Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Deqing Zhang' _publ_contact_author_address ; Organic Solids Laboratory Institute of Chemistry, CAS Beijing 100080 CHINA ; _publ_contact_author_email DQZHANG@ICCAS.AC.CN _publ_section_title ; 4-(N, N-dimethylamine)benzonitrile (DMABN) derivatives with boronic acid and boronate groups: new fluorescent sensors for saccharides and fluoride ion ; loop_ _publ_author_name 'Deqing Zhang.' 'Wei Tan.' 'Zhuo Wang.' 'Daoben Zhu.' data_sad _database_code_depnum_ccdc_archive 'CCDC 629770' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 B N2 O2' _chemical_formula_weight 272.15 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0000 '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 7.3178(14) _cell_length_b 10.551(2) _cell_length_c 20.587(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1589.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1355 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 19.04 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9852 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details 'sadabs(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8938 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1637 _reflns_number_gt 1279 _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^)+(0.0759P)^2^+0.5656P] 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 ? _refine_ls_number_reflns 1637 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1570 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 N1 N 0.0437(8) -0.1592(5) 0.0974(2) 0.0835(15) Uani 1 1 d . . . N2 N 0.8502(7) 0.0951(5) 0.00612(19) 0.0761(13) Uani 1 1 d . . . O1 O 0.2255(5) 0.0415(3) 0.20610(14) 0.0654(10) Uani 1 1 d . . . O2 O 0.4238(5) 0.2015(4) 0.19671(16) 0.0813(12) Uani 1 1 d . . . B1 B 0.3585(7) 0.0932(5) 0.1710(2) 0.0475(12) Uani 1 1 d . . . C1 C 0.4380(6) 0.0385(4) 0.10533(18) 0.0488(11) Uani 1 1 d . . . C2 C 0.3531(7) -0.0572(4) 0.06892(19) 0.0518(11) Uani 1 1 d . . . C3 C 0.4364(8) -0.1013(5) 0.0129(2) 0.0634(14) Uani 1 1 d . . . H3A H 0.3800 -0.1650 -0.0110 0.076 Uiso 1 1 calc R . . C4 C 0.5994(8) -0.0533(5) -0.0080(2) 0.0690(15) Uani 1 1 d . . . H4A H 0.6521 -0.0852 -0.0457 0.083 Uiso 1 1 calc R . . C5 C 0.6902(7) 0.0446(4) 0.02690(19) 0.0559(12) Uani 1 1 d . . . C6 C 0.6026(7) 0.0858(4) 0.08404(19) 0.0538(12) Uani 1 1 d . . . H6A H 0.6591 0.1483 0.1087 0.065 Uiso 1 1 calc R . . C7 C 0.1811(9) -0.1120(5) 0.0865(2) 0.0602(13) Uani 1 1 d . . . C8 C 0.9488(9) 0.1829(6) 0.0460(3) 0.0884(18) Uani 1 1 d . . . H8A H 0.8764 0.2577 0.0525 0.133 Uiso 1 1 calc R . . H8B H 1.0613 0.2054 0.0250 0.133 Uiso 1 1 calc R . . H8C H 0.9748 0.1445 0.0872 0.133 Uiso 1 1 calc R . . C9 C 0.9393(10) 0.0501(7) -0.0520(3) 0.106(2) Uani 1 1 d . . . H9A H 0.9687 -0.0381 -0.0471 0.159 Uiso 1 1 calc R . . H9B H 1.0495 0.0975 -0.0591 0.159 Uiso 1 1 calc R . . H9C H 0.8591 0.0609 -0.0885 0.159 Uiso 1 1 calc R . . C10 C 0.3430(6) 0.2204(4) 0.2597(2) 0.0530(11) Uani 1 1 d . . . C11 C 0.4894(9) 0.1924(7) 0.3087(3) 0.101(2) Uani 1 1 d . . . H11C H 0.5837 0.2554 0.3057 0.152 Uiso 1 1 calc R . . H11D H 0.5404 0.1102 0.3003 0.152 Uiso 1 1 calc R . . H11A H 0.4376 0.1938 0.3516 0.152 Uiso 1 1 calc R . . C12 C 0.2889(9) 0.3576(5) 0.2658(3) 0.094(2) Uani 1 1 d . . . H12A H 0.3965 0.4096 0.2658 0.141 Uiso 1 1 calc R . . H12B H 0.2233 0.3699 0.3057 0.141 Uiso 1 1 calc R . . H12C H 0.2123 0.3808 0.2299 0.141 Uiso 1 1 calc R . . C13 C 0.1806(7) 0.1256(5) 0.2590(2) 0.0583(13) Uani 1 1 d . . . C14 C 0.1644(13) 0.0487(7) 0.3204(3) 0.125(3) Uani 1 1 d . . . H14A H 0.0619 -0.0077 0.3170 0.187 Uiso 1 1 calc R . . H14C H 0.1468 0.1046 0.3567 0.187 Uiso 1 1 calc R . . H14D H 0.2741 0.0004 0.3267 0.187 Uiso 1 1 calc R . . C15 C 0.0002(8) 0.1860(8) 0.2408(4) 0.117(3) Uani 1 1 d . . . H15A H -0.0943 0.1229 0.2413 0.175 Uiso 1 1 calc R . . H15B H 0.0092 0.2220 0.1981 0.175 Uiso 1 1 calc R . . H15C H -0.0287 0.2516 0.2715 0.175 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 N1 0.099(4) 0.077(3) 0.074(3) -0.015(2) 0.007(3) -0.026(3) N2 0.081(3) 0.088(3) 0.059(2) -0.001(2) 0.023(2) -0.005(3) O1 0.083(2) 0.057(2) 0.0564(17) -0.0213(16) 0.0202(17) -0.020(2) O2 0.085(3) 0.090(3) 0.069(2) -0.035(2) 0.0303(19) -0.043(2) B1 0.059(3) 0.041(3) 0.043(2) 0.005(2) -0.003(2) 0.000(3) C1 0.062(3) 0.045(2) 0.040(2) 0.001(2) -0.002(2) 0.011(2) C2 0.065(3) 0.047(2) 0.043(2) 0.000(2) 0.000(2) 0.003(2) C3 0.088(4) 0.058(3) 0.045(2) -0.008(2) -0.005(3) 0.005(3) C4 0.090(4) 0.071(3) 0.046(2) -0.010(3) 0.013(3) 0.014(3) C5 0.069(3) 0.057(3) 0.041(2) 0.007(2) 0.007(2) 0.014(3) C6 0.066(3) 0.049(3) 0.046(2) -0.004(2) 0.002(2) 0.003(2) C7 0.085(4) 0.053(3) 0.042(2) -0.012(2) -0.002(3) -0.001(3) C8 0.077(4) 0.099(4) 0.089(4) 0.014(4) 0.018(3) -0.003(4) C9 0.109(5) 0.134(6) 0.074(3) -0.003(4) 0.043(4) 0.002(5) C10 0.054(3) 0.056(3) 0.049(2) -0.017(2) 0.005(2) -0.003(2) C11 0.091(5) 0.123(6) 0.089(4) -0.016(4) -0.030(4) -0.006(4) C12 0.104(5) 0.058(3) 0.121(5) -0.008(3) 0.024(4) -0.004(3) C13 0.059(3) 0.068(3) 0.049(2) -0.021(2) 0.013(2) -0.015(3) C14 0.182(8) 0.121(6) 0.071(3) -0.003(4) 0.024(4) -0.078(6) C15 0.058(3) 0.140(6) 0.152(6) -0.069(6) -0.003(4) 0.001(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 N1 C7 1.144(7) . ? N2 C5 1.356(7) . ? N2 C8 1.433(7) . ? N2 C9 1.443(6) . ? O1 B1 1.330(6) . ? O1 C13 1.443(5) . ? O2 B1 1.348(6) . ? O2 C10 1.439(5) . ? B1 C1 1.580(6) . ? C1 C6 1.375(6) . ? C1 C2 1.403(6) . ? C2 C3 1.384(6) . ? C2 C7 1.432(8) . ? C3 C4 1.366(8) . ? C3 H3A 0.9300 . ? C4 C5 1.422(7) . ? C4 H4A 0.9300 . ? C5 C6 1.408(6) . ? C6 H6A 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.501(7) . ? C10 C12 1.506(7) . ? C10 C13 1.553(6) . ? C11 H11C 0.9600 . ? C11 H11D 0.9600 . ? C11 H11A 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.507(7) . ? C13 C15 1.513(8) . ? C14 H14A 0.9600 . ? C14 H14C 0.9600 . ? C14 H14D 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 C5 N2 C8 120.6(4) . . ? C5 N2 C9 121.5(5) . . ? C8 N2 C9 117.4(5) . . ? B1 O1 C13 109.0(3) . . ? B1 O2 C10 109.0(3) . . ? O1 B1 O2 113.2(4) . . ? O1 B1 C1 125.8(4) . . ? O2 B1 C1 121.0(4) . . ? C6 C1 C2 118.6(4) . . ? C6 C1 B1 117.6(4) . . ? C2 C1 B1 123.8(4) . . ? C3 C2 C1 119.5(5) . . ? C3 C2 C7 117.5(4) . . ? C1 C2 C7 123.0(4) . . ? C4 C3 C2 121.5(5) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 121.2(4) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? N2 C5 C6 122.3(5) . . ? N2 C5 C4 122.0(4) . . ? C6 C5 C4 115.7(5) . . ? C1 C6 C5 123.6(4) . . ? C1 C6 H6A 118.2 . . ? C5 C6 H6A 118.2 . . ? N1 C7 C2 176.3(5) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C11 106.6(4) . . ? O2 C10 C12 108.5(4) . . ? C11 C10 C12 108.7(5) . . ? O2 C10 C13 102.5(3) . . ? C11 C10 C13 115.2(4) . . ? C12 C10 C13 114.7(4) . . ? C10 C11 H11C 109.5 . . ? C10 C11 H11D 109.5 . . ? H11C C11 H11D 109.5 . . ? C10 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11D C11 H11A 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 C14 108.7(4) . . ? O1 C13 C15 105.7(4) . . ? C14 C13 C15 111.5(6) . . ? O1 C13 C10 103.2(3) . . ? C14 C13 C10 113.5(4) . . ? C15 C13 C10 113.5(5) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? C13 C14 H14D 109.5 . . ? H14A C14 H14D 109.5 . . ? H14C C14 H14D 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.181 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.039