Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_shelxl _database_code_CSD 171458 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Suzuki, Masato' 'Yatsugi, Yutaka' _publ_contact_author_name 'Prof Masato Suzuki' _publ_contact_author_address ; Organic and Polymeric Materials Tokyo Institute of Technology O-okayama 2-12-1 Meguro-ku Tokyo 152-8552 JAPAN ; _publ_contact_author_email 'MSUZUKI@POLYMER.TITECH.AC.JP' _publ_section_title ; Novel Solid-State Polycondensation I. Oxidative-Coupling Polymerization of 2,6-Dihydroxynaphthalene ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-Dihydroxynaphthalene-Benzylamine 1:2 Complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 N2 O2' _chemical_formula_weight 374.47 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 monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.6490(6) _cell_length_b 13.7087(17) _cell_length_c 9.7362(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.118(2) _cell_angle_gamma 90.00 _cell_volume 980.79(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prizm _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-run _exptl_absorpt_correction_T_min 0.9723 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku UX-18 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS 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 8037 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2232 _reflns_number_gt 1933 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID AUTO' _computing_cell_refinement 'RAPID SCALE' _computing_data_reduction 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0511P)^2^+0.4460P] 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 0.037(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2232 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 O1 O 1.59156(15) 0.32130(9) 0.90842(13) 0.0381(3) Uani 1 1 d . . . H1C H 1.476(3) 0.3414(16) 0.856(2) 0.057 Uiso 1 1 d . . . N1 N 1.24474(18) 0.36360(13) 0.76095(15) 0.0370(3) Uani 1 1 d . . . H1A H 1.214(3) 0.4178(16) 0.803(2) 0.044 Uiso 1 1 d . . . H1B H 1.190(3) 0.3120(15) 0.790(2) 0.044 Uiso 1 1 d . . . C1 C 0.98086(19) 0.37322(10) 0.53756(15) 0.0261(3) Uani 1 1 d . . . C2 C 0.8568(2) 0.39036(12) 0.61636(16) 0.0302(3) Uani 1 1 d . . . H2 H 0.899(2) 0.4038(13) 0.715(2) 0.036 Uiso 1 1 d . . . C3 C 0.6707(2) 0.39000(12) 0.55107(18) 0.0344(4) Uani 1 1 d . . . H3 H 0.587(3) 0.4033(14) 0.606(2) 0.041 Uiso 1 1 d . . . C4 C 0.6057(2) 0.37244(12) 0.40648(17) 0.0332(4) Uani 1 1 d . . . H4 H 0.472(3) 0.3726(13) 0.360(2) 0.040 Uiso 1 1 d . . . C5 C 0.7282(2) 0.35612(12) 0.32612(17) 0.0348(4) Uani 1 1 d . . . H5 H 0.685(3) 0.3452(14) 0.226(2) 0.042 Uiso 1 1 d . . . C6 C 0.9137(2) 0.35713(12) 0.39135(17) 0.0318(4) Uani 1 1 d . . . H6 H 1.000(3) 0.3461(14) 0.337(2) 0.038 Uiso 1 1 d . . . C7 C 1.18470(19) 0.37308(12) 0.60559(17) 0.0294(3) Uani 1 1 d . . . H7A H 1.239(2) 0.3193(14) 0.5646(19) 0.035 Uiso 1 1 d . . . H7B H 1.235(2) 0.4358(13) 0.5794(19) 0.035 Uiso 1 1 d . . . C8 C 1.97291(19) 0.54833(11) 0.97741(14) 0.0278(3) Uani 1 1 d . . . C9 C 1.7867(2) 0.56732(12) 0.91296(17) 0.0315(4) Uani 1 1 d . . . H9 H 1.754(2) 0.6376(14) 0.886(2) 0.038 Uiso 1 1 d . . . C10 C 1.6608(2) 0.49359(12) 0.89262(16) 0.0326(4) Uani 1 1 d . . . H10 H 1.530(3) 0.5084(14) 0.844(2) 0.039 Uiso 1 1 d . . . C11 C 1.71458(19) 0.39600(12) 0.93391(15) 0.0299(3) Uani 1 1 d . . . C12 C 1.8931(2) 0.37574(12) 0.99902(16) 0.0313(3) Uani 1 1 d . . . H12 H 1.929(2) 0.3103(14) 1.0263(19) 0.038 Uiso 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 O1 0.0216(5) 0.0406(7) 0.0465(7) 0.0031(5) 0.0004(5) -0.0044(5) N1 0.0225(6) 0.0519(9) 0.0339(7) 0.0023(6) 0.0034(5) -0.0021(6) C1 0.0238(7) 0.0242(7) 0.0291(7) 0.0011(5) 0.0051(5) -0.0009(5) C2 0.0244(7) 0.0383(8) 0.0266(7) 0.0005(6) 0.0046(5) -0.0021(6) C3 0.0244(7) 0.0425(9) 0.0362(8) 0.0041(7) 0.0085(6) -0.0002(6) C4 0.0246(7) 0.0327(8) 0.0368(8) 0.0050(6) -0.0007(6) -0.0019(6) C5 0.0376(8) 0.0342(8) 0.0273(8) -0.0011(6) 0.0000(6) 0.0017(6) C6 0.0323(8) 0.0331(8) 0.0302(8) -0.0002(6) 0.0087(6) 0.0044(6) C7 0.0214(7) 0.0326(8) 0.0337(8) -0.0003(6) 0.0070(6) -0.0006(6) C8 0.0252(7) 0.0371(8) 0.0199(6) -0.0013(6) 0.0042(5) 0.0058(6) C9 0.0254(7) 0.0355(8) 0.0305(8) 0.0007(6) 0.0027(6) 0.0060(6) C10 0.0231(7) 0.0439(9) 0.0288(7) -0.0010(6) 0.0040(5) 0.0038(6) C11 0.0235(7) 0.0407(8) 0.0253(7) -0.0030(6) 0.0063(5) -0.0035(6) C12 0.0273(7) 0.0380(9) 0.0268(7) 0.0002(6) 0.0045(6) 0.0022(6) _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 O1 C11 1.3660(18) . y O1 H1C 0.93(2) . ? N1 C7 1.459(2) . y N1 H1A 0.91(2) . ? N1 H1B 0.91(2) . ? C1 C6 1.390(2) . y C1 C2 1.396(2) . y C1 C7 1.5154(19) . y C2 C3 1.389(2) . y C2 H2 0.945(19) . ? C3 C4 1.378(2) . y C3 H3 0.95(2) . ? C4 C5 1.395(2) . y C4 H4 0.995(19) . ? C5 C6 1.384(2) . y C5 H5 0.95(2) . ? C6 H6 0.965(19) . ? C7 H7A 0.984(19) . ? C7 H7B 1.002(19) . ? C8 C9 1.4123(19) . y C8 C8 1.421(3) 3_967 y C8 C12 1.434(2) 3_967 y C9 C10 1.372(2) . y C9 H9 1.012(19) . ? C10 C11 1.424(2) . y C10 H10 1.004(19) . ? C11 C12 1.365(2) . y C12 C8 1.434(2) 3_967 y C12 H12 0.954(19) . ? 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 C11 O1 H1C 112.2(14) . . ? C7 N1 H1A 110.4(13) . . ? C7 N1 H1B 110.7(13) . . ? H1A N1 H1B 107.1(18) . . ? C6 C1 C2 118.36(13) . . y C6 C1 C7 119.36(13) . . y C2 C1 C7 122.28(13) . . y C3 C2 C1 120.98(14) . . y C3 C2 H2 119.0(11) . . ? C1 C2 H2 120.0(11) . . ? C4 C3 C2 120.09(15) . . y C4 C3 H3 119.7(12) . . ? C2 C3 H3 120.2(12) . . ? C3 C4 C5 119.55(14) . . y C3 C4 H4 119.6(11) . . ? C5 C4 H4 120.8(11) . . ? C6 C5 C4 120.23(14) . . y C6 C5 H5 119.7(12) . . ? C4 C5 H5 120.1(12) . . ? C5 C6 C1 120.78(14) . . y C5 C6 H6 121.0(11) . . ? C1 C6 H6 118.2(11) . . ? N1 C7 C1 116.27(12) . . y N1 C7 H7A 107.8(11) . . ? C1 C7 H7A 108.9(11) . . ? N1 C7 H7B 107.9(11) . . ? C1 C7 H7B 107.8(10) . . ? H7A C7 H7B 107.9(14) . . ? C9 C8 C8 118.75(17) . 3_967 y C9 C8 C12 121.69(14) . 3_967 y C8 C8 C12 119.55(16) 3_967 3_967 y C10 C9 C8 120.61(14) . . y C10 C9 H9 123.3(11) . . ? C8 C9 H9 116.1(11) . . ? C9 C10 C11 121.03(14) . . y C9 C10 H10 119.3(11) . . ? C11 C10 H10 119.7(11) . . ? C12 C11 O1 118.80(15) . . y C12 C11 C10 119.69(14) . . y O1 C11 C10 121.51(13) . . y C11 C12 C8 120.34(15) . 3_967 y C11 C12 H12 119.6(11) . . ? C8 C12 H12 120.0(11) 3_967 . ? 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 C6 C1 C2 C3 0.9(2) . . . . ? C7 C1 C2 C3 -179.98(15) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C1 0.7(2) . . . . ? C2 C1 C6 C5 -1.3(2) . . . . ? C7 C1 C6 C5 179.55(14) . . . . ? C6 C1 C7 N1 -163.80(15) . . . . ? C2 C1 C7 N1 17.1(2) . . . . ? C8 C8 C9 C10 -0.9(3) 3_967 . . . ? C12 C8 C9 C10 -179.46(14) 3_967 . . . ? C8 C9 C10 C11 -0.9(2) . . . . ? C9 C10 C11 C12 2.2(2) . . . . ? C9 C10 C11 O1 -177.06(14) . . . . ? O1 C11 C12 C8 177.63(13) . . . 3_967 ? C10 C11 C12 C8 -1.6(2) . . . 3_967 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B O1 0.91(2) 2.39(2) 3.285(2) 168.9(17) 4_565 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.376 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.040