns_threshold_expression I>2\s(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+0.5641P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(14) _refine_ls_number_reflns 3726 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.02727(19) 0.77637(10) 0.67213(5) 0.0295(3) Uani 1 1 d . . . O1 O 0.0401(5) 0.8785(2) 0.66128(12) 0.0367(9) Uani 1 1 d . . . O2 O 0.2178(4) 0.7271(3) 0.67149(13) 0.0436(10) Uani 1 1 d . . . O3 O -0.0918(5) 0.7553(2) 0.72088(11) 0.0312(9) Uani 1 1 d . . . N1 N 0.6565(6) 0.2734(3) 0.57123(15) 0.0316(11) Uani 1 1 d . . . N2 N -0.6564(6) 0.5411(3) 0.76523(15) 0.0285(11) Uani 1 1 d . . . C1 C 0.2015(7) 0.3115(4) 0.64515(17) 0.0284(13) Uani 1 1 d . . . H1 H 0.1053 0.2721 0.6627 0.034 Uiso 1 1 calc R . . C2 C 0.1817(7) 0.4105(4) 0.64511(18) 0.0279(13) Uani 1 1 d . . . C3 C 0.3284(7) 0.4676(4) 0.62040(19) 0.0311(13) Uani 1 1 d . . . H3 H 0.3141 0.5350 0.6213 0.037 Uiso 1 1 calc R . . C4 C 0.4924(8) 0.4286(4) 0.5948(2) 0.0346(13) Uani 1 1 d . . . H4 H 0.5909 0.4682 0.5785 0.041 Uiso 1 1 calc R . . C5 C 0.5099(7) 0.3310(4) 0.59364(18) 0.0276(12) Uani 1 1 d . . . C6 C 0.6083(7) 0.1779(4) 0.57961(18) 0.0293(13) Uani 1 1 d . . . C7 C 0.7086(8) 0.0964(4) 0.5643(2) 0.0409(15) Uani 1 1 d . . . H7 H 0.8296 0.0997 0.5441 0.049 Uiso 1 1 calc R . . C8 C 0.6281(8) 0.0103(4) 0.5792(2) 0.0412(15) Uani 1 1 d . . . H8 H 0.6974 -0.0466 0.5699 0.049 Uiso 1 1 calc R . . C9 C 0.4473(8) 0.0034(4) 0.6078(2) 0.0384(14) Uani 1 1 d . . . H9 H 0.3944 -0.0576 0.6166 0.046 Uiso 1 1 calc R . . C10 C 0.3454(8) 0.0850(4) 0.6231(2) 0.0376(14) Uani 1 1 d . . . H10 H 0.2223 0.0807 0.6424 0.045 Uiso 1 1 calc R . . C11 C 0.4268(7) 0.1739(4) 0.60991(18) 0.0284(13) Uani 1 1 d . . . C12 C 0.3677(7) 0.2715(4) 0.61850(17) 0.0276(12) Uani 1 1 d . . . C13 C 0.8235(7) 0.3075(4) 0.5377(2) 0.0423(16) Uani 1 1 d . . . H13A H 0.8527 0.3742 0.5469 0.063 Uiso 1 1 calc R . . H13B H 0.7871 0.3030 0.4992 0.063 Uiso 1 1 calc R . . H13C H 0.9421 0.2682 0.5447 0.063 Uiso 1 1 calc R . . C14 C 0.0080(7) 0.4574(4) 0.6709(2) 0.0336(13) Uani 1 1 d . . . H14 H -0.0033 0.5247 0.6670 0.040 Uiso 1 1 calc R . . C15 C -0.1347(8) 0.4129(4) 0.69947(18) 0.0299(13) Uani 1 1 d . . . H15 H -0.1219 0.3460 0.7050 0.036 Uiso 1 1 calc R . . C16 C -0.3107(7) 0.4614(4) 0.72289(19) 0.0265(12) Uani 1 1 d . . . C17 C -0.3442(8) 0.5590(4) 0.7217(2) 0.0328(13) Uani 1 1 d . . . H17 H -0.2462 0.5999 0.7061 0.039 Uiso 1 1 calc R . . C18 C -0.5141(8) 0.5970(4) 0.74243(19) 0.0320(13) Uani 1 1 d . . . H18 H -0.5338 0.6642 0.7410 0.038 Uiso 1 1 calc R . . C19 C -0.6283(7) 0.4464(4) 0.76814(19) 0.0263(13) Uani 1 1 d . . . H19 H -0.7274 0.4074 0.7848 0.032 Uiso 1 1 calc R . . C20 C -0.4600(8) 0.4055(4) 0.74761(19) 0.0291(12) Uani 1 1 d . . . H20 H -0.4429 0.3383 0.7500 0.035 Uiso 1 1 calc R . . C21 C -0.8370(8) 0.5855(4) 0.7891(2) 0.0351(14) Uani 1 1 d . . . H21A H -0.8917 0.6326 0.7637 0.053 Uiso 1 1 calc R . . H21B H -0.8013 0.6172 0.8233 0.053 Uiso 1 1 calc R . . H21C H -0.9376 0.5361 0.7962 0.053 Uiso 1 1 calc R . . C22 C -0.1158(7) 0.7272(4) 0.61824(16) 0.0254(12) Uani 1 1 d . . . C23 C -0.0297(8) 0.6684(3) 0.57910(18) 0.0296(12) Uani 1 1 d . . . H23 H 0.1090 0.6536 0.5811 0.036 Uiso 1 1 calc R . . C24 C -0.1450(9) 0.6309(4) 0.53696(19) 0.0351(14) Uani 1 1 d . . . H24 H -0.0849 0.5898 0.5109 0.042 Uiso 1 1 calc R . . C25 C -0.3476(8) 0.6532(4) 0.53277(19) 0.0334(14) Uani 1 1 d . . . C26 C -0.4304(7) 0.7118(4) 0.57209(19) 0.0347(13) Uani 1 1 d . . . H26 H -0.5686 0.7274 0.5700 0.042 Uiso 1 1 calc R . . C27 C -0.3174(7) 0.7482(3) 0.61422(19) 0.0285(13) Uani 1 1 d . . . H27 H -0.3786 0.7881 0.6407 0.034 Uiso 1 1 calc R . . C28 C -0.4742(10) 0.6116(4) 0.4880(2) 0.0529(17) Uani 1 1 d . . . H28A H -0.3946 0.6071 0.4546 0.079 Uiso 1 1 calc R . . H28B H -0.5903 0.6529 0.4816 0.079 Uiso 1 1 calc R . . H28C H -0.5202 0.5478 0.4986 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0275(7) 0.0275(8) 0.0336(6) -0.0012(7) -0.0045(7) -0.0025(7) O1 0.043(2) 0.026(2) 0.0406(19) 0.0008(17) -0.0043(18) -0.0089(19) O2 0.0240(18) 0.062(3) 0.044(2) -0.006(2) -0.0045(18) 0.0098(19) O3 0.041(2) 0.031(2) 0.0213(15) 0.0026(16) -0.0003(16) -0.0092(16) N1 0.025(2) 0.036(3) 0.033(2) 0.005(2) 0.006(2) -0.001(2) N2 0.026(2) 0.027(3) 0.032(2) -0.003(2) 0.001(2) 0.006(2) C1 0.024(3) 0.036(4) 0.025(3) 0.005(2) -0.003(2) 0.004(3) C2 0.024(3) 0.031(4) 0.029(3) 0.002(2) -0.005(2) 0.002(3) C3 0.029(3) 0.027(4) 0.037(3) 0.010(3) 0.000(3) -0.004(3) C4 0.034(3) 0.029(4) 0.041(3) 0.010(3) 0.003(3) -0.005(3) C5 0.017(3) 0.037(3) 0.028(3) 0.005(2) 0.001(2) 0.005(3) C6 0.026(3) 0.038(4) 0.024(3) 0.003(3) -0.003(3) 0.003(3) C7 0.035(3) 0.051(5) 0.037(3) -0.004(3) 0.007(3) 0.005(3) C8 0.039(4) 0.038(4) 0.046(3) -0.006(3) 0.010(3) 0.009(3) C9 0.042(4) 0.036(4) 0.038(3) 0.001(3) 0.004(3) 0.000(3) C10 0.032(3) 0.042(4) 0.039(3) 0.000(3) -0.005(3) 0.003(3) C11 0.027(3) 0.036(4) 0.022(2) 0.006(3) -0.002(3) 0.000(3) C12 0.027(3) 0.028(4) 0.028(3) 0.001(3) -0.005(2) 0.000(3) C13 0.024(3) 0.056(5) 0.047(3) 0.006(3) 0.007(3) -0.004(3) C14 0.031(3) 0.032(3) 0.038(3) 0.005(3) -0.008(3) 0.002(3) C15 0.028(3) 0.028(4) 0.035(3) 0.003(2) -0.003(3) 0.004(3) C16 0.028(3) 0.024(3) 0.027(3) 0.001(2) -0.004(3) 0.003(3) C17 0.031(3) 0.028(4) 0.040(3) 0.005(3) -0.008(3) 0.001(3) C18 0.033(3) 0.020(3) 0.043(3) 0.003(3) -0.001(3) -0.001(3) C19 0.026(3) 0.023(4) 0.030(3) 0.006(2) -0.003(3) 0.000(2) C20 0.033(3) 0.018(3) 0.037(3) 0.006(2) 0.000(3) -0.001(3) C21 0.027(3) 0.041(4) 0.037(3) -0.002(3) 0.004(3) 0.008(3) C22 0.031(3) 0.025(3) 0.021(2) 0.000(2) -0.003(2) -0.008(2) C23 0.028(3) 0.024(3) 0.036(3) -0.001(3) 0.000(3) -0.001(3) C24 0.055(4) 0.022(3) 0.029(3) 0.000(2) 0.002(3) -0.005(3) C25 0.045(4) 0.026(4) 0.030(3) 0.003(3) -0.004(3) -0.009(3) C26 0.030(3) 0.030(3) 0.044(3) 0.006(3) -0.004(3) -0.005(3) C27 0.023(3) 0.022(3) 0.040(3) 0.002(2) -0.001(3) -0.007(2) C28 0.076(5) 0.039(4) 0.044(3) 0.000(3) -0.028(3) -0.025(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.447(3) . ? S1 O1 1.457(3) . ? S1 O3 1.469(3) . ? S1 C22 1.773(4) . ? N1 C5 1.383(6) . ? N1 C6 1.390(6) . ? N1 C13 1.466(6) . ? N2 C19 1.341(6) . ? N2 C18 1.354(6) . ? N2 C21 1.478(6) . ? C1 C2 1.393(7) . ? C1 C12 1.406(6) . ? C1 H1 0.9500 . ? C2 C3 1.402(7) . ? C2 C14 1.477(7) . ? C3 C4 1.375(7) . ? C3 H3 0.9500 . ? C4 C5 1.372(7) . ? C4 H4 0.9500 . ? C5 C12 1.404(7) . ? C6 C7 1.375(7) . ? C6 C11 1.424(6) . ? C7 C8 1.370(7) . ? C7 H7 0.9500 . ? C8 C9 1.400(7) . ? C8 H8 0.9500 . ? C9 C10 1.382(7) . ? C9 H9 0.9500 . ? C10 C11 1.396(7) . ? C10 H10 0.9500 . ? C11 C12 1.438(7) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.337(6) . ? C14 H14 0.9500 . ? C15 C16 1.474(7) . ? C15 H15 0.9500 . ? C16 C17 1.385(7) . ? C16 C20 1.405(7) . ? C17 C18 1.353(7) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.359(7) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C27 1.381(6) . ? C22 C23 1.391(6) . ? C23 C24 1.394(6) . ? C23 H23 0.9500 . ? C24 C25 1.392(7) . ? C24 H24 0.9500 . ? C25 C26 1.384(7) . ? C25 C28 1.506(7) . ? C26 C27 1.379(6) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 114.5(2) . . ? O2 S1 O3 112.9(2) . . ? O1 S1 O3 112.3(2) . . ? O2 S1 C22 106.3(2) . . ? O1 S1 C22 106.0(2) . . ? O3 S1 C22 103.92(19) . . ? C5 N1 C6 109.8(4) . . ? C5 N1 C13 124.9(5) . . ? C6 N1 C13 124.9(4) . . ? C19 N2 C18 119.8(4) . . ? C19 N2 C21 120.6(4) . . ? C18 N2 C21 119.6(5) . . ? C2 C1 C12 118.1(5) . . ? C2 C1 H1 121.0 . . ? C12 C1 H1 121.0 . . ? C1 C2 C3 120.1(5) . . ? C1 C2 C14 121.1(5) . . ? C3 C2 C14 118.8(5) . . ? C4 C3 C2 121.9(5) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C5 C4 C3 118.2(5) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 N1 130.5(5) . . ? C4 C5 C12 121.6(5) . . ? N1 C5 C12 107.8(5) . . ? C7 C6 N1 130.1(5) . . ? C7 C6 C11 121.6(6) . . ? N1 C6 C11 108.2(5) . . ? C8 C7 C6 117.8(5) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 121.1 . . ? C7 C8 C9 122.3(6) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C10 C9 C8 120.3(6) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 118.7(5) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C6 119.3(5) . . ? C10 C11 C12 134.9(5) . . ? C6 C11 C12 105.8(5) . . ? C5 C12 C1 120.0(5) . . ? C5 C12 C11 108.4(4) . . ? C1 C12 C11 131.6(5) . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C2 125.3(5) . . ? C15 C14 H14 117.3 . . ? C2 C14 H14 117.3 . . ? C14 C15 C16 123.9(5) . . ? C14 C15 H15 118.0 . . ? C16 C15 H15 118.0 . . ? C17 C16 C20 116.3(5) . . ? C17 C16 C15 125.1(5) . . ? C20 C16 C15 118.6(5) . . ? C18 C17 C16 121.1(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 N2 121.1(5) . . ? C17 C18 H18 119.4 . . ? N2 C18 H18 119.4 . . ? N2 C19 C20 120.8(5) . . ? N2 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C19 C20 C16 120.9(5) . . ? C19 C20 H20 119.6 . . ? C16 C20 H20 119.6 . . ? 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 118.7(4) . . ? C27 C22 S1 119.7(4) . . ? C23 C22 S1 121.6(4) . . ? C22 C23 C24 120.6(5) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 120.5(5) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 118.0(5) . . ? C26 C25 C28 121.1(5) . . ? C24 C25 C28 120.8(5) . . ? C27 C26 C25 121.7(5) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C26 C27 C22 120.5(5) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 C1 C2 C3 -1.9(7) . . . . ? C12 C1 C2 C14 178.3(4) . . . . ? C1 C2 C3 C4 1.2(7) . . . . ? C14 C2 C3 C4 -179.0(5) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C3 C4 C5 N1 -179.9(4) . . . . ? C3 C4 C5 C12 -1.2(7) . . . . ? C6 N1 C5 C4 -179.2(5) . . . . ? C13 N1 C5 C4 -6.4(8) . . . . ? C6 N1 C5 C12 1.9(5) . . . . ? C13 N1 C5 C12 174.7(4) . . . . ? C5 N1 C6 C7 179.6(5) . . . . ? C13 N1 C6 C7 6.8(8) . . . . ? C5 N1 C6 C11 -1.7(5) . . . . ? C13 N1 C6 C11 -174.5(4) . . . . ? N1 C6 C7 C8 178.5(5) . . . . ? C11 C6 C7 C8 0.0(7) . . . . ? C6 C7 C8 C9 1.8(8) . . . . ? C7 C8 C9 C10 -1.6(8) . . . . ? C8 C9 C10 C11 -0.3(7) . . . . ? C9 C10 C11 C6 1.9(7) . . . . ? C9 C10 C11 C12 180.0(5) . . . . ? C7 C6 C11 C10 -1.8(6) . . . . ? N1 C6 C11 C10 179.3(5) . . . . ? C7 C6 C11 C12 179.6(5) . . . . ? N1 C6 C11 C12 0.8(5) . . . . ? C4 C5 C12 C1 0.5(7) . . . . ? N1 C5 C12 C1 179.5(4) . . . . ? C4 C5 C12 C11 179.6(5) . . . . ? N1 C5 C12 C11 -1.4(5) . . . . ? C2 C1 C12 C5 1.1(6) . . . . ? C2 C1 C12 C11 -177.8(5) . . . . ? C10 C11 C12 C5 -177.9(5) . . . . ? C6 C11 C12 C5 0.4(5) . . . . ? C10 C11 C12 C1 1.2(10) . . . . ? C6 C11 C12 C1 179.4(4) . . . . ? C1 C2 C14 C15 5.2(7) . . . . ? C3 C2 C14 C15 -174.6(5) . . . . ? C2 C14 C15 C16 -177.4(5) . . . . ? C14 C15 C16 C17 -4.7(8) . . . . ? C14 C15 C16 C20 174.0(5) . . . . ? C20 C16 C17 C18 -1.3(7) . . . . ? C15 C16 C17 C18 177.4(4) . . . . ? C16 C17 C18 N2 0.3(8) . . . . ? C19 N2 C18 C17 0.9(7) . . . . ? C21 N2 C18 C17 177.9(5) . . . . ? C18 N2 C19 C20 -1.2(7) . . . . ? C21 N2 C19 C20 -178.1(4) . . . . ? N2 C19 C20 C16 0.1(7) . . . . ? C17 C16 C20 C19 1.1(7) . . . . ? C15 C16 C20 C19 -177.7(4) . . . . ? O2 S1 C22 C27 169.0(4) . . . . ? O1 S1 C22 C27 -68.8(4) . . . . ? O3 S1 C22 C27 49.7(4) . . . . ? O2 S1 C22 C23 -11.8(5) . . . . ? O1 S1 C22 C23 110.4(4) . . . . ? O3 S1 C22 C23 -131.1(4) . . . . ? C27 C22 C23 C24 -0.5(7) . . . . ? S1 C22 C23 C24 -179.7(4) . . . . ? C22 C23 C24 C25 1.2(7) . . . . ? C23 C24 C25 C26 -1.2(7) . . . . ? C23 C24 C25 C28 -178.9(5) . . . . ? C24 C25 C26 C27 0.4(7) . . . . ? C28 C25 C26 C27 178.2(4) . . . . ? C25 C26 C27 C22 0.2(7) . . . . ? C23 C22 C27 C26 -0.2(7) . . . . ? S1 C22 C27 C26 179.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.40 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.236 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.058