Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (c) The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1145 _publ_contact_author_name 'Todd B. Marder' _publ_contact_author_address ; Department of Chemistry University of Durham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email todd.marder@durham.ac.uk loop_ _publ_author_name 'Fasina, Tolulope M.' 'Collings, Jonathan C.' 'Lydon, Donocadh P.' 'Albesa-Jove, David' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' 'Nguyen, Paul' 'Bruce, Mitch' 'Scott, Andrew J.' 'Clegg, William' 'Watt, Stephen W.' 'Viney, Christopher' 'Marder, Todd B.' _journal_name_full 'Journal of Materials Chemistry' _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year 2004 _ccdc_journal_depnumber ? _publ_section_title ; Synthesis, optical properties, crystal structures and phase behaviour of selectively fluorinated 1,4-bis(4'-pyridylethynyl)benzenes, 4-(pyridylethynyl)benzenes and 9,10-bis(4'-pyridylethynyl)anthracene, and a Zn(NO~3~)~2~ coordination polymer ; #====================================================================== data_(1b) _database_code_depnum_ccdc_archive 'CCDC 235646' _audit_creation_method SHELXL _chemical_name_systematic ; 1,4-bis(4-pyridylethynyl)tetrafluorobenzene ; _chemical_name_common ? _chemical_formula_moiety 'C20 H8 F4 N2' _chemical_formula_sum 'C20 H8 F4 N2' _chemical_formula_weight 352.28 _chemical_melting_point '508 K (dec.)' _ccdc_comments 'K 500.8 S~B~ 545.7' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.7867(10) _cell_length_b 10.5564(12) _cell_length_c 13.1116(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.577(11) _cell_angle_gamma 90.00 _cell_volume 781.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 23.5 _cell_measurement_theta_max 32.3 _exptl_crystal_description 'hexagonal prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method . _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 1.060 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8934 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'T_max,min determined from \y-scans but not applied' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.4 _diffrn_reflns_number 1927 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.4 _diffrn_reflns_theta_max 75.0 _reflns_number_total 1542 _reflns_number_observed 1430 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'AFC (MSC, 1989)' _computing_cell_refinement 'AFC (MSC, 1989)' _computing_data_reduction 'TEXSAN version 5.1 (MSC, 1989)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.2958P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0053(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1541 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_obs 0.0357 _refine_ls_wR_factor_all 0.1075 _refine_ls_wR_factor_obs 0.1027 _refine_ls_goodness_of_fit_all 1.063 _refine_ls_goodness_of_fit_obs 1.078 _refine_ls_restrained_S_all 1.083 _refine_ls_restrained_S_obs 1.078 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.3131(2) 0.59750(12) 0.71580(10) 0.0372(3) Uani 1 d . . C2 C 0.4914(3) 0.61723(14) 0.66784(12) 0.0356(4) Uani 1 d . . H2 H 0.5295(33) 0.7058(22) 0.6612(14) 0.048(5) Uiso 1 d . . C3 C 0.6131(3) 0.52105(14) 0.63028(12) 0.0299(3) Uani 1 d . . H3 H 0.7339(36) 0.5416(19) 0.5978(16) 0.047(5) Uiso 1 d . . C4 C 0.5483(2) 0.39593(13) 0.64346(11) 0.0255(3) Uani 1 d . . C5 C 0.3631(3) 0.37339(13) 0.69362(12) 0.0295(3) Uani 1 d . . H5 H 0.3156(32) 0.2928(19) 0.7044(14) 0.042(5) Uiso 1 d . . C6 C 0.2531(3) 0.4766(2) 0.72768(12) 0.0347(4) Uani 1 d . . H6 H 0.1273(35) 0.4606(19) 0.7626(16) 0.046(5) Uiso 1 d . . C7 C 0.6668(2) 0.29264(13) 0.60519(11) 0.0284(3) Uani 1 d . . C8 C 0.7634(2) 0.20631(13) 0.57301(11) 0.0286(3) Uani 1 d . . C9 C 0.8806(2) 0.10318(13) 0.53579(10) 0.0258(3) Uani 1 d . . C10 C 1.0614(2) 0.12262(12) 0.48216(11) 0.0264(3) Uani 1 d . . C11 C 1.1766(2) 0.02263(13) 0.44763(11) 0.0260(3) Uani 1 d . . F10 F 1.1228(2) 0.24097(7) 0.46267(7) 0.0355(3) Uani 1 d . . F11 F 1.34788(14) 0.04691(8) 0.39584(7) 0.0343(3) Uani 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 N1 0.0450(7) 0.0303(7) 0.0365(7) -0.0046(5) 0.0095(6) 0.0110(5) C2 0.0494(9) 0.0215(7) 0.0358(8) 0.0000(5) 0.0090(7) 0.0029(6) C3 0.0349(7) 0.0250(7) 0.0315(7) 0.0017(5) 0.0108(6) -0.0009(5) C4 0.0282(7) 0.0223(6) 0.0262(7) -0.0004(5) 0.0061(5) 0.0028(5) C5 0.0316(7) 0.0262(7) 0.0325(7) -0.0008(5) 0.0108(5) -0.0022(5) C6 0.0324(7) 0.0384(8) 0.0358(8) -0.0027(6) 0.0130(6) 0.0030(6) C7 0.0301(7) 0.0245(7) 0.0313(7) 0.0004(5) 0.0083(5) 0.0015(5) C8 0.0291(7) 0.0257(7) 0.0315(7) -0.0014(5) 0.0079(5) 0.0023(5) C9 0.0260(6) 0.0235(7) 0.0278(7) -0.0022(5) 0.0056(5) 0.0036(5) C10 0.0284(7) 0.0207(6) 0.0300(7) 0.0002(5) 0.0063(5) -0.0010(5) C11 0.0238(6) 0.0279(7) 0.0281(7) -0.0002(5) 0.0094(5) 0.0006(5) F10 0.0405(5) 0.0205(4) 0.0484(6) 0.0017(3) 0.0161(4) -0.0026(3) F11 0.0325(4) 0.0336(5) 0.0418(5) 0.0009(4) 0.0193(4) 0.0000(3) _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 C2 1.336(2) . ? N1 C6 1.340(2) . ? C2 C3 1.386(2) . ? C2 H2 0.97(2) . ? C3 C4 1.394(2) . ? C3 H3 0.92(2) . ? C4 C5 1.395(2) . ? C4 C7 1.435(2) . ? C5 C6 1.384(2) . ? C5 H5 0.91(2) . ? C6 H6 0.96(2) . ? C7 C8 1.193(2) . ? C8 C9 1.424(2) . ? C9 C11 1.397(2) 3_756 ? C9 C10 1.397(2) . ? C10 F10 1.339(2) . ? C10 C11 1.376(2) . ? C11 F11 1.343(2) . ? C11 C9 1.397(2) 3_756 ? 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 C2 N1 C6 116.69(13) . . ? N1 C2 C3 123.87(14) . . ? N1 C2 H2 114.0(12) . . ? C3 C2 H2 122.1(12) . . ? C2 C3 C4 118.60(14) . . ? C2 C3 H3 119.2(13) . . ? C4 C3 H3 122.2(13) . . ? C3 C4 C5 118.38(13) . . ? C3 C4 C7 120.96(13) . . ? C5 C4 C7 120.66(13) . . ? C6 C5 C4 118.18(13) . . ? C6 C5 H5 120.5(12) . . ? C4 C5 H5 121.3(12) . . ? N1 C6 C5 124.28(14) . . ? N1 C6 H6 117.9(12) . . ? C5 C6 H6 117.8(12) . . ? C8 C7 C4 179.4(2) . . ? C7 C8 C9 179.33(15) . . ? C11 C9 C10 116.52(12) 3_756 . ? C11 C9 C8 121.81(13) 3_756 . ? C10 C9 C8 121.66(13) . . ? F10 C10 C11 119.03(13) . . ? F10 C10 C9 119.48(12) . . ? C11 C10 C9 121.48(13) . . ? F11 C11 C10 118.92(12) . . ? F11 C11 C9 119.07(12) . 3_756 ? C10 C11 C9 122.00(13) . 3_756 ? _refine_diff_density_max 0.251 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.040 #===========================================================END data_(1c) _database_code_depnum_ccdc_archive 'CCDC 235647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Bis(2,3,5,6-tetrafluoropyridylethynyl)benzene ; _chemical_name_common ? _chemical_melting_point '520 K (dec.)' _chemical_formula_moiety 'C20 H4 F8 N2' _chemical_formula_sum 'C20 H4 F8 N2' _chemical_formula_weight 424.25 _ccdc_comments 'K 587.1 I' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclcinic _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 8.920(2) _cell_length_b 5.060(1) _cell_length_c 18.101(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.93(3) _cell_angle_gamma 90.00 _cell_volume 816.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 582 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 25.8 _exptl_crystal_description needle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7925 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Bruker, 2001), R(int)=0.071 before correction' _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (30 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.85 cm. Pseudo-merohedral twinning by rotation around [1 0 2], component contributions 94 and 6%, reflections overlap only partially. ; _diffrn_ambient_temperature 110(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 'SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10667 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.0 _reflns_number_total 2373 _reflns_number_gt 1679 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. ; _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^)+(0.1090P)^2^+0.9864P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2373 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.2541 _refine_ls_wR_factor_gt 0.2317 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _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 F2 F -0.0905(2) 0.2752(4) 0.12876(12) 0.0433(5) Uani 1 1 d . . . F3 F 0.0334(2) 0.6933(4) 0.05887(9) 0.0362(5) Uani 1 1 d . . . F5 F 0.4083(2) 0.7066(4) 0.24904(9) 0.0359(5) Uani 1 1 d . . . F6 F 0.2654(2) 0.2917(4) 0.31081(10) 0.0433(5) Uani 1 1 d . . . N1 N 0.0893(3) 0.2866(5) 0.21905(14) 0.0309(5) Uani 1 1 d . . . C2 C 0.0340(3) 0.3876(5) 0.15724(16) 0.0290(6) Uani 1 1 d . . . C3 C 0.0969(3) 0.5984(5) 0.12140(14) 0.0258(5) Uani 1 1 d . . . C4 C 0.2275(3) 0.7126(5) 0.15028(13) 0.0224(5) Uani 1 1 d . . . C5 C 0.2847(3) 0.6056(5) 0.21620(14) 0.0261(5) Uani 1 1 d . . . C6 C 0.2110(3) 0.3951(6) 0.24768(15) 0.0298(6) Uani 1 1 d . . . C7 C 0.3000(3) 0.9236(5) 0.11371(13) 0.0239(5) Uani 1 1 d . . . C8 C 0.3604(3) 1.0963(5) 0.08047(13) 0.0241(5) Uani 1 1 d . . . C9 C 0.4313(3) 1.3013(5) 0.03969(13) 0.0225(5) Uani 1 1 d . . . C10 C 0.5695(3) 1.4024(5) 0.06467(13) 0.0259(5) Uani 1 1 d . . . H10 H 0.623(4) 1.336(8) 0.113(2) 0.037(9) Uiso 1 1 d . . . C11 C 0.3621(3) 1.3988(5) -0.02503(14) 0.0256(5) Uani 1 1 d . . . H11 H 0.267(4) 1.335(8) -0.039(2) 0.043(10) 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 F2 0.0344(10) 0.0409(11) 0.0546(12) -0.0011(9) 0.0022(8) -0.0141(8) F3 0.0366(9) 0.0444(10) 0.0269(8) 0.0051(7) -0.0075(7) -0.0052(8) F5 0.0361(9) 0.0423(10) 0.0286(8) 0.0026(7) -0.0090(7) -0.0038(7) F6 0.0551(12) 0.0441(11) 0.0307(9) 0.0183(8) 0.0038(8) 0.0092(9) N1 0.0351(12) 0.0238(11) 0.0345(12) 0.0037(9) 0.0140(10) 0.0018(9) C2 0.0278(13) 0.0251(12) 0.0345(13) -0.0027(10) 0.0080(10) -0.0036(10) C3 0.0281(12) 0.0246(12) 0.0248(12) 0.0007(9) 0.0030(9) 0.0002(10) C4 0.0259(11) 0.0211(11) 0.0204(11) -0.0005(8) 0.0042(9) 0.0006(9) C5 0.0312(13) 0.0240(12) 0.0234(11) -0.0003(9) 0.0031(9) 0.0019(10) C6 0.0382(14) 0.0269(13) 0.0247(12) 0.0061(10) 0.0080(10) 0.0064(11) C7 0.0283(12) 0.0234(12) 0.0200(10) -0.0007(9) 0.0026(9) 0.0001(9) C8 0.0272(12) 0.0236(12) 0.0215(11) -0.0008(9) 0.0023(9) 0.0013(9) C9 0.0256(12) 0.0230(11) 0.0191(10) -0.0009(9) 0.0033(9) 0.0006(9) C10 0.0286(12) 0.0287(13) 0.0201(11) 0.0039(9) -0.0019(9) -0.0012(10) C11 0.0260(12) 0.0290(13) 0.0215(11) 0.0020(9) -0.0021(9) -0.0051(10) _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 F2 C2 1.335(3) . ? F3 C3 1.338(3) . ? F5 C5 1.336(3) . ? F6 C6 1.333(3) . ? N1 C6 1.308(4) . ? N1 C2 1.311(4) . ? C2 C3 1.378(4) . ? C3 C4 1.387(4) . ? C4 C5 1.392(4) . ? C4 C7 1.423(3) . ? C5 C6 1.384(4) . ? C7 C8 1.199(4) . ? C8 C9 1.432(3) . ? C9 C11 1.396(3) . ? C9 C10 1.396(4) . ? C10 C11 1.388(4) 3_685 ? C10 H10 1.03(4) . ? C11 C10 1.388(4) 3_685 ? C11 H11 0.94(4) . ? 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 C6 N1 C2 117.3(2) . . ? N1 C2 F2 116.6(2) . . ? N1 C2 C3 123.8(3) . . ? F2 C2 C3 119.6(3) . . ? F3 C3 C2 120.6(2) . . ? F3 C3 C4 119.7(2) . . ? C2 C3 C4 119.7(2) . . ? C3 C4 C5 116.1(2) . . ? C3 C4 C7 121.8(2) . . ? C5 C4 C7 122.1(2) . . ? F5 C5 C6 120.5(2) . . ? F5 C5 C4 120.4(2) . . ? C6 C5 C4 119.1(2) . . ? N1 C6 F6 116.6(2) . . ? N1 C6 C5 124.0(2) . . ? F6 C6 C5 119.4(3) . . ? C8 C7 C4 177.6(3) . . ? C7 C8 C9 179.1(3) . . ? C11 C9 C10 120.2(2) . . ? C11 C9 C8 119.9(2) . . ? C10 C9 C8 119.9(2) . . ? C11 C10 C9 119.8(2) 3_685 . ? C11 C10 H10 118(2) 3_685 . ? C9 C10 H10 122(2) . . ? C10 C11 C9 120.0(2) 3_685 . ? C10 C11 H11 121(2) 3_685 . ? C9 C11 H11 119(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.473 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.093 #===========================================================END data_(2) _database_code_depnum_ccdc_archive 'CCDC 235648' _audit_creation_method SHELXL _chemical_name_systematic ; 9,10-bis(4-pyridyl-ethynyl)anthracene ; _chemical_name_common ? _chemical_melting_point 506 _chemical_formula_moiety 'C28 H16 N2' _chemical_formula_sum 'C28 H16 N2' _chemical_formula_weight 380.43 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.0445(13) _cell_length_b 23.945(3) _cell_length_c 7.2480(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.940(3) _cell_angle_gamma 90.00 _cell_volume 1902.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3510 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 28.41 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 5808 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2176 _reflns_number_observed 1779 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.7095P] 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 SHELXL _refine_ls_extinction_coef 0.0032(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2176 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 N1 N 0.5000 0.71826(6) 0.2500 0.0522(5) Uani 1 2 d S . . C1 C 0.59271(14) 0.68876(5) 0.20095(18) 0.0457(4) Uani 1 1 d . . . H1 H 0.6599 0.7088 0.1634 0.055 Uiso 1 1 calc R . . C2 C 0.59888(11) 0.63111(5) 0.20045(16) 0.0329(3) Uani 1 1 d . . . H2 H 0.6690 0.6125 0.1671 0.039 Uiso 1 1 calc R . . C3 C 0.5000 0.60101(6) 0.2500 0.0243(3) Uani 1 2 d S . . C4 C 0.5000 0.54129(6) 0.2500 0.0266(3) Uani 1 2 d S . . C5 C 0.5000 0.49121(6) 0.2500 0.0259(3) Uani 1 2 d S . . C6 C 0.5000 0.43156(6) 0.2500 0.0236(3) Uani 1 2 d S . . C7 C 0.60549(9) 0.40236(4) 0.21230(14) 0.0237(2) Uani 1 1 d . . . C8 C 0.71331(10) 0.43065(4) 0.17431(15) 0.0294(3) Uani 1 1 d . . . H8 H 0.7149 0.4703 0.1744 0.035 Uiso 1 1 calc R . . C9 C 0.81407(10) 0.40188(5) 0.13785(17) 0.0330(3) Uani 1 1 d . . . H9 H 0.8850 0.4216 0.1133 0.040 Uiso 1 1 calc R . . C10 C 0.81369(10) 0.34248(5) 0.13623(17) 0.0314(3) Uani 1 1 d . . . H10 H 0.8844 0.3227 0.1110 0.038 Uiso 1 1 calc R . . C11 C 0.71236(10) 0.31408(4) 0.17066(15) 0.0276(3) Uani 1 1 d . . . H11 H 0.7129 0.2744 0.1677 0.033 Uiso 1 1 calc R . . C12 C 0.60530(9) 0.34251(4) 0.21109(14) 0.0233(2) Uani 1 1 d . . . C13 C 0.5000 0.31343(5) 0.2500 0.0239(3) Uani 1 2 d S . . C14 C 0.5000 0.25363(6) 0.2500 0.0266(3) Uani 1 2 d S . . C15 C 0.5000 0.20364(6) 0.2500 0.0278(3) Uani 1 2 d S . . C16 C 0.5000 0.14371(6) 0.2500 0.0255(3) Uani 1 2 d S . . C17 C 0.42273(10) 0.11354(4) 0.11953(16) 0.0293(3) Uani 1 1 d . . . H17 H 0.3684 0.1323 0.0284 0.035 Uiso 1 1 calc R . . C18 C 0.42685(11) 0.05569(4) 0.12543(17) 0.0329(3) Uani 1 1 d . . . H18 H 0.3743 0.0357 0.0352 0.039 Uiso 1 1 calc R . . N2 N 0.5000 0.02625(5) 0.2500 0.0344(3) Uani 1 2 d S . . 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 0.0944(14) 0.0212(7) 0.0369(8) 0.000 -0.0087(9) 0.000 C1 0.0678(9) 0.0309(6) 0.0358(7) 0.0033(5) -0.0050(6) -0.0212(6) C2 0.0351(6) 0.0305(6) 0.0324(6) -0.0001(4) 0.0014(5) -0.0066(4) C3 0.0302(7) 0.0190(6) 0.0228(7) 0.000 -0.0010(6) 0.000 C4 0.0290(7) 0.0235(7) 0.0275(7) 0.000 0.0035(6) 0.000 C5 0.0294(7) 0.0206(7) 0.0277(7) 0.000 0.0041(6) 0.000 C6 0.0285(7) 0.0182(6) 0.0238(7) 0.000 0.0023(5) 0.000 C7 0.0275(5) 0.0195(5) 0.0237(5) 0.0000(4) 0.0021(4) -0.0007(4) C8 0.0309(6) 0.0228(5) 0.0346(6) 0.0007(4) 0.0047(4) -0.0034(4) C9 0.0281(5) 0.0315(6) 0.0401(7) 0.0014(5) 0.0076(5) -0.0039(4) C10 0.0277(5) 0.0311(6) 0.0361(6) -0.0012(4) 0.0063(5) 0.0045(4) C11 0.0314(6) 0.0219(5) 0.0295(5) 0.0004(4) 0.0038(4) 0.0040(4) C12 0.0271(5) 0.0193(5) 0.0232(5) 0.0003(3) 0.0018(4) 0.0009(3) C13 0.0303(7) 0.0176(6) 0.0236(7) 0.000 0.0028(6) 0.000 C14 0.0292(7) 0.0229(7) 0.0283(7) 0.000 0.0053(6) 0.000 C15 0.0313(7) 0.0218(7) 0.0315(8) 0.000 0.0085(6) 0.000 C16 0.0283(7) 0.0183(6) 0.0323(8) 0.000 0.0135(6) 0.000 C17 0.0304(6) 0.0236(5) 0.0349(6) 0.0003(4) 0.0078(5) 0.0011(4) C18 0.0362(6) 0.0226(5) 0.0406(6) -0.0040(4) 0.0078(5) -0.0037(4) N2 0.0410(8) 0.0196(6) 0.0442(8) 0.000 0.0122(6) 0.000 _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 C1 1.3273(17) . ? N1 C1 1.3273(17) 2_655 ? C1 H1 0.950 . ? C1 C2 1.3821(16) . ? C2 H2 0.950 . ? C2 C3 1.3913(13) . ? C3 C2 1.3913(13) 2_655 ? C3 C4 1.4299(19) . ? C4 C5 1.199(2) . ? C5 C6 1.4283(18) . ? C6 C7 1.4135(12) . ? C6 C7 1.4135(12) 2_655 ? C7 C8 1.4254(14) . ? C7 C12 1.4332(14) . ? C8 H8 0.950 . ? C8 C9 1.3616(16) . ? C9 H9 0.950 . ? C9 C10 1.4222(16) . ? C10 H10 0.950 . ? C10 C11 1.3582(15) . ? C11 H11 0.950 . ? C11 C12 1.4251(14) . ? C12 C13 1.4129(12) . ? C13 C12 1.4129(12) 2_655 ? C13 C14 1.4317(18) . ? C14 C15 1.197(2) . ? C15 C16 1.4349(19) . ? C16 C17 1.3962(13) . ? C16 C17 1.3962(13) 2_655 ? C17 H17 0.950 . ? C17 C18 1.3864(15) . ? C18 H18 0.950 . ? C18 N2 1.3374(14) . ? N2 C18 1.3374(14) 2_655 ? 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 C1 N1 C1 115.70(15) . 2_655 ? N1 C1 H1 117.6 . . ? N1 C1 C2 124.89(13) . . ? H1 C1 C2 117.6 . . ? C1 C2 H2 120.8 . . ? C1 C2 C3 118.44(12) . . ? H2 C2 C3 120.8 . . ? C2 C3 C2 117.60(14) . 2_655 ? C2 C3 C4 121.20(7) . . ? C2 C3 C4 121.20(7) 2_655 . ? C3 C4 C5 180.0 . . ? C4 C5 C6 180.0 . . ? C5 C6 C7 119.64(6) . . ? C5 C6 C7 119.64(6) . 2_655 ? C7 C6 C7 120.71(12) . 2_655 ? C6 C7 C8 121.99(10) . . ? C6 C7 C12 119.68(9) . . ? C8 C7 C12 118.34(9) . . ? C7 C8 H8 119.4 . . ? C7 C8 C9 121.23(10) . . ? H8 C8 C9 119.4 . . ? C8 C9 H9 119.8 . . ? C8 C9 C10 120.39(10) . . ? H9 C9 C10 119.8 . . ? C9 C10 H10 120.0 . . ? C9 C10 C11 120.06(10) . . ? H10 C10 C11 120.0 . . ? C10 C11 H11 119.3 . . ? C10 C11 C12 121.41(10) . . ? H11 C11 C12 119.3 . . ? C7 C12 C11 118.57(9) . . ? C7 C12 C13 119.49(9) . . ? C11 C12 C13 121.94(9) . . ? C12 C13 C12 120.94(12) . 2_655 ? C12 C13 C14 119.53(6) . . ? C12 C13 C14 119.53(6) 2_655 . ? C13 C14 C15 180.0 . . ? C14 C15 C16 180.0 . . ? C15 C16 C17 121.16(7) . . ? C15 C16 C17 121.16(7) . 2_655 ? C17 C16 C17 117.68(13) . 2_655 ? C16 C17 H17 120.6 . . ? C16 C17 C18 118.75(10) . . ? H17 C17 C18 120.6 . . ? C17 C18 H18 117.9 . . ? C17 C18 N2 124.22(11) . . ? H18 C18 N2 117.9 . . ? C18 N2 C18 116.38(13) . 2_655 ? 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 C1 N1 C1 C2 -0.91(8) 2_655 . . . ? N1 C1 C2 C3 1.78(16) . . . . ? C1 C2 C3 C2 -0.81(7) . . . 2_655 ? C1 C2 C3 C4 179.19(7) . . . . ? C5 C6 C7 C8 0.17(11) . . . . ? C5 C6 C7 C12 -179.60(6) . . . . ? C7 C6 C7 C8 -179.83(11) 2_655 . . . ? C7 C6 C7 C12 0.40(6) 2_655 . . . ? C6 C7 C8 C9 -179.85(9) . . . . ? C12 C7 C8 C9 -0.07(15) . . . . ? C7 C8 C9 C10 0.23(17) . . . . ? C8 C9 C10 C11 0.18(17) . . . . ? C9 C10 C11 C12 -0.75(17) . . . . ? C10 C11 C12 C7 0.89(15) . . . . ? C10 C11 C12 C13 -178.99(9) . . . . ? C6 C7 C12 C11 179.31(8) . . . . ? C6 C7 C12 C13 -0.80(13) . . . . ? C8 C7 C12 C11 -0.47(14) . . . . ? C8 C7 C12 C13 179.42(8) . . . . ? C7 C12 C13 C12 0.40(6) . . . 2_655 ? C7 C12 C13 C14 -179.60(6) . . . . ? C11 C12 C13 C12 -179.72(10) . . . 2_655 ? C11 C12 C13 C14 0.28(10) . . . . ? C15 C16 C17 C18 179.74(7) . . . . ? C17 C16 C17 C18 -0.26(7) 2_655 . . . ? C16 C17 C18 N2 0.56(16) . . . . ? C17 C18 N2 C18 -0.29(8) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.286 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.038 #===========================================================END data_(3a) _database_code_depnum_ccdc_archive 'CCDC 235649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-pyridylethynyl)pentafluorobenzene ; _chemical_name_common ? _chemical_melting_point 496--497 _chemical_formula_moiety 'C13 H4 F5 N' _chemical_formula_sum 'C13 H4 F5 N' _chemical_formula_weight 269.17 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' F F 0.0171 0.0103 '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' _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 5.834(2) _cell_length_b 8.965(3) _cell_length_c 11.009(4) _cell_angle_alpha 71.17(1) _cell_angle_beta 82.05(1) _cell_angle_gamma 80.99(1) _cell_volume 535.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 731 _cell_measurement_theta_min 4.831 _cell_measurement_theta_max 60.521 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.85 cm. ; _diffrn_ambient_temperature 120(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 'SMART 6000 CCD area deterctor' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 7323 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 30.50 _reflns_number_total 3206 _reflns_number_gt 1621 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. ; _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^)+(0.0634P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3206 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1185 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.923 _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 0.3251(3) 0.1310(2) -0.41862(17) 0.0284(4) Uani 1 1 d . . . C2 C 0.1716(4) 0.2207(2) -0.3606(2) 0.0290(5) Uani 1 1 d . . . H2 H 0.037(4) 0.263(3) -0.404(2) 0.039(7) Uiso 1 1 d . . . C3 C 0.2075(4) 0.2533(2) -0.2516(2) 0.0274(5) Uani 1 1 d . . . H3 H 0.104(4) 0.318(2) -0.214(2) 0.031(6) Uiso 1 1 d . . . C4 C 0.4162(3) 0.1909(2) -0.19598(18) 0.0215(4) Uani 1 1 d . . . C5 C 0.5773(3) 0.0973(2) -0.2550(2) 0.0246(4) Uani 1 1 d . . . H5 H 0.723(4) 0.047(3) -0.213(2) 0.041(7) Uiso 1 1 d . . . C6 C 0.5245(4) 0.0711(2) -0.3637(2) 0.0257(4) Uani 1 1 d . . . H6 H 0.623(4) 0.011(3) -0.408(2) 0.031(6) Uiso 1 1 d . . . C7 C 0.4634(3) 0.2240(2) -0.0841(2) 0.0257(4) Uani 1 1 d . . . C8 C 0.5049(3) 0.2543(2) 0.00839(19) 0.0238(4) Uani 1 1 d . . . C9 C 0.5497(3) 0.2896(2) 0.11856(18) 0.0216(4) Uani 1 1 d . . . C14 C 0.7562(3) 0.2304(2) 0.17617(19) 0.0230(4) Uani 1 1 d . . . F14 F 0.9187(2) 0.13966(14) 0.12459(12) 0.0357(3) Uani 1 1 d . . . C13 C 0.7964(3) 0.2609(2) 0.2853(2) 0.0250(4) Uani 1 1 d . . . F13 F 0.9962(2) 0.19980(15) 0.33971(12) 0.0352(3) Uani 1 1 d . . . C12 C 0.6329(3) 0.3534(2) 0.34031(18) 0.0235(4) Uani 1 1 d . . . F12 F 0.6739(2) 0.38579(14) 0.44459(12) 0.0342(3) Uani 1 1 d . . . C11 C 0.4253(3) 0.4143(2) 0.28582(19) 0.0240(4) Uani 1 1 d . . . F11 F 0.2643(2) 0.50374(14) 0.33965(12) 0.0342(3) Uani 1 1 d . . . C10 C 0.3869(3) 0.3828(2) 0.17702(19) 0.0226(4) Uani 1 1 d . . . F10 F 0.1855(2) 0.44475(13) 0.12552(11) 0.0289(3) 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 N1 0.0300(10) 0.0292(9) 0.0271(9) -0.0091(7) -0.0072(8) -0.0017(7) C2 0.0251(10) 0.0321(11) 0.0291(11) -0.0075(9) -0.0100(9) 0.0016(9) C3 0.0251(10) 0.0293(11) 0.0274(11) -0.0103(9) -0.0049(9) 0.0035(8) C4 0.0253(10) 0.0183(9) 0.0202(9) -0.0037(7) -0.0044(8) -0.0036(7) C5 0.0237(11) 0.0225(10) 0.0251(10) -0.0035(8) -0.0041(9) -0.0016(8) C6 0.0275(11) 0.0236(10) 0.0253(10) -0.0082(8) -0.0027(9) 0.0010(8) C7 0.0259(11) 0.0206(10) 0.0277(10) -0.0040(8) -0.0044(9) -0.0004(8) C8 0.0257(10) 0.0192(9) 0.0244(10) -0.0036(7) -0.0036(8) -0.0018(8) C9 0.0229(10) 0.0187(9) 0.0220(10) -0.0029(7) -0.0043(8) -0.0040(7) C14 0.0220(10) 0.0208(10) 0.0247(10) -0.0057(8) -0.0034(8) -0.0002(8) F14 0.0272(7) 0.0378(7) 0.0406(8) -0.0150(6) -0.0058(6) 0.0091(5) C13 0.0191(9) 0.0246(10) 0.0279(11) -0.0005(8) -0.0090(8) -0.0030(7) F13 0.0236(6) 0.0405(7) 0.0389(7) -0.0057(6) -0.0162(6) 0.0018(5) C12 0.0285(10) 0.0251(10) 0.0188(9) -0.0054(8) -0.0058(8) -0.0080(8) F12 0.0411(8) 0.0386(7) 0.0269(6) -0.0105(5) -0.0125(6) -0.0073(6) C11 0.0219(10) 0.0240(10) 0.0244(10) -0.0064(8) -0.0017(8) -0.0004(8) F11 0.0325(7) 0.0383(7) 0.0330(7) -0.0176(6) -0.0032(6) 0.0067(5) C10 0.0182(9) 0.0225(10) 0.0253(10) -0.0026(8) -0.0078(8) -0.0023(7) F10 0.0207(6) 0.0339(7) 0.0307(7) -0.0077(5) -0.0103(5) 0.0033(5) _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 C6 1.341(3) . ? N1 C2 1.343(3) . ? C2 C3 1.373(3) . ? C3 C4 1.394(3) . ? C4 C5 1.395(3) . ? C4 C7 1.427(3) . ? C5 C6 1.374(3) . ? C7 C8 1.199(3) . ? C8 C9 1.414(3) . ? C9 C14 1.389(3) . ? C9 C10 1.394(3) . ? C14 F14 1.338(2) . ? C14 C13 1.372(3) . ? C13 F13 1.342(2) . ? C13 C12 1.372(3) . ? C12 F12 1.331(2) . ? C12 C11 1.381(3) . ? C11 F11 1.339(2) . ? C11 C10 1.370(3) . ? C10 F10 1.337(2) . ? 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 C6 N1 C2 116.07(18) . . ? N1 C2 C3 124.37(19) . . ? C2 C3 C4 118.93(19) . . ? C3 C4 C5 117.39(18) . . ? C3 C4 C7 120.99(18) . . ? C5 C4 C7 121.62(17) . . ? C6 C5 C4 119.26(18) . . ? N1 C6 C5 123.99(19) . . ? C8 C7 C4 178.8(2) . . ? C7 C8 C9 179.0(2) . . ? C14 C9 C10 116.31(18) . . ? C14 C9 C8 121.83(18) . . ? C10 C9 C8 121.85(17) . . ? F14 C14 C13 119.27(17) . . ? F14 C14 C9 119.00(18) . . ? C13 C14 C9 121.73(19) . . ? F13 C13 C12 119.18(18) . . ? F13 C13 C14 120.25(18) . . ? C12 C13 C14 120.57(18) . . ? F12 C12 C13 120.60(18) . . ? F12 C12 C11 120.03(18) . . ? C13 C12 C11 119.37(18) . . ? F11 C11 C10 120.79(18) . . ? F11 C11 C12 119.66(18) . . ? C10 C11 C12 119.55(19) . . ? F10 C10 C11 118.27(18) . . ? F10 C10 C9 119.25(17) . . ? C11 C10 C9 122.48(18) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 30.54 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.358 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.062 #===========================================================END data_(3b) _database_code_depnum_ccdc_archive 'CCDC 235650' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(phenylethynyl)-2,3,5,6-tetrafluoropyridine ; _chemical_name_common ? _chemical_melting_point 378--378 _chemical_formula_moiety 'C13 H5 F4 N' _chemical_formula_sum 'C13 H5 F4 N' _chemical_formula_weight 251.18 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' F F 0.0171 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 5.0314(15) _cell_length_b 8.831(3) _cell_length_c 23.579(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1047.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 911 _cell_measurement_theta_min 12.10 _cell_measurement_theta_max 24.15 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered nearly full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (15 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.42 cm. With Friedel pairs not merged, 2778 unique reflections. ; _diffrn_ambient_temperature 120(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 'smart 1k CCD area detector' _diffrn_measurement_method '\W scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 11716 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 29.03 _reflns_number_total 1648 _reflns_number_gt 1548 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.686 _computing_data_collection 'SMART version 5.060 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.060 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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. ; _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^)+(0.0349P)^2^+0.3031P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'undeterminable, Friedel pair merged, all \Df" set to 0' _refine_ls_number_reflns 1648 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 1.0467(3) 0.65290(19) 0.02341(7) 0.0255(3) Uani 1 1 d . . . F2 F 1.0855(3) 0.82397(14) 0.09380(6) 0.0395(3) Uani 1 1 d . . . F3 F 0.6767(3) 0.69974(14) 0.15141(5) 0.0340(3) Uani 1 1 d . . . F5 F 0.5974(3) 0.34421(14) 0.00255(5) 0.0347(3) Uani 1 1 d . . . F6 F 1.0151(3) 0.48358(15) -0.04758(5) 0.0374(3) Uani 1 1 d . . . C2 C 0.9600(4) 0.7038(2) 0.07186(8) 0.0252(4) Uani 1 1 d . . . C3 C 0.7499(4) 0.6411(2) 0.10156(7) 0.0228(4) Uani 1 1 d . . . C4 C 0.6198(3) 0.51535(19) 0.07958(7) 0.0200(3) Uani 1 1 d . . . C5 C 0.7125(4) 0.4628(2) 0.02744(7) 0.0223(4) Uani 1 1 d . . . C6 C 0.9252(4) 0.5353(2) 0.00207(7) 0.0246(4) Uani 1 1 d . . . C7 C 0.4081(4) 0.4425(2) 0.10911(8) 0.0231(4) Uani 1 1 d . . . C8 C 0.2352(4) 0.3790(2) 0.13458(7) 0.0220(3) Uani 1 1 d . . . C9 C 0.0278(3) 0.30298(19) 0.16542(7) 0.0193(3) Uani 1 1 d . . . C10 C -0.0533(4) 0.3581(2) 0.21805(8) 0.0251(4) Uani 1 1 d . . . H10 H 0.024(6) 0.451(3) 0.2347(11) 0.049(8) Uiso 1 1 d . . . C11 C -0.2530(4) 0.2849(2) 0.24786(8) 0.0258(4) Uani 1 1 d . . . H11 H -0.306(5) 0.321(3) 0.2818(11) 0.037(7) Uiso 1 1 d . . . C12 C -0.3747(4) 0.1576(2) 0.22533(8) 0.0238(4) Uani 1 1 d . . . H12 H -0.506(6) 0.106(3) 0.2449(11) 0.032(6) Uiso 1 1 d . . . C13 C -0.2942(4) 0.1026(2) 0.17295(8) 0.0256(4) Uani 1 1 d . . . H13 H -0.380(5) 0.010(3) 0.1568(11) 0.041(7) Uiso 1 1 d . . . C14 C -0.0931(4) 0.1740(2) 0.14301(7) 0.0240(4) Uani 1 1 d . . . H14 H -0.048(5) 0.137(3) 0.1077(10) 0.032(6) 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 N1 0.0183(7) 0.0316(8) 0.0266(7) 0.0117(6) 0.0046(6) 0.0036(7) F2 0.0391(7) 0.0343(6) 0.0450(7) 0.0011(5) 0.0041(6) -0.0141(6) F3 0.0399(7) 0.0346(6) 0.0276(6) -0.0044(5) 0.0116(5) -0.0022(6) F5 0.0369(7) 0.0359(6) 0.0312(6) -0.0055(5) -0.0017(6) -0.0048(6) F6 0.0382(7) 0.0499(7) 0.0240(6) 0.0033(5) 0.0122(5) 0.0101(6) C2 0.0208(8) 0.0248(8) 0.0300(9) 0.0079(7) 0.0009(7) -0.0011(7) C3 0.0229(8) 0.0250(8) 0.0205(7) 0.0037(7) 0.0049(7) 0.0032(7) C4 0.0151(7) 0.0245(8) 0.0204(7) 0.0081(7) 0.0005(6) 0.0037(7) C5 0.0203(8) 0.0255(8) 0.0212(8) 0.0038(7) -0.0015(7) 0.0027(7) C6 0.0213(8) 0.0331(9) 0.0194(7) 0.0066(7) 0.0045(7) 0.0083(8) C7 0.0185(8) 0.0263(8) 0.0245(8) 0.0052(7) 0.0008(7) 0.0032(7) C8 0.0182(8) 0.0249(8) 0.0228(8) 0.0043(7) -0.0007(7) 0.0023(7) C9 0.0155(7) 0.0220(7) 0.0206(7) 0.0054(6) 0.0003(6) 0.0011(7) C10 0.0240(8) 0.0258(8) 0.0256(8) -0.0023(7) 0.0026(7) -0.0051(7) C11 0.0277(10) 0.0276(9) 0.0221(8) -0.0021(7) 0.0081(8) -0.0010(8) C12 0.0211(8) 0.0247(8) 0.0256(8) 0.0073(7) 0.0028(7) -0.0023(7) C13 0.0287(9) 0.0224(8) 0.0258(9) 0.0011(7) -0.0007(8) -0.0060(8) C14 0.0286(9) 0.0254(8) 0.0181(8) 0.0012(7) 0.0027(7) -0.0007(8) _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 C2 1.303(2) . ? N1 C6 1.306(3) . ? F2 C2 1.339(2) . ? F3 C3 1.336(2) . ? F5 C5 1.333(2) . ? F6 C6 1.336(2) . ? C2 C3 1.383(2) . ? C3 C4 1.390(3) . ? C4 C5 1.395(2) . ? C4 C7 1.426(2) . ? C5 C6 1.383(3) . ? C7 C8 1.196(3) . ? C8 C9 1.438(2) . ? C9 C10 1.394(2) . ? C9 C14 1.395(3) . ? C10 C11 1.386(3) . ? C10 H10 0.99(3) . ? C11 C12 1.387(3) . ? C11 H11 0.90(3) . ? C12 C13 1.387(3) . ? C12 H12 0.92(3) . ? C13 C14 1.385(3) . ? C13 H13 1.00(3) . ? C14 H14 0.92(2) . ? 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 C2 N1 C6 117.07(16) . . ? N1 C2 F2 117.00(17) . . ? N1 C2 C3 124.20(18) . . ? F2 C2 C3 118.80(18) . . ? F3 C3 C2 120.07(17) . . ? F3 C3 C4 120.52(16) . . ? C2 C3 C4 119.39(16) . . ? C3 C4 C5 115.92(16) . . ? C3 C4 C7 122.04(16) . . ? C5 C4 C7 122.03(17) . . ? F5 C5 C6 120.63(17) . . ? F5 C5 C4 120.28(16) . . ? C6 C5 C4 119.10(17) . . ? N1 C6 F6 116.79(17) . . ? N1 C6 C5 124.32(17) . . ? F6 C6 C5 118.90(18) . . ? C8 C7 C4 178.30(19) . . ? C7 C8 C9 179.8(2) . . ? C10 C9 C14 119.63(16) . . ? C10 C9 C8 119.96(16) . . ? C14 C9 C8 120.41(16) . . ? C11 C10 C9 120.08(17) . . ? C11 C10 H10 118.0(16) . . ? C9 C10 H10 121.8(16) . . ? C10 C11 C12 120.25(18) . . ? C10 C11 H11 120.1(17) . . ? C12 C11 H11 119.7(17) . . ? C11 C12 C13 119.72(17) . . ? C11 C12 H12 121.6(16) . . ? C13 C12 H12 118.7(16) . . ? C14 C13 C12 120.51(17) . . ? C14 C13 H13 119.5(15) . . ? C12 C13 H13 120.0(15) . . ? C13 C14 C9 119.80(17) . . ? C13 C14 H14 118.8(16) . . ? C9 C14 H14 121.3(15) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.249 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.046 #===========================================================END data_(4) _database_code_depnum_ccdc_archive 'CCDC 235651' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-bis(4-pyridylethynyl)tetrafluorobenzene complex with zinc nitrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H8 F4 N4 O6 Zn' _chemical_formula_sum 'C20 H8 F4 N4 O6 Zn' _chemical_formula_weight 541.67 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' Zn Zn 0.2839 1.4301 '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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.7318(13) _cell_length_b 5.2736(5) _cell_length_c 16.5263(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.428(5) _cell_angle_gamma 90.00 _cell_volume 1016.03(18) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 978 _cell_measurement_theta_min 6.990 _cell_measurement_theta_max 60.652 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 1.294 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ;The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.96 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '60W microfocus Bede Microsource with glass polycapillary optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ProteumM APEX CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 7359 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 29.00 _reflns_number_total 2702 _reflns_number_gt 2484 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.28A (Bruker, 2002)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. The highest residual peaks of electron density correspond to the \p-electron area of C\\tp C bond. ; _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^)+(0.0410P)^2^+0.6393P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2702 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Zn1 Zn 0.5000 1.31342(4) 0.2500 0.01529(8) Uani 1 2 d S . . O1 O 0.52569(11) 1.5854(2) 0.33423(7) 0.0240(3) Uani 1 1 d . . . O2 O 0.61886(13) 1.6568(3) 0.45304(9) 0.0361(3) Uani 1 1 d . . . O3 O 0.64383(12) 1.3032(2) 0.39008(8) 0.0289(3) Uani 1 1 d . . . N2 N 0.59868(12) 1.5150(3) 0.39470(8) 0.0200(3) Uani 1 1 d . . . N1 N 0.61805(11) 1.0907(2) 0.20410(8) 0.0160(2) Uani 1 1 d . . . C2 C 0.68718(14) 0.9352(3) 0.25215(9) 0.0194(3) Uani 1 1 d . . . H2 H 0.6883 0.9492 0.3095 0.023 Uiso 1 1 calc R . . C3 C 0.75624(15) 0.7567(3) 0.22115(10) 0.0211(3) Uani 1 1 d . . . H3 H 0.8041 0.6501 0.2567 0.025 Uiso 1 1 calc R . . C6 C 0.61803(14) 1.0710(3) 0.12286(9) 0.0194(3) Uani 1 1 d . . . H6 H 0.5701 1.1814 0.0888 0.023 Uiso 1 1 calc R . . C5 C 0.68471(14) 0.8971(3) 0.08698(9) 0.0199(3) Uani 1 1 d . . . H5 H 0.6826 0.8887 0.0294 0.024 Uiso 1 1 calc R . . C4 C 0.75514(13) 0.7341(3) 0.13670(10) 0.0179(3) Uani 1 1 d . . . C7 C 0.82471(14) 0.5464(3) 0.10278(9) 0.0207(3) Uani 1 1 d . . . C8 C 0.87908(14) 0.3873(3) 0.07418(10) 0.0208(3) Uani 1 1 d . . . C9 C 0.94042(13) 0.1940(3) 0.03734(10) 0.0187(3) Uani 1 1 d . . . C11 C 1.01319(14) 0.0260(3) 0.08303(9) 0.0222(3) Uani 1 1 d . . . F11 F 1.02598(11) 0.0458(3) 0.16437(6) 0.0370(3) Uani 1 1 d . . . C10 C 0.92931(14) 0.1629(3) -0.04713(10) 0.0214(3) Uani 1 1 d . . . F10 F 0.86319(11) 0.3237(2) -0.09386(7) 0.0350(3) 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 Zn1 0.01855(13) 0.01331(12) 0.01506(13) 0.000 0.00645(9) 0.000 O1 0.0308(6) 0.0217(6) 0.0189(5) -0.0017(5) -0.0001(5) 0.0007(5) O2 0.0427(8) 0.0388(8) 0.0254(6) -0.0183(6) -0.0022(6) 0.0013(6) O3 0.0350(7) 0.0254(6) 0.0262(6) -0.0028(5) 0.0028(5) 0.0054(5) N2 0.0228(7) 0.0213(6) 0.0165(6) -0.0027(5) 0.0043(5) -0.0035(5) N1 0.0185(6) 0.0153(6) 0.0151(6) -0.0011(5) 0.0050(5) 0.0005(5) C2 0.0235(7) 0.0206(7) 0.0143(7) -0.0008(6) 0.0030(6) 0.0017(6) C3 0.0244(8) 0.0219(7) 0.0166(7) -0.0012(6) 0.0003(6) 0.0059(6) C6 0.0228(7) 0.0201(7) 0.0157(7) 0.0024(6) 0.0045(6) 0.0027(6) C5 0.0244(8) 0.0220(7) 0.0142(7) -0.0009(6) 0.0059(6) 0.0024(6) C4 0.0178(7) 0.0181(7) 0.0184(7) -0.0024(6) 0.0042(6) 0.0004(5) C7 0.0239(8) 0.0229(7) 0.0155(7) -0.0024(6) 0.0032(6) -0.0018(6) C8 0.0193(7) 0.0234(7) 0.0197(7) -0.0010(6) 0.0026(6) 0.0008(6) C9 0.0181(7) 0.0212(7) 0.0173(7) -0.0032(6) 0.0042(6) 0.0020(6) C11 0.0243(8) 0.0285(8) 0.0138(7) -0.0034(6) 0.0028(6) 0.0055(7) F11 0.0484(7) 0.0489(7) 0.0131(5) -0.0055(5) 0.0009(4) 0.0236(6) C10 0.0224(8) 0.0249(8) 0.0169(7) -0.0008(6) 0.0013(6) 0.0076(6) F10 0.0430(7) 0.0408(7) 0.0205(5) 0.0004(4) 0.0002(5) 0.0249(5) _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 Zn1 O1 1.9978(12) . ? Zn1 O1 1.9978(12) 2_655 ? Zn1 N1 2.0270(13) 2_655 ? Zn1 N1 2.0270(13) . ? O1 N2 1.2953(18) . ? O2 N2 1.2221(18) . ? O3 N2 1.2422(19) . ? N1 C6 1.3466(19) . ? N1 C2 1.348(2) . ? C2 C3 1.378(2) . ? C3 C4 1.399(2) . ? C6 C5 1.381(2) . ? C5 C4 1.394(2) . ? C4 C7 1.436(2) . ? C7 C8 1.184(2) . ? C8 C9 1.423(2) . ? C9 C11 1.393(2) . ? C9 C10 1.397(2) . ? C11 F11 1.3398(18) . ? C11 C10 1.375(2) 3_755 ? C10 F10 1.3354(19) . ? C10 C11 1.375(2) 3_755 ? 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 Zn1 O1 88.25(7) . 2_655 ? O1 Zn1 N1 102.20(5) . 2_655 ? O1 Zn1 N1 128.37(5) 2_655 2_655 ? O1 Zn1 N1 128.37(5) . . ? O1 Zn1 N1 102.20(5) 2_655 . ? N1 Zn1 N1 109.16(7) 2_655 . ? N2 O1 Zn1 111.53(10) . . ? O2 N2 O3 123.52(15) . . ? O2 N2 O1 119.10(15) . . ? O3 N2 O1 117.38(13) . . ? C6 N1 C2 118.26(13) . . ? C6 N1 Zn1 119.60(11) . . ? C2 N1 Zn1 121.56(10) . . ? N1 C2 C3 122.46(14) . . ? C2 C3 C4 119.26(15) . . ? N1 C6 C5 122.84(15) . . ? C6 C5 C4 118.87(14) . . ? C5 C4 C3 118.30(14) . . ? C5 C4 C7 121.33(14) . . ? C3 C4 C7 120.37(15) . . ? C8 C7 C4 177.95(18) . . ? C7 C8 C9 177.61(18) . . ? C11 C9 C10 116.75(14) . . ? C11 C9 C8 122.16(14) . . ? C10 C9 C8 121.08(15) . . ? F11 C11 C10 118.97(15) . 3_755 ? F11 C11 C9 119.17(14) . . ? C10 C11 C9 121.85(15) 3_755 . ? F10 C10 C11 119.48(15) . 3_755 ? F10 C10 C9 119.12(14) . . ? C11 C10 C9 121.39(15) 3_755 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.734 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.071 #==================================================END