Supplementary Material (ESI) for J. Mater. Chem. This journal is (C) The Royal Society of Chemistry 2002 data_s92 _database_code_CSD 186196 _journal_coden_Cambridge 1145 _publ_requested_journal 'Journal of Materials Chemistry' loop_ _publ_author_name 'Bruce, Duncan' 'Coles, Simon' 'Donnio, Bertrand' 'Huck, Deborah M.' 'Hursthouse, M.' 'Nguyen, H. Loc' _publ_contact_author_name 'Prof Duncan Bruce' _publ_contact_author_address ; School of Chemistry University of Exeter Stocker Road EXETER EX4 4QD UNITED KINGDOM ; _publ_contact_author_email 'D.BRUCE@EX.AC.UK' _publ_section_title ; Mesomorphic Silver(I) Complexes of 4-Alkyloxy-2'-stilbazoles and 4-Alkyloxy-3'-stilbazoles. Crystal and Molecular Structure of 4-Methoxy-2'-stilbazole. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N O' _chemical_formula_weight 211.25 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 9.2463(18) _cell_length_b 33.461(7) _cell_length_c 7.2285(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2236.4(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8553 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9541 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\\f and \\w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7063 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2481 _reflns_number_gt 2017 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _computing_publication_material ? _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^)+(0.0969P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(19) _refine_ls_number_reflns 2481 _refine_ls_number_parameters 147 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1471 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 C1 C 0.8144(3) 0.53740(7) 1.5788(3) 0.0461(6) Uani 1 1 d . . . H1A H 0.8201 0.5642 1.6326 0.069 Uiso 1 1 calc R . . H1B H 0.9095 0.5297 1.5307 0.069 Uiso 1 1 calc R . . H1C H 0.7843 0.5183 1.6741 0.069 Uiso 1 1 calc R . . C2 C 0.7348(2) 0.56362(6) 1.2893(3) 0.0290(5) Uani 1 1 d . . . C3 C 0.8481(2) 0.59083(6) 1.2827(3) 0.0292(5) Uani 1 1 d . . . H3 H 0.9168 0.5921 1.3803 0.035 Uiso 1 1 calc R . . C4 C 0.8596(2) 0.61626(6) 1.1307(3) 0.0276(5) Uani 1 1 d . . . H4 H 0.9366 0.6350 1.1270 0.033 Uiso 1 1 calc R . . C5 C 0.7626(2) 0.61513(6) 0.9849(3) 0.0264(5) Uani 1 1 d . . . C6 C 0.6491(2) 0.58705(6) 0.9952(3) 0.0305(5) Uani 1 1 d . . . H6 H 0.5804 0.5856 0.8978 0.037 Uiso 1 1 calc R . . C7 C 0.6364(2) 0.56169(6) 1.1444(3) 0.0317(5) Uani 1 1 d . . . H7 H 0.5598 0.5428 1.1482 0.038 Uiso 1 1 calc R . . C8 C 0.7827(2) 0.64231(6) 0.8289(3) 0.0264(5) Uani 1 1 d . . . H8 H 0.8626 0.6601 0.8371 0.032 Uiso 1 1 calc R . . C9 C 0.7025(2) 0.64512(6) 0.6767(3) 0.0275(5) Uani 1 1 d . . . H9 H 0.6204 0.6282 0.6664 0.033 Uiso 1 1 calc R . . C10 C 0.7329(2) 0.67269(6) 0.5236(3) 0.0264(5) Uani 1 1 d . . . C11 C 0.8912(2) 0.71546(6) 0.3791(3) 0.0309(5) Uani 1 1 d . . . H11 H 0.9835 0.7278 0.3745 0.037 Uiso 1 1 calc R . . C12 C 0.7937(2) 0.72462(6) 0.2417(3) 0.0343(5) Uani 1 1 d . . . H12 H 0.8179 0.7429 0.1461 0.041 Uiso 1 1 calc R . . C13 C 0.6603(3) 0.70655(7) 0.2465(3) 0.0362(6) Uani 1 1 d . . . H13 H 0.5904 0.7122 0.1538 0.043 Uiso 1 1 calc R . . C14 C 0.6291(2) 0.68008(6) 0.3879(3) 0.0317(5) Uani 1 1 d . . . H14 H 0.5378 0.6671 0.3926 0.038 Uiso 1 1 calc R . . N1 N 0.86453(18) 0.69026(5) 0.5191(2) 0.0283(4) Uani 1 1 d . . . O1 O 0.71173(18) 0.53731(4) 1.4319(2) 0.0397(5) Uani 1 1 d . . . 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 C1 0.0724(17) 0.0248(12) 0.0411(13) 0.0088(10) -0.0055(13) -0.0011(12) C2 0.0411(12) 0.0167(9) 0.0292(11) -0.0008(8) 0.0062(10) 0.0026(8) C3 0.0391(11) 0.0220(9) 0.0266(10) -0.0027(8) 0.0009(9) 0.0015(8) C4 0.0346(11) 0.0183(9) 0.0299(11) -0.0034(8) 0.0033(9) -0.0016(8) C5 0.0313(10) 0.0178(9) 0.0301(11) -0.0040(8) 0.0047(9) -0.0002(8) C6 0.0339(11) 0.0242(10) 0.0332(11) -0.0041(9) -0.0001(9) -0.0024(8) C7 0.0369(12) 0.0211(10) 0.0372(12) -0.0029(9) 0.0057(10) -0.0063(8) C8 0.0309(10) 0.0174(9) 0.0309(11) -0.0014(8) 0.0041(8) -0.0003(8) C9 0.0306(11) 0.0203(10) 0.0317(11) -0.0041(8) 0.0024(9) -0.0007(8) C10 0.0331(11) 0.0182(9) 0.0280(10) -0.0062(8) 0.0018(9) 0.0054(8) C11 0.0368(12) 0.0207(10) 0.0351(11) 0.0008(9) 0.0039(10) 0.0017(8) C12 0.0478(13) 0.0235(10) 0.0316(11) 0.0029(9) 0.0028(10) 0.0098(9) C13 0.0466(13) 0.0322(11) 0.0299(12) -0.0016(10) -0.0077(11) 0.0123(10) C14 0.0346(11) 0.0259(10) 0.0347(11) -0.0063(9) -0.0027(9) 0.0023(9) N1 0.0346(10) 0.0206(8) 0.0297(9) 0.0002(7) 0.0014(8) 0.0026(7) O1 0.0580(10) 0.0253(8) 0.0357(8) 0.0049(7) 0.0017(8) -0.0062(7) _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 C1 O1 1.424(3) . ? C2 O1 1.372(2) . ? C2 C7 1.389(3) . ? C2 C3 1.389(3) . ? C3 C4 1.394(3) . ? C4 C5 1.384(3) . ? C5 C6 1.411(3) . ? C5 C8 1.461(3) . ? C6 C7 1.377(3) . ? C8 C9 1.330(3) . ? C9 C10 1.468(3) . ? C10 N1 1.352(3) . ? C10 C14 1.394(3) . ? C11 N1 1.340(3) . ? C11 C12 1.376(3) . ? C12 C13 1.374(3) . ? C13 C14 1.383(3) . ? 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 O1 C2 C7 115.76(17) . . ? O1 C2 C3 124.31(19) . . ? C7 C2 C3 119.93(18) . . ? C2 C3 C4 118.97(19) . . ? C5 C4 C3 122.32(18) . . ? C4 C5 C6 117.36(19) . . ? C4 C5 C8 119.24(18) . . ? C6 C5 C8 123.39(19) . . ? C7 C6 C5 121.1(2) . . ? C6 C7 C2 120.36(18) . . ? C9 C8 C5 127.71(18) . . ? C8 C9 C10 124.14(18) . . ? N1 C10 C14 121.72(19) . . ? N1 C10 C9 117.62(19) . . ? C14 C10 C9 120.66(18) . . ? N1 C11 C12 124.4(2) . . ? C13 C12 C11 118.1(2) . . ? C12 C13 C14 119.2(2) . . ? C13 C14 C10 119.3(2) . . ? C11 N1 C10 117.20(18) . . ? C2 O1 C1 117.06(18) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.209 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.053