data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Jin-Pei Cheng.' 'Jiaqi He.' 'Xueliang Jiang.' 'Hao-Tao Niu.' 'Dongdong Su.' 'Wenzhi Yang.' 'Zhenming Yin.' _publ_contact_author_name 'Jin-Pei Cheng' _publ_contact_author_email CHENGJP@NANKAI.EDU.CN _publ_section_title ; A simple yet highly selective colorimetric sensor for cyanide anion in aqueous environment ; # Attachment 'r80426c.cif' data_r80426c _database_code_depnum_ccdc_archive 'CCDC 688682' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 F3 N O4 S' _chemical_formula_weight 397.36 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' F F 0.0171 0.0103 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5833(17) _cell_length_b 10.109(2) _cell_length_c 10.778(2) _cell_angle_alpha 106.89(3) _cell_angle_beta 92.62(3) _cell_angle_gamma 108.79(3) _cell_volume 837.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2620 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.9 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9609 _exptl_absorpt_correction_T_max 0.9753 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5992 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3883 _reflns_number_gt 2910 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0658P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3883 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.36313(5) 0.53578(4) 0.82602(4) 0.02267(12) Uani 1 1 d . . . F1 F 0.15492(11) -0.31890(11) 0.57251(10) 0.0312(2) Uani 1 1 d . . . F2 F 0.34739(12) -0.29929(10) 0.45218(10) 0.0327(2) Uani 1 1 d . . . F3 F 0.16831(13) -0.19569(11) 0.43923(10) 0.0386(3) Uani 1 1 d . . . O1 O 1.08144(13) 0.41077(11) 1.10996(11) 0.0244(3) Uani 1 1 d . . . O2 O 0.78102(13) -0.15045(11) 1.09565(11) 0.0251(3) Uani 1 1 d . . . O3 O 0.38599(14) 0.03390(12) 0.61552(12) 0.0277(3) Uani 1 1 d . . . O4 O 0.40768(14) 0.60258(12) 0.71856(12) 0.0295(3) Uani 1 1 d . . . N1 N 0.45589(14) -0.11076(14) 0.72179(12) 0.0174(3) Uani 1 1 d . . . H1A H 0.442(2) -0.196(2) 0.7209(17) 0.021 Uiso 1 1 d . . . C1 C 0.66050(17) 0.14203(16) 0.82644(14) 0.0174(3) Uani 1 1 d . . . H1 H 0.6182 0.1779 0.7651 0.021 Uiso 1 1 calc R . . C2 C 0.79480(17) 0.23522(15) 0.92178(15) 0.0172(3) Uani 1 1 d . . . H2 H 0.8453 0.3348 0.9246 0.021 Uiso 1 1 calc R . . C3 C 0.85774(16) 0.18589(15) 1.01418(14) 0.0144(3) Uani 1 1 d . . . C4 C 1.00638(17) 0.28609(15) 1.11149(14) 0.0157(3) Uani 1 1 d . . . C5 C 1.06153(16) 0.23055(15) 1.21305(14) 0.0151(3) Uani 1 1 d . . . C6 C 1.19365(17) 0.32508(16) 1.31132(15) 0.0193(3) Uani 1 1 d . . . H6 H 1.2473 0.4240 1.3133 0.023 Uiso 1 1 calc R . . C7 C 1.24775(18) 0.27577(17) 1.40666(15) 0.0222(3) Uani 1 1 d . . . H7 H 1.3382 0.3409 1.4738 0.027 Uiso 1 1 calc R . . C8 C 1.16973(18) 0.13136(18) 1.40399(15) 0.0224(3) Uani 1 1 d . . . H8 H 1.2073 0.0977 1.4692 0.027 Uiso 1 1 calc R . . C9 C 1.03743(17) 0.03602(16) 1.30671(15) 0.0189(3) Uani 1 1 d . . . H9 H 0.9841 -0.0626 1.3057 0.023 Uiso 1 1 calc R . . C10 C 0.98233(16) 0.08442(15) 1.21022(14) 0.0154(3) Uani 1 1 d . . . C11 C 0.84274(17) -0.01969(15) 1.10555(14) 0.0157(3) Uani 1 1 d . . . C12 C 0.78026(16) 0.03914(15) 1.00927(13) 0.0142(3) Uani 1 1 d . . . C13 C 0.64647(16) -0.05527(15) 0.91370(14) 0.0151(3) Uani 1 1 d . . . H13 H 0.5949 -0.1545 0.9116 0.018 Uiso 1 1 calc R . . C14 C 0.58665(16) -0.00547(16) 0.82018(14) 0.0154(3) Uani 1 1 d . . . C15 C 0.37487(17) -0.08411(16) 0.62683(14) 0.0179(3) Uani 1 1 d . . . C16 C 0.25922(18) -0.22648(17) 0.52227(15) 0.0206(3) Uani 1 1 d . . . C17 C 0.47721(19) 0.41535(19) 0.81710(17) 0.0273(4) Uani 1 1 d . . . H17A H 0.4592 0.3496 0.7266 0.041 Uiso 1 1 calc R . . H17B H 0.4392 0.3564 0.8750 0.041 Uiso 1 1 calc R . . H17C H 0.5961 0.4736 0.8447 0.041 Uiso 1 1 calc R . . C18 C 0.16154(19) 0.39779(18) 0.76733(19) 0.0285(4) Uani 1 1 d . . . H18A H 0.0801 0.4446 0.7575 0.043 Uiso 1 1 calc R . . H18B H 0.1312 0.3439 0.8301 0.043 Uiso 1 1 calc R . . H18C H 0.1624 0.3289 0.6821 0.043 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 0.0248(2) 0.01534(19) 0.0241(2) 0.00392(16) 0.00111(15) 0.00478(15) F1 0.0231(5) 0.0305(5) 0.0286(5) 0.0076(5) 0.0035(4) -0.0036(4) F2 0.0284(5) 0.0275(5) 0.0303(6) -0.0048(4) 0.0078(4) 0.0066(4) F3 0.0414(6) 0.0330(6) 0.0318(6) 0.0064(5) -0.0211(5) 0.0077(5) O1 0.0246(6) 0.0131(5) 0.0308(6) 0.0085(5) -0.0035(5) 0.0000(4) O2 0.0272(6) 0.0153(5) 0.0284(6) 0.0106(5) -0.0045(5) -0.0002(4) O3 0.0320(6) 0.0202(6) 0.0285(6) 0.0072(5) -0.0094(5) 0.0084(5) O4 0.0299(6) 0.0187(6) 0.0398(7) 0.0161(6) 0.0005(5) 0.0030(5) N1 0.0180(6) 0.0143(6) 0.0173(6) 0.0053(5) -0.0029(5) 0.0029(5) C1 0.0191(7) 0.0168(7) 0.0185(7) 0.0076(6) 0.0016(5) 0.0075(5) C2 0.0190(7) 0.0122(6) 0.0216(7) 0.0068(6) 0.0036(6) 0.0059(5) C3 0.0138(6) 0.0123(6) 0.0161(7) 0.0035(6) 0.0024(5) 0.0041(5) C4 0.0152(6) 0.0125(6) 0.0180(7) 0.0032(6) 0.0020(5) 0.0047(5) C5 0.0144(6) 0.0138(6) 0.0158(7) 0.0031(6) 0.0021(5) 0.0049(5) C6 0.0175(7) 0.0164(7) 0.0199(8) 0.0034(6) 0.0022(6) 0.0029(5) C7 0.0174(7) 0.0248(8) 0.0184(8) 0.0030(7) -0.0023(6) 0.0039(6) C8 0.0228(7) 0.0271(8) 0.0182(8) 0.0079(7) 0.0001(6) 0.0098(6) C9 0.0205(7) 0.0172(7) 0.0190(7) 0.0066(6) 0.0015(6) 0.0060(6) C10 0.0141(6) 0.0157(7) 0.0154(7) 0.0043(6) 0.0023(5) 0.0044(5) C11 0.0153(6) 0.0146(7) 0.0162(7) 0.0051(6) 0.0018(5) 0.0041(5) C12 0.0141(6) 0.0138(6) 0.0156(7) 0.0055(6) 0.0036(5) 0.0052(5) C13 0.0154(6) 0.0126(6) 0.0165(7) 0.0049(6) 0.0025(5) 0.0036(5) C14 0.0138(6) 0.0166(7) 0.0153(7) 0.0043(6) 0.0021(5) 0.0055(5) C15 0.0158(7) 0.0210(7) 0.0168(7) 0.0050(6) 0.0015(5) 0.0072(6) C16 0.0187(7) 0.0226(7) 0.0187(7) 0.0060(6) 0.0006(6) 0.0060(6) C17 0.0241(8) 0.0290(8) 0.0342(9) 0.0175(8) 0.0056(7) 0.0099(7) C18 0.0201(8) 0.0206(8) 0.0436(10) 0.0113(8) 0.0065(7) 0.0046(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 S1 O4 1.5074(12) . ? S1 C17 1.7773(16) . ? S1 C18 1.7811(18) . ? F1 C16 1.3293(17) . ? F2 C16 1.3316(18) . ? F3 C16 1.3272(17) . ? O1 C4 1.2223(16) . ? O2 C11 1.2252(17) . ? O3 C15 1.2081(17) . ? N1 C15 1.3489(17) . ? N1 C14 1.408(2) . ? N1 H1A 0.832(17) . ? C1 C2 1.379(2) . ? C1 C14 1.3994(19) . ? C1 H1 0.9500 . ? C2 C3 1.3947(18) . ? C2 H2 0.9500 . ? C3 C12 1.4006(18) . ? C3 C4 1.477(2) . ? C4 C5 1.4894(18) . ? C5 C6 1.387(2) . ? C5 C10 1.4037(19) . ? C6 C7 1.387(2) . ? C6 H6 0.9500 . ? C7 C8 1.387(2) . ? C7 H7 0.9500 . ? C8 C9 1.384(2) . ? C8 H8 0.9500 . ? C9 C10 1.3944(18) . ? C9 H9 0.9500 . ? C10 C11 1.480(2) . ? C11 C12 1.4937(18) . ? C12 C13 1.380(2) . ? C13 C14 1.3954(18) . ? C13 H13 0.9500 . ? C15 C16 1.537(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 O4 S1 C17 105.96(7) . . ? O4 S1 C18 106.19(8) . . ? C17 S1 C18 97.55(8) . . ? C15 N1 C14 126.07(12) . . ? C15 N1 H1A 121.4(12) . . ? C14 N1 H1A 111.9(12) . . ? C2 C1 C14 119.90(12) . . ? C2 C1 H1 120.1 . . ? C14 C1 H1 120.1 . . ? C1 C2 C3 121.18(13) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C2 C3 C12 118.50(13) . . ? C2 C3 C4 120.07(12) . . ? C12 C3 C4 121.39(11) . . ? O1 C4 C3 121.53(12) . . ? O1 C4 C5 120.79(13) . . ? C3 C4 C5 117.68(12) . . ? C6 C5 C10 119.83(12) . . ? C6 C5 C4 119.20(12) . . ? C10 C5 C4 120.97(13) . . ? C7 C6 C5 120.27(13) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.00(14) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.31(13) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.14(13) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 119.45(13) . . ? C9 C10 C11 119.45(12) . . ? C5 C10 C11 121.10(12) . . ? O2 C11 C10 121.88(12) . . ? O2 C11 C12 120.40(13) . . ? C10 C11 C12 117.72(12) . . ? C13 C12 C3 120.74(12) . . ? C13 C12 C11 118.47(12) . . ? C3 C12 C11 120.78(13) . . ? C12 C13 C14 120.23(12) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C1 119.40(13) . . ? C13 C14 N1 116.67(12) . . ? C1 C14 N1 123.91(12) . . ? O3 C15 N1 128.01(15) . . ? O3 C15 C16 119.34(13) . . ? N1 C15 C16 112.63(12) . . ? F3 C16 F1 107.52(12) . . ? F3 C16 F2 107.23(13) . . ? F1 C16 F2 107.16(12) . . ? F3 C16 C15 110.67(12) . . ? F1 C16 C15 113.30(12) . . ? F2 C16 C15 110.69(12) . . ? S1 C17 H17A 109.5 . . ? S1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C14 C1 C2 C3 -1.0(2) . . . . ? C1 C2 C3 C12 -0.7(2) . . . . ? C1 C2 C3 C4 177.23(13) . . . . ? C2 C3 C4 O1 -3.3(2) . . . . ? C12 C3 C4 O1 174.58(13) . . . . ? C2 C3 C4 C5 176.18(12) . . . . ? C12 C3 C4 C5 -5.95(19) . . . . ? O1 C4 C5 C6 3.9(2) . . . . ? C3 C4 C5 C6 -175.61(12) . . . . ? O1 C4 C5 C10 -175.88(13) . . . . ? C3 C4 C5 C10 4.65(19) . . . . ? C10 C5 C6 C7 0.0(2) . . . . ? C4 C5 C6 C7 -179.72(13) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C6 C7 C8 C9 -0.2(2) . . . . ? C7 C8 C9 C10 0.4(2) . . . . ? C8 C9 C10 C5 -0.3(2) . . . . ? C8 C9 C10 C11 178.89(13) . . . . ? C6 C5 C10 C9 0.1(2) . . . . ? C4 C5 C10 C9 179.86(13) . . . . ? C6 C5 C10 C11 -179.08(13) . . . . ? C4 C5 C10 C11 0.7(2) . . . . ? C9 C10 C11 O2 -5.1(2) . . . . ? C5 C10 C11 O2 174.12(13) . . . . ? C9 C10 C11 C12 176.07(12) . . . . ? C5 C10 C11 C12 -4.7(2) . . . . ? C2 C3 C12 C13 1.1(2) . . . . ? C4 C3 C12 C13 -176.77(13) . . . . ? C2 C3 C12 C11 179.83(12) . . . . ? C4 C3 C12 C11 1.9(2) . . . . ? O2 C11 C12 C13 3.3(2) . . . . ? C10 C11 C12 C13 -177.84(12) . . . . ? O2 C11 C12 C3 -175.42(13) . . . . ? C10 C11 C12 C3 3.44(19) . . . . ? C3 C12 C13 C14 0.1(2) . . . . ? C11 C12 C13 C14 -178.61(12) . . . . ? C12 C13 C14 C1 -1.8(2) . . . . ? C12 C13 C14 N1 176.56(12) . . . . ? C2 C1 C14 C13 2.2(2) . . . . ? C2 C1 C14 N1 -176.02(13) . . . . ? C15 N1 C14 C13 176.31(13) . . . . ? C15 N1 C14 C1 -5.4(2) . . . . ? C14 N1 C15 O3 -8.2(2) . . . . ? C14 N1 C15 C16 170.49(13) . . . . ? O3 C15 C16 F3 -8.20(19) . . . . ? N1 C15 C16 F3 173.00(12) . . . . ? O3 C15 C16 F1 -129.05(14) . . . . ? N1 C15 C16 F1 52.15(17) . . . . ? O3 C15 C16 F2 110.54(15) . . . . ? N1 C15 C16 F2 -68.26(15) . . . . ? 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 H1A O4 0.832(17) 1.949(18) 2.7817(17) 180(2) 1_545 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.411 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.059