# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Guru Row, Tayur' _publ_contact_author_email ssctng@sscu.iisc.ernet.in _publ_section_title ; Crystal structures of fluorinated aryl biscarbonates and a biscarbamate: A counterpoise between weak intermolecular interactions and molecular symmetry ; loop_ _publ_author_name A.Dikundwar C.Venkateswarlu R.Piltz S.C.N.CHANDRASEKARAN ; T.Guru Row ; #=============================================================================== data_vencdm_m _database_code_depnum_ccdc_archive 'CCDC 784067' #TrackingRef '1_acta.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'But-2-yne-1,4-diyl bis(2,3,4,5,6-pentafluorophenylcarbonate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H4 F10 O6' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C18 H4 F10 O6' _chemical_formula_iupac ? _chemical_formula_weight 506.21 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'A 2 -2ac' _symmetry_space_group_name_H-M 'A b a 2' _symmetry_Int_Tables_number 41 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,z 3 1/2-x,y,1/2+z 4 1/2+x,-y,1/2+z 5 x,1/2+y,1/2+z 6 -x,1/2-y,1/2+z 7 1/2-x,1/2+y,z 8 1/2+x,1/2-y,z _cell_length_a 16.3233(5) _cell_length_b 9.9385(4) _cell_length_c 10.9883(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1782.62(11) _cell_formula_units_Z 4 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used 66736 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 53.73 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.886 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.206 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.9522 _exptl_absorpt_correction_T_max 0.9541 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 90(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 66736 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 53.73 _diffrn_reflns_theta_full 53.73 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 10628 # number of observed reflections (> n sig(I)) _reflns_number_gt 8863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0602P)^2^+0.1647P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(2) _refine_ls_number_reflns 10628 _refine_ls_number_parameters 162 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.672 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.077 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 C9 C 0.18647(3) 0.18249(5) 0.04543(5) 0.01489(7) Uani 1 1 d . . . O3 O 0.16798(2) 0.29949(5) -0.14266(4) 0.01723(6) Uani 1 1 d . . . C5 C 0.13378(3) 0.40783(5) 0.04745(5) 0.01670(7) Uani 1 1 d . . . C4 C 0.16096(3) 0.29628(5) -0.01764(5) 0.01421(6) Uani 1 1 d . . . C8 C 0.18616(3) 0.18049(5) 0.17174(5) 0.01567(7) Uani 1 1 d . . . F5 F 0.21111(3) 0.07383(5) -0.01559(4) 0.02297(8) Uani 1 1 d . . . O1 O 0.11729(2) 0.30352(4) -0.32307(4) 0.01597(6) Uani 1 1 d . . . C7 C 0.15935(3) 0.29213(6) 0.23590(5) 0.01620(7) Uani 1 1 d . . . F4 F 0.21112(3) 0.07120(5) 0.23137(5) 0.02431(8) Uani 1 1 d . . . C3 C 0.09658(3) 0.29659(5) -0.20650(5) 0.01444(6) Uani 1 1 d . . . F3 F 0.15914(3) 0.29066(5) 0.35720(4) 0.02346(8) Uani 1 1 d . . . F1 F 0.10814(3) 0.51740(4) -0.01160(5) 0.02557(8) Uani 1 1 d . . . F2 F 0.10459(4) 0.51152(5) 0.23592(6) 0.02824(9) Uani 1 1 d . . . C1 C 0.01340(3) 0.44363(5) -0.41018(5) 0.01623(7) Uani 1 1 d . . . C2 C 0.04807(3) 0.30865(5) -0.40622(5) 0.01640(7) Uani 1 1 d . . . C6 C 0.13241(3) 0.40560(6) 0.17379(6) 0.01756(7) Uani 1 1 d . . . O2 O 0.02936(3) 0.28808(5) -0.16314(4) 0.01890(7) Uani 1 1 d . . . H2A H 0.0070(9) 0.2413(16) -0.3780(17) 0.025(3) Uiso 1 1 d . . . H2B H 0.0708(9) 0.2800(13) -0.4851(14) 0.019(3) 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 C9 0.01635(16) 0.01496(16) 0.01336(15) 0.00001(12) -0.00061(12) 0.00210(12) O3 0.01344(12) 0.02546(17) 0.01280(12) 0.00317(12) 0.00047(9) 0.00181(11) C5 0.01839(18) 0.01351(15) 0.01821(18) 0.00097(13) 0.00084(14) 0.00023(12) C4 0.01414(15) 0.01559(15) 0.01290(15) 0.00139(12) 0.00049(11) 0.00048(12) C8 0.01663(15) 0.01688(17) 0.01351(15) 0.00190(12) -0.00138(13) 0.00023(12) F5 0.02969(19) 0.01959(14) 0.01963(16) -0.00377(12) -0.00102(13) 0.00900(13) O1 0.01444(12) 0.02113(15) 0.01234(11) 0.00119(10) 0.00146(9) 0.00171(10) C7 0.01455(17) 0.0213(2) 0.01280(16) -0.00171(13) 0.00050(11) -0.00243(13) F4 0.0303(2) 0.02318(17) 0.01946(17) 0.00705(13) -0.00343(14) 0.00488(15) C3 0.01382(14) 0.01627(15) 0.01323(14) 0.00099(12) 0.00158(12) 0.00122(11) F3 0.01977(14) 0.0383(2) 0.01232(12) -0.00262(13) 0.00098(10) -0.00344(13) F1 0.0322(2) 0.01532(13) 0.0292(2) 0.00506(13) 0.00030(16) 0.00478(13) F2 0.0339(2) 0.02208(17) 0.0287(2) -0.01092(16) 0.00334(17) 0.00342(16) C1 0.01550(14) 0.01899(16) 0.01420(15) 0.00009(12) 0.00043(11) 0.00101(12) C2 0.01666(15) 0.01840(16) 0.01414(16) -0.00200(12) -0.00006(12) 0.00086(12) C6 0.01865(17) 0.01597(17) 0.01808(18) -0.00412(14) 0.00161(15) -0.00073(13) O2 0.01391(12) 0.02726(18) 0.01553(14) 0.00073(12) 0.00301(10) -0.00054(11) _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 C9 F5 1.3333(7) . ? C9 C8 1.3881(7) . ? C9 C4 1.3902(7) . ? O3 C3 1.3607(6) . ? O3 C4 1.3789(7) . ? C5 F1 1.3349(7) . ? C5 C6 1.3886(8) . ? C5 C4 1.3920(7) . ? C8 F4 1.3323(7) . ? C8 C7 1.3855(8) . ? O1 C3 1.3266(6) . ? O1 C2 1.4539(7) . ? C7 F3 1.3329(7) . ? C7 C6 1.3895(9) . ? C3 O2 1.1991(6) . ? F2 C6 1.3343(7) . ? C1 C1 1.2029(11) 2_565 ? C1 C2 1.4567(7) . ? C2 H2A 0.997(16) . ? C2 H2B 0.985(16) . ? 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 F5 C9 C8 119.49(5) . . ? F5 C9 C4 119.91(5) . . ? C8 C9 C4 120.60(5) . . ? C3 O3 C4 116.22(4) . . ? F1 C5 C6 119.60(6) . . ? F1 C5 C4 119.99(5) . . ? C6 C5 C4 120.40(5) . . ? O3 C4 C9 119.38(5) . . ? O3 C4 C5 121.33(5) . . ? C9 C4 C5 119.16(5) . . ? F4 C8 C7 119.95(5) . . ? F4 C8 C9 120.16(5) . . ? C7 C8 C9 119.90(5) . . ? C3 O1 C2 114.24(4) . . ? F3 C7 C8 120.05(5) . . ? F3 C7 C6 119.95(5) . . ? C8 C7 C6 120.00(5) . . ? O2 C3 O1 128.35(5) . . ? O2 C3 O3 125.48(5) . . ? O1 C3 O3 106.16(4) . . ? C1 C1 C2 177.69(6) 2_565 . ? O1 C2 C1 110.67(4) . . ? O1 C2 H2A 107.7(10) . . ? C1 C2 H2A 111.5(9) . . ? O1 C2 H2B 104.5(9) . . ? C1 C2 H2B 112.7(8) . . ? H2A C2 H2B 109.5(13) . . ? F2 C6 C5 120.28(6) . . ? F2 C6 C7 119.78(6) . . ? C5 C6 C7 119.93(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 C3 O3 C4 C9 110.95(6) . . . . ? C3 O3 C4 C5 -73.23(7) . . . . ? F5 C9 C4 O3 -5.45(8) . . . . ? C8 C9 C4 O3 174.89(5) . . . . ? F5 C9 C4 C5 178.64(5) . . . . ? C8 C9 C4 C5 -1.02(8) . . . . ? F1 C5 C4 O3 4.96(8) . . . . ? C6 C5 C4 O3 -175.62(5) . . . . ? F1 C5 C4 C9 -179.21(5) . . . . ? C6 C5 C4 C9 0.21(8) . . . . ? F5 C9 C8 F4 0.69(9) . . . . ? C4 C9 C8 F4 -179.66(5) . . . . ? F5 C9 C8 C7 -178.91(5) . . . . ? C4 C9 C8 C7 0.75(9) . . . . ? F4 C8 C7 F3 0.56(8) . . . . ? C9 C8 C7 F3 -179.85(5) . . . . ? F4 C8 C7 C6 -179.26(5) . . . . ? C9 C8 C7 C6 0.34(8) . . . . ? C2 O1 C3 O2 3.67(8) . . . . ? C2 O1 C3 O3 -177.01(4) . . . . ? C4 O3 C3 O2 -2.03(8) . . . . ? C4 O3 C3 O1 178.62(4) . . . . ? C3 O1 C2 C1 78.69(6) . . . . ? F1 C5 C6 F2 0.93(10) . . . . ? C4 C5 C6 F2 -178.49(5) . . . . ? F1 C5 C6 C7 -179.72(5) . . . . ? C4 C5 C6 C7 0.87(9) . . . . ? F3 C7 C6 F2 -1.60(8) . . . . ? C8 C7 C6 F2 178.22(5) . . . . ? F3 C7 C6 C5 179.05(5) . . . . ? C8 C7 C6 C5 -1.14(8) . . . . ? #===END # Attachment '1n_acta.cif' # CIF-file generated for venia in space group P 1 #============================================================================== data_venia _database_code_depnum_ccdc_archive 'CCDC 784068' #TrackingRef '1n_acta.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'But-2-yne-1,4-diyl bis(2,3,4,5,6-pentafluorophenylcarbonate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H4 F10 O6' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C18 H4 F10 O6' _chemical_formula_iupac ? _chemical_formula_weight 506.21 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'A 2 -2ac' _symmetry_space_group_name_H-M 'A b a 2' _symmetry_Int_Tables_number 41 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,z 3 1/2-x,y,1/2+z 4 1/2+x,-y,1/2+z 5 x,1/2+y,1/2+z 6 -x,1/2-y,1/2+z 7 1/2-x,1/2+y,z 8 1/2+x,1/2-y,z _cell_length_a 16.3233(5) _cell_length_b 9.9385(4) _cell_length_c 10.9883(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1782.62(11) _cell_formula_units_Z 4 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used 6192 _cell_measurement_theta_min 4.66 _cell_measurement_theta_max 26.34 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 1.30 _exptl_crystal_size_mid 1.24 _exptl_crystal_size_min 1.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.89 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 0.729 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type none #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 90(1) _diffrn_radiation_wavelength 0.7 _diffrn_radiation_probe Neutron _diffrn_radiation_type Neutron _diffrn_radiation_source 'OPAL Uranium Reactor' _diffrn_radiation_monochromator nonmonochrmatic _diffrn_measurement_device_type 'KOALA-Laue diffractometer' _diffrn_measurement_method 'Laue patterns recorded from stationary crystal' _diffrn_standards_number '14 frames' _diffrn_standards_interval_count '10 degrees' _diffrn_standards_interval_time '60 minutes per frame' _diffrn_standards_decay_% 'not detemined' _diffrn_reflns_number 6192 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 26.34 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_max 0.572 _diffrn_measured_fraction_theta_full 0.572 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 870 # number of observed reflections (> n sig(I)) _reflns_number_gt 789 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-term LAUEGEN' _computing_cell_refinement 'X-term LAUEGEN' _computing_data_reduction 'X-term LAUEGEN' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0229P)^2^+7.1485P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens located _refine_ls_hydrogen_treatment mixed _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 10(10) _refine_ls_number_reflns 870 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0619 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.361 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.085 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 C9 C 0.1865(2) 0.1826(3) 1.04557(19) 0.0144(6) Uani 1 1 d . . . C5 C 0.13371(19) 0.4081(2) 1.04788(19) 0.0155(7) Uani 1 1 d . . . C4 C 0.16067(18) 0.2964(3) 0.9828(2) 0.0147(6) Uani 1 1 d . . . C8 C 0.1863(2) 0.1805(2) 1.17231(19) 0.0154(6) Uani 1 1 d . . . C7 C 0.15895(19) 0.2928(2) 1.2358(2) 0.0148(6) Uani 1 1 d . . . C3 C 0.09697(18) 0.2962(2) 0.7938(2) 0.0135(6) Uani 1 1 d . . . C1 C 0.01343(16) 0.4435(2) 0.5902(3) 0.0158(5) Uani 1 1 d . . . C2 C 0.04815(16) 0.30865(19) 0.5939(2) 0.0166(6) Uani 1 1 d . . . C6 C 0.1322(2) 0.4054(2) 1.1751(2) 0.0177(7) Uani 1 1 d . . . O3 O 0.1680(2) 0.3003(3) 0.8579(2) 0.0165(7) Uani 1 1 d . . . O1 O 0.1177(2) 0.3032(2) 0.6776(2) 0.0170(7) Uani 1 1 d . . . O2 O 0.0295(2) 0.2884(3) 0.8366(3) 0.0179(6) Uani 1 1 d . . . F5 F 0.2110(2) 0.0742(3) 0.9859(3) 0.0235(9) Uani 1 1 d . . . F4 F 0.2115(2) 0.0720(3) 1.2324(3) 0.0250(9) Uani 1 1 d . . . F3 F 0.1591(2) 0.2901(3) 1.3568(3) 0.0223(8) Uani 1 1 d . . . F1 F 0.1077(3) 0.5169(3) 0.9892(3) 0.0261(10) Uani 1 1 d . . . F2 F 0.1048(3) 0.5115(3) 1.2355(4) 0.0283(10) Uani 1 1 d . . . H2A H 0.0025(3) 0.2355(5) 0.6197(10) 0.0348(16) Uani 1 1 d . . . H2B H 0.0727(4) 0.2782(6) 0.5058(5) 0.0333(15) 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 C9 0.013(2) 0.0165(11) 0.0141(11) -0.0015(10) -0.0002(10) 0.0025(10) C5 0.018(2) 0.0129(11) 0.0159(11) -0.0012(9) 0.0007(11) 0.0004(11) C4 0.014(2) 0.0161(12) 0.0138(11) 0.0031(10) 0.0011(11) 0.0008(10) C8 0.015(2) 0.0174(11) 0.0138(11) 0.0011(11) -0.0011(11) 0.0005(10) C7 0.012(2) 0.0198(11) 0.0129(11) 0.0001(11) -0.0004(10) -0.0014(11) C3 0.008(2) 0.0194(10) 0.0133(10) 0.0004(9) 0.0007(12) 0.0017(9) C1 0.0127(16) 0.0156(8) 0.0191(11) 0.0007(9) 0.0019(11) 0.0005(8) C2 0.0159(18) 0.0184(9) 0.0154(11) -0.0033(11) 0.0018(11) 0.0027(9) C6 0.013(2) 0.0183(11) 0.0216(13) -0.0053(11) 0.0002(11) -0.0035(10) O3 0.014(2) 0.0233(14) 0.0122(13) 0.0042(13) 0.0006(12) 0.0007(11) O1 0.015(2) 0.0204(13) 0.0161(12) 0.0030(10) 0.0041(11) 0.0026(13) O2 0.012(2) 0.0266(13) 0.0147(11) 0.0029(11) 0.0026(14) 0.0002(14) F5 0.029(3) 0.0210(12) 0.0206(15) -0.0022(12) -0.0060(15) 0.0087(14) F4 0.027(3) 0.0256(14) 0.0221(15) 0.0055(14) -0.0070(14) 0.0021(14) F3 0.013(3) 0.0410(17) 0.0126(15) -0.0025(15) 0.0026(13) -0.0010(15) F1 0.032(3) 0.0159(14) 0.0302(19) 0.0066(12) -0.0005(16) 0.0064(14) F2 0.032(3) 0.0248(16) 0.0280(16) -0.0112(14) -0.0015(17) 0.0026(15) H2A 0.024(4) 0.034(2) 0.046(4) -0.002(3) -0.005(3) -0.004(2) H2B 0.036(5) 0.046(3) 0.018(3) -0.003(2) 0.001(3) 0.009(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 C9 F5 1.323(4) . ? C9 C4 1.390(4) . ? C9 C8 1.393(3) . ? C5 F1 1.329(4) . ? C5 C4 1.392(4) . ? C5 C6 1.398(3) . ? C4 O3 1.378(4) . ? C8 F4 1.330(4) . ? C8 C7 1.389(4) . ? C7 F3 1.330(4) . ? C7 C6 1.374(4) . ? C3 O2 1.201(5) . ? C3 O1 1.322(3) . ? C3 O3 1.358(4) . ? C1 C1 1.205(4) 2_565 ? C1 C2 1.456(3) . ? C2 O1 1.461(4) . ? C2 H2A 1.079(6) . ? C2 H2B 1.091(5) . ? C6 F2 1.324(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 F5 C9 C4 120.5(2) . . ? F5 C9 C8 119.0(3) . . ? C4 C9 C8 120.5(3) . . ? F1 C5 C4 120.1(2) . . ? F1 C5 C6 119.7(3) . . ? C4 C5 C6 120.2(3) . . ? O3 C4 C9 119.4(2) . . ? O3 C4 C5 121.1(2) . . ? C9 C4 C5 119.3(2) . . ? F4 C8 C7 120.1(2) . . ? F4 C8 C9 120.5(3) . . ? C7 C8 C9 119.4(3) . . ? F3 C7 C6 120.2(3) . . ? F3 C7 C8 119.0(3) . . ? C6 C7 C8 120.8(2) . . ? O2 C3 O1 128.0(3) . . ? O2 C3 O3 125.6(3) . . ? O1 C3 O3 106.3(3) . . ? C1 C1 C2 177.8(3) 2_565 . ? C1 C2 O1 110.7(2) . . ? C1 C2 H2A 111.0(3) . . ? O1 C2 H2A 110.3(5) . . ? C1 C2 H2B 111.9(3) . . ? O1 C2 H2B 105.3(4) . . ? H2A C2 H2B 107.5(6) . . ? F2 C6 C7 120.8(3) . . ? F2 C6 C5 119.4(3) . . ? C7 C6 C5 119.7(3) . . ? C3 O3 C4 116.2(3) . . ? C3 O1 C2 114.3(3) . . ? 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 F5 C9 C4 O3 -6.2(5) . . . . ? C8 C9 C4 O3 174.5(3) . . . . ? F5 C9 C4 C5 178.7(3) . . . . ? C8 C9 C4 C5 -0.6(5) . . . . ? F1 C5 C4 O3 6.0(5) . . . . ? C6 C5 C4 O3 -175.4(3) . . . . ? F1 C5 C4 C9 -179.0(3) . . . . ? C6 C5 C4 C9 -0.4(5) . . . . ? F5 C9 C8 F4 1.0(6) . . . . ? C4 C9 C8 F4 -179.6(3) . . . . ? F5 C9 C8 C7 -178.5(3) . . . . ? C4 C9 C8 C7 0.8(5) . . . . ? F4 C8 C7 F3 0.7(5) . . . . ? C9 C8 C7 F3 -179.8(3) . . . . ? F4 C8 C7 C6 -179.5(3) . . . . ? C9 C8 C7 C6 0.0(5) . . . . ? F3 C7 C6 F2 -1.4(5) . . . . ? C8 C7 C6 F2 178.8(4) . . . . ? F3 C7 C6 C5 178.8(3) . . . . ? C8 C7 C6 C5 -1.0(5) . . . . ? F1 C5 C6 F2 0.0(6) . . . . ? C4 C5 C6 F2 -178.6(3) . . . . ? F1 C5 C6 C7 179.8(3) . . . . ? C4 C5 C6 C7 1.2(5) . . . . ? O2 C3 O3 C4 -0.6(4) . . . . ? O1 C3 O3 C4 179.0(2) . . . . ? C9 C4 O3 C3 110.6(3) . . . . ? C5 C4 O3 C3 -74.4(4) . . . . ? O2 C3 O1 C2 3.3(4) . . . . ? O3 C3 O1 C2 -176.3(2) . . . . ? C1 C2 O1 C3 78.6(3) . . . . ? #===END # Attachment '2_acta.cif' # CIF-file generated for veap-f150 in P21/c #14 #============================================================================== data_veap-f150 _database_code_depnum_ccdc_archive 'CCDC 784069' #TrackingRef '2_acta.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'But-2-yne-1,4-diyl bis(4-fluorophenylcarbonate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 F2 O6' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C18 H12 F2 O6' _chemical_formula_iupac ? _chemical_formula_weight 362.28 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 14.2326(14) _cell_length_b 4.0156(5) _cell_length_c 13.8877(12) _cell_angle_alpha 90 _cell_angle_beta 98.500(9) _cell_angle_gamma 90 _cell_volume 784.99(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9118 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 25.99 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.131 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.9619 _exptl_absorpt_correction_T_max 0.9744 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 9118 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1530 # number of observed reflections (> n sig(I)) _reflns_number_gt 1191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0513P)^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 1530 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.193 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.041 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.36426(7) 0.0441(2) 0.13345(7) 0.0249(3) Uani 1 1 d . . . O3 O 0.25294(8) -0.0262(3) 0.22114(7) 0.0305(3) Uani 1 1 d . . . F1 F 0.08346(7) 0.1859(3) 0.54567(6) 0.0394(3) Uani 1 1 d . . . C4 C 0.21114(10) 0.0312(4) 0.30630(11) 0.0236(4) Uani 1 1 d . . . C1 C 0.48364(10) 0.0624(3) 0.03255(10) 0.0217(3) Uani 1 1 d . . . C3 C 0.33459(10) 0.1348(4) 0.21635(10) 0.0213(3) Uani 1 1 d . . . O2 O 0.37343(8) 0.3232(3) 0.27476(8) 0.0390(3) Uani 1 1 d . . . C5 C 0.12652(11) 0.2025(4) 0.29583(11) 0.0265(4) Uani 1 1 d . . . C2 C 0.44894(11) 0.2209(4) 0.11525(11) 0.0237(4) Uani 1 1 d . . . C8 C 0.20908(11) -0.0458(4) 0.47583(12) 0.0272(4) Uani 1 1 d . . . C9 C 0.25316(11) -0.0977(4) 0.39453(12) 0.0269(4) Uani 1 1 d . . . C7 C 0.12562(11) 0.1288(4) 0.46522(11) 0.0257(4) Uani 1 1 d . . . C6 C 0.08221(11) 0.2523(4) 0.37713(11) 0.0278(4) Uani 1 1 d . . . H2A H 0.4980(12) 0.213(4) 0.1759(12) 0.031(4) Uiso 1 1 d . . . H5 H 0.1001(13) 0.293(4) 0.2350(13) 0.036(5) Uiso 1 1 d . . . H2B H 0.4331(11) 0.448(5) 0.1017(12) 0.032(5) Uiso 1 1 d . . . H8 H 0.3102(12) -0.220(4) 0.3993(12) 0.032(4) Uiso 1 1 d . . . H7 H 0.2325(12) -0.138(4) 0.5370(13) 0.036(5) Uiso 1 1 d . . . H6 H 0.0273(13) 0.375(4) 0.3736(12) 0.036(5) 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 0.0261(6) 0.0289(6) 0.0228(6) -0.0052(4) 0.0134(4) -0.0057(4) O3 0.0280(6) 0.0430(7) 0.0239(6) -0.0110(5) 0.0147(5) -0.0115(5) F1 0.0399(6) 0.0586(7) 0.0238(5) -0.0071(5) 0.0177(4) -0.0005(5) C4 0.0251(9) 0.0283(8) 0.0198(8) -0.0067(6) 0.0112(6) -0.0074(6) C1 0.0223(8) 0.0214(8) 0.0225(8) 0.0036(6) 0.0074(6) -0.0006(6) C3 0.0222(8) 0.0228(7) 0.0201(7) 0.0001(6) 0.0067(6) 0.0007(6) O2 0.0382(7) 0.0506(8) 0.0322(7) -0.0205(6) 0.0189(5) -0.0184(6) C5 0.0283(9) 0.0314(9) 0.0200(8) 0.0010(7) 0.0038(6) -0.0033(7) C2 0.0255(8) 0.0225(8) 0.0259(8) -0.0025(7) 0.0134(7) -0.0024(6) C8 0.0299(9) 0.0314(9) 0.0202(8) 0.0018(7) 0.0038(7) -0.0037(7) C9 0.0234(9) 0.0304(9) 0.0279(8) -0.0030(7) 0.0070(7) -0.0003(7) C7 0.0287(9) 0.0305(8) 0.0206(8) -0.0053(7) 0.0125(6) -0.0060(7) C6 0.0232(9) 0.0334(9) 0.0281(9) -0.0017(7) 0.0078(7) 0.0016(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.3343(16) . ? O1 C2 1.4527(17) . ? O3 C3 1.3399(18) . ? O3 C4 1.4191(17) . ? F1 C7 1.3635(16) . ? C4 C5 1.376(2) . ? C4 C9 1.382(2) . ? C1 C1 1.187(3) 3_655 ? C1 C2 1.4614(19) . ? C3 O2 1.1846(17) . ? C5 C6 1.387(2) . ? C5 H5 0.946(18) . ? C2 H2A 1.011(17) . ? C2 H2B 0.952(18) . ? C8 C7 1.368(2) . ? C8 C9 1.386(2) . ? C8 H7 0.942(17) . ? C9 H8 0.943(17) . ? C7 C6 1.379(2) . ? C6 H6 0.920(18) . ? 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 C3 O1 C2 113.16(11) . . ? C3 O3 C4 115.88(11) . . ? C5 C4 C9 122.57(14) . . ? C5 C4 O3 117.47(13) . . ? C9 C4 O3 119.88(13) . . ? C1 C1 C2 176.7(2) 3_655 . ? O2 C3 O1 126.15(13) . . ? O2 C3 O3 126.47(13) . . ? O1 C3 O3 107.37(12) . . ? C4 C5 C6 118.84(14) . . ? C4 C5 H5 120.9(10) . . ? C6 C5 H5 120.2(10) . . ? O1 C2 C1 108.02(12) . . ? O1 C2 H2A 109.1(9) . . ? C1 C2 H2A 111.6(9) . . ? O1 C2 H2B 109.0(10) . . ? C1 C2 H2B 111.0(10) . . ? H2A C2 H2B 108.1(13) . . ? C7 C8 C9 118.66(15) . . ? C7 C8 H7 119.0(10) . . ? C9 C8 H7 122.3(10) . . ? C4 C9 C8 118.49(15) . . ? C4 C9 H8 120.8(10) . . ? C8 C9 H8 120.7(10) . . ? F1 C7 C8 118.56(14) . . ? F1 C7 C6 118.22(14) . . ? C8 C7 C6 123.22(14) . . ? C7 C6 C5 118.20(15) . . ? C7 C6 H6 120.4(10) . . ? C5 C6 H6 121.3(10) . . ? 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 C3 O3 C4 C5 112.41(15) . . . . ? C3 O3 C4 C9 -70.73(18) . . . . ? C2 O1 C3 O2 -4.4(2) . . . . ? C2 O1 C3 O3 175.52(12) . . . . ? C4 O3 C3 O2 -1.7(2) . . . . ? C4 O3 C3 O1 178.32(11) . . . . ? C9 C4 C5 C6 1.0(2) . . . . ? O3 C4 C5 C6 177.75(13) . . . . ? C3 O1 C2 C1 170.45(12) . . . . ? C5 C4 C9 C8 -1.4(2) . . . . ? O3 C4 C9 C8 -178.10(13) . . . . ? C7 C8 C9 C4 0.4(2) . . . . ? C9 C8 C7 F1 -178.57(13) . . . . ? C9 C8 C7 C6 0.9(2) . . . . ? F1 C7 C6 C5 178.15(13) . . . . ? C8 C7 C6 C5 -1.4(2) . . . . ? C4 C5 C6 C7 0.4(2) . . . . ? #===END # Attachment '3_acta.cif' # CIF-file generated for veapfa150 in P2(1)/c #============================================================================== data_veapfa150 _database_code_depnum_ccdc_archive 'CCDC 784070' #TrackingRef '3_acta.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'But-2-yne-1,4-diyl bis(2,3,4,5,6-pentafluorophenylcarbamate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H6 F10 N2 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C18 H6 F10 N2 O4' _chemical_formula_iupac ? _chemical_formula_weight 504.25 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 6.8592(5) _cell_length_b 4.8508(3) _cell_length_c 27.201(2) _cell_angle_alpha 90 _cell_angle_beta 102.247(6) _cell_angle_gamma 90 _cell_volume 884.46(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 10202 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 26.00 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.893 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.202 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.9606 _exptl_absorpt_correction_T_max 0.9606 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 10202 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1731 # number of observed reflections (> n sig(I)) _reflns_number_gt 1245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0440P)^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 1731 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.199 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.046 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 F5 F 0.51573(15) 0.8781(2) 0.09380(4) 0.0287(3) Uani 1 1 d . . . F1 F 0.27533(15) 0.1462(2) 0.17873(4) 0.0321(3) Uani 1 1 d . . . F4 F 0.87885(16) 0.8161(2) 0.15296(5) 0.0372(3) Uani 1 1 d . . . F2 F 0.64169(17) 0.0725(2) 0.23479(4) 0.0379(3) Uani 1 1 d . . . O2 O 0.11436(19) 0.1217(2) 0.07562(5) 0.0273(3) Uani 1 1 d . . . O1 O -0.09808(17) 0.4774(2) 0.05409(5) 0.0257(3) Uani 1 1 d . . . F3 F 0.94759(16) 0.4018(2) 0.22229(5) 0.0431(4) Uani 1 1 d . . . N1 N 0.1949(2) 0.5588(3) 0.10363(6) 0.0234(4) Uani 1 1 d . . . C4 C 0.3854(3) 0.5077(4) 0.13291(7) 0.0201(4) Uani 1 1 d . . . C6 C 0.6115(3) 0.2689(4) 0.19932(7) 0.0254(5) Uani 1 1 d . . . C5 C 0.4230(3) 0.3063(4) 0.16995(7) 0.0226(4) Uani 1 1 d . . . C9 C 0.5445(3) 0.6735(4) 0.12799(7) 0.0227(4) Uani 1 1 d . . . C2 C -0.2413(3) 0.2845(4) 0.02614(9) 0.0256(5) Uani 1 1 d . . . C3 C 0.0749(3) 0.3631(4) 0.07767(7) 0.0219(4) Uani 1 1 d . . . C7 C 0.7663(3) 0.4364(4) 0.19342(7) 0.0268(5) Uani 1 1 d . . . C8 C 0.7319(3) 0.6428(4) 0.15798(8) 0.0263(5) Uani 1 1 d . . . C1 C -0.4254(3) 0.4388(4) 0.00748(7) 0.0247(4) Uani 1 1 d . . . H2A H -0.186(3) 0.209(4) -0.0001(7) 0.018(5) Uiso 1 1 d . . . H1N H 0.165(3) 0.709(4) 0.0982(8) 0.024(6) Uiso 1 1 d . . . H2B H -0.266(3) 0.139(4) 0.0470(8) 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 F5 0.0306(6) 0.0214(6) 0.0349(7) 0.0030(5) 0.0086(5) -0.0032(5) F1 0.0275(6) 0.0302(6) 0.0386(7) 0.0077(5) 0.0069(5) -0.0055(5) F4 0.0224(6) 0.0378(7) 0.0522(8) -0.0066(6) 0.0098(5) -0.0104(5) F2 0.0395(7) 0.0384(7) 0.0313(7) 0.0104(5) -0.0022(5) 0.0046(6) O2 0.0261(7) 0.0142(7) 0.0382(9) 0.0019(6) -0.0008(6) 0.0013(6) O1 0.0188(7) 0.0191(6) 0.0348(8) -0.0008(6) -0.0047(6) 0.0018(6) F3 0.0249(6) 0.0465(7) 0.0498(8) -0.0032(6) -0.0105(6) 0.0030(6) N1 0.0201(8) 0.0125(8) 0.0350(10) 0.0007(7) -0.0003(7) 0.0021(7) C4 0.0201(9) 0.0165(9) 0.0236(10) -0.0044(8) 0.0045(8) -0.0001(8) C6 0.0293(11) 0.0234(10) 0.0221(11) -0.0014(8) 0.0021(8) 0.0039(9) C5 0.0218(10) 0.0200(10) 0.0276(11) -0.0023(8) 0.0089(8) -0.0017(8) C9 0.0257(10) 0.0179(10) 0.0250(11) -0.0015(8) 0.0065(8) 0.0012(8) C2 0.0208(10) 0.0240(10) 0.0290(12) -0.0010(9) -0.0014(8) -0.0025(9) C3 0.0202(10) 0.0199(10) 0.0251(11) 0.0036(8) 0.0037(8) 0.0006(8) C7 0.0188(9) 0.0280(10) 0.0304(11) -0.0081(9) -0.0019(8) 0.0040(9) C8 0.0190(10) 0.0257(10) 0.0349(12) -0.0106(9) 0.0074(8) -0.0054(9) C1 0.0228(9) 0.0267(11) 0.0233(10) -0.0027(8) 0.0015(8) -0.0049(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 F5 C9 1.346(2) . ? F1 C5 1.337(2) . ? F4 C8 1.342(2) . ? F2 C6 1.341(2) . ? O2 C3 1.206(2) . ? O1 C3 1.343(2) . ? O1 C2 1.450(2) . ? F3 C7 1.333(2) . ? N1 C3 1.353(2) . ? N1 C4 1.400(2) . ? N1 H1N 0.762(18) . ? C4 C9 1.385(3) . ? C4 C5 1.388(2) . ? C6 C7 1.373(3) . ? C6 C5 1.380(2) . ? C9 C8 1.376(3) . ? C2 C1 1.463(3) . ? C2 H2A 0.948(19) . ? C2 H2B 0.94(2) . ? C7 C8 1.375(3) . ? C1 C1 1.179(4) 3_465 ? 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 C3 O1 C2 114.57(14) . . ? C3 N1 C4 124.29(16) . . ? C3 N1 H1N 117.2(15) . . ? C4 N1 H1N 117.6(15) . . ? C9 C4 C5 116.74(16) . . ? C9 C4 N1 120.09(16) . . ? C5 C4 N1 123.03(16) . . ? F2 C6 C7 119.97(16) . . ? F2 C6 C5 119.51(17) . . ? C7 C6 C5 120.49(17) . . ? F1 C5 C6 118.19(16) . . ? F1 C5 C4 120.49(16) . . ? C6 C5 C4 121.31(17) . . ? F5 C9 C8 118.11(16) . . ? F5 C9 C4 119.46(16) . . ? C8 C9 C4 122.40(18) . . ? O1 C2 C1 106.90(15) . . ? O1 C2 H2A 108.1(11) . . ? C1 C2 H2A 112.9(11) . . ? O1 C2 H2B 110.8(12) . . ? C1 C2 H2B 109.9(12) . . ? H2A C2 H2B 108.3(16) . . ? O2 C3 O1 124.25(16) . . ? O2 C3 N1 126.01(17) . . ? O1 C3 N1 109.74(15) . . ? F3 C7 C6 120.30(17) . . ? F3 C7 C8 120.30(17) . . ? C6 C7 C8 119.39(17) . . ? F4 C8 C7 120.44(16) . . ? F4 C8 C9 119.94(17) . . ? C7 C8 C9 119.61(17) . . ? C1 C1 C2 179.4(3) 3_465 . ? 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 C3 N1 C4 C9 132.1(2) . . . . ? C3 N1 C4 C5 -52.3(3) . . . . ? F2 C6 C5 F1 1.1(3) . . . . ? C7 C6 C5 F1 -176.95(16) . . . . ? F2 C6 C5 C4 179.86(16) . . . . ? C7 C6 C5 C4 1.8(3) . . . . ? C9 C4 C5 F1 176.84(16) . . . . ? N1 C4 C5 F1 1.1(3) . . . . ? C9 C4 C5 C6 -1.9(3) . . . . ? N1 C4 C5 C6 -177.55(17) . . . . ? C5 C4 C9 F5 -177.90(16) . . . . ? N1 C4 C9 F5 -2.1(3) . . . . ? C5 C4 C9 C8 0.1(3) . . . . ? N1 C4 C9 C8 175.93(17) . . . . ? C3 O1 C2 C1 174.43(16) . . . . ? C2 O1 C3 O2 1.6(3) . . . . ? C2 O1 C3 N1 -178.26(16) . . . . ? C4 N1 C3 O2 -0.7(3) . . . . ? C4 N1 C3 O1 179.12(17) . . . . ? F2 C6 C7 F3 1.1(3) . . . . ? C5 C6 C7 F3 179.17(17) . . . . ? F2 C6 C7 C8 -177.95(17) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? F3 C7 C8 F4 -1.8(3) . . . . ? C6 C7 C8 F4 177.26(17) . . . . ? F3 C7 C8 C9 179.11(17) . . . . ? C6 C7 C8 C9 -1.8(3) . . . . ? F5 C9 C8 F4 0.7(3) . . . . ? C4 C9 C8 F4 -177.35(16) . . . . ? F5 C9 C8 C7 179.77(16) . . . . ? C4 C9 C8 C7 1.8(3) . . . . ? #===END # Attachment '4_acta.cif' # CIF-file generated for vaaalt_m in P2(1)/n #============================================================================== data_vaaalt_m _database_code_depnum_ccdc_archive 'CCDC 784071' #TrackingRef '4_acta.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'Hexa-2,4-diyne-1,6-diyl bis(2,3,4,5,6-pentafluorophenylcarbonate)' ; _chemical_name_common ;'Hexa-2,4-diyne-1,6-diyl bis(2,3,4,5,6- pentafluorophenylcarbonate)' ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H4 F10 O6' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C20 H4 F10 O6' _chemical_formula_iupac ? _chemical_formula_weight 530.23 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 5.8951(9) _cell_length_b 10.1943(16) _cell_length_c 17.245(2) _cell_angle_alpha 90 _cell_angle_beta 108.115(5) _cell_angle_gamma 90 _cell_volume 985.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9757 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.00 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.191 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.9274 _exptl_absorpt_correction_T_max 0.9627 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 9757 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1937 # number of observed reflections (> n sig(I)) _reflns_number_gt 1538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0464P)^2^+0.5750P] 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 1937 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.268 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.055 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O3 O -0.4780(3) -0.19900(18) -0.73643(10) 0.0310(4) Uani 1 1 d . . . O2 O -0.7292(3) -0.19507(17) -0.86663(10) 0.0324(4) Uani 1 1 d . . . O1 O -0.3249(3) -0.19879(16) -0.83362(10) 0.0269(4) Uani 1 1 d . . . F2 F -1.0983(3) 0.02333(17) -0.66636(11) 0.0500(5) Uani 1 1 d . . . F1 F -0.7704(3) 0.01883(15) -0.74720(10) 0.0419(4) Uani 1 1 d . . . F3 F -1.1491(3) -0.18830(19) -0.57714(10) 0.0502(5) Uani 1 1 d . . . C5 C -0.6639(4) -0.1977(2) -0.70363(14) 0.0258(5) Uani 1 1 d . . . F4 F -0.8826(3) -0.40672(17) -0.57307(10) 0.0515(5) Uani 1 1 d . . . F5 F -0.5566(3) -0.41086(15) -0.65395(10) 0.0450(5) Uani 1 1 d . . . C4 C -0.5339(4) -0.1973(2) -0.81954(15) 0.0253(5) Uani 1 1 d . . . C2 C -0.4149(4) -0.3327(2) -0.95396(14) 0.0256(5) Uani 1 1 d . . . C6 C -0.8013(4) -0.0870(2) -0.70547(15) 0.0280(6) Uani 1 1 d . . . C10 C -0.6946(4) -0.3043(2) -0.65897(15) 0.0292(6) Uani 1 1 d . . . C8 C -0.9925(4) -0.1914(3) -0.61916(15) 0.0333(6) Uani 1 1 d . . . C3 C -0.3409(5) -0.2030(3) -0.91917(15) 0.0278(6) Uani 1 1 d . . . C9 C -0.8579(5) -0.3020(3) -0.61711(15) 0.0328(6) Uani 1 1 d . . . C7 C -0.9659(5) -0.0840(3) -0.66401(16) 0.0320(6) Uani 1 1 d . . . C1 C -0.4693(4) -0.4388(2) -0.98285(14) 0.0255(5) Uani 1 1 d . . . H2A H -0.174(5) -0.184(2) -0.9177(14) 0.023(6) Uiso 1 1 d . . . H2B H -0.447(5) -0.140(3) -0.9470(16) 0.027(7) 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 O3 0.0209(9) 0.0477(11) 0.0257(9) -0.0033(8) 0.0091(7) 0.0000(8) O2 0.0238(9) 0.0407(11) 0.0315(10) -0.0022(8) 0.0068(8) -0.0025(8) O1 0.0246(9) 0.0311(10) 0.0267(9) -0.0055(7) 0.0108(7) -0.0036(7) F2 0.0428(10) 0.0515(11) 0.0561(11) -0.0091(8) 0.0157(8) 0.0206(8) F1 0.0490(10) 0.0291(9) 0.0484(10) 0.0059(7) 0.0161(8) 0.0008(7) F3 0.0319(9) 0.0899(14) 0.0351(9) -0.0056(9) 0.0196(7) 0.0016(9) C5 0.0218(12) 0.0303(14) 0.0248(12) -0.0070(10) 0.0065(9) -0.0023(10) F4 0.0592(12) 0.0505(11) 0.0482(10) 0.0115(8) 0.0219(9) -0.0102(9) F5 0.0557(11) 0.0307(9) 0.0515(10) 0.0014(7) 0.0211(8) 0.0129(8) C4 0.0265(13) 0.0206(12) 0.0296(13) -0.0024(10) 0.0097(11) -0.0018(10) C2 0.0250(13) 0.0295(13) 0.0238(12) 0.0020(10) 0.0100(10) 0.0022(10) C6 0.0263(13) 0.0261(13) 0.0287(13) -0.0013(11) 0.0041(10) -0.0022(10) C10 0.0298(13) 0.0258(14) 0.0311(13) -0.0052(11) 0.0082(11) -0.0005(11) C8 0.0209(12) 0.0531(18) 0.0265(13) -0.0087(12) 0.0083(10) -0.0041(12) C3 0.0300(14) 0.0288(14) 0.0271(13) -0.0005(11) 0.0125(11) -0.0042(11) C9 0.0357(15) 0.0343(15) 0.0277(13) 0.0002(11) 0.0089(11) -0.0098(12) C7 0.0261(13) 0.0349(15) 0.0332(14) -0.0088(12) 0.0067(11) 0.0073(11) C1 0.0243(13) 0.0317(14) 0.0216(12) 0.0020(10) 0.0087(10) 0.0014(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 O3 C4 1.367(3) . ? O3 C5 1.381(3) . ? O2 C4 1.185(3) . ? O1 C4 1.328(3) . ? O1 C3 1.449(3) . ? F2 C7 1.338(3) . ? F1 C6 1.340(3) . ? F3 C8 1.340(3) . ? C5 C10 1.376(4) . ? C5 C6 1.383(3) . ? F4 C9 1.344(3) . ? F5 C10 1.343(3) . ? C2 C1 1.192(3) . ? C2 C3 1.461(4) . ? C6 C7 1.373(4) . ? C10 C9 1.371(4) . ? C8 C9 1.373(4) . ? C8 C7 1.377(4) . ? C3 H2A 0.99(3) . ? C3 H2B 0.92(3) . ? C1 C1 1.380(5) 3_443 ? 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 C4 O3 C5 117.79(18) . . ? C4 O1 C3 114.59(19) . . ? C10 C5 O3 118.7(2) . . ? C10 C5 C6 118.6(2) . . ? O3 C5 C6 122.1(2) . . ? O2 C4 O1 129.4(2) . . ? O2 C4 O3 125.8(2) . . ? O1 C4 O3 104.87(19) . . ? C1 C2 C3 178.1(3) . . ? F1 C6 C7 119.9(2) . . ? F1 C6 C5 119.5(2) . . ? C7 C6 C5 120.6(2) . . ? F5 C10 C9 119.4(2) . . ? F5 C10 C5 119.5(2) . . ? C9 C10 C5 121.1(2) . . ? F3 C8 C9 119.7(2) . . ? F3 C8 C7 120.2(2) . . ? C9 C8 C7 120.1(2) . . ? O1 C3 C2 111.2(2) . . ? O1 C3 H2A 102.6(14) . . ? C2 C3 H2A 110.7(14) . . ? O1 C3 H2B 109.1(16) . . ? C2 C3 H2B 110.6(16) . . ? H2A C3 H2B 112(2) . . ? F4 C9 C10 120.0(2) . . ? F4 C9 C8 120.2(2) . . ? C10 C9 C8 119.7(2) . . ? F2 C7 C6 120.2(2) . . ? F2 C7 C8 120.0(2) . . ? C6 C7 C8 119.8(2) . . ? C2 C1 C1 179.2(3) . 3_443 ? 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 C4 O3 C5 C10 116.2(2) . . . . ? C4 O3 C5 C6 -72.0(3) . . . . ? C3 O1 C4 O2 -2.4(4) . . . . ? C3 O1 C4 O3 177.48(18) . . . . ? C5 O3 C4 O2 -0.2(3) . . . . ? C5 O3 C4 O1 179.87(19) . . . . ? C10 C5 C6 F1 178.6(2) . . . . ? O3 C5 C6 F1 6.8(3) . . . . ? C10 C5 C6 C7 -0.4(4) . . . . ? O3 C5 C6 C7 -172.2(2) . . . . ? O3 C5 C10 F5 -5.4(3) . . . . ? C6 C5 C10 F5 -177.5(2) . . . . ? O3 C5 C10 C9 172.3(2) . . . . ? C6 C5 C10 C9 0.2(4) . . . . ? C4 O1 C3 C2 -73.5(3) . . . . ? F5 C10 C9 F4 -1.5(4) . . . . ? C5 C10 C9 F4 -179.2(2) . . . . ? F5 C10 C9 C8 177.3(2) . . . . ? C5 C10 C9 C8 -0.4(4) . . . . ? F3 C8 C9 F4 -0.1(4) . . . . ? C7 C8 C9 F4 179.7(2) . . . . ? F3 C8 C9 C10 -178.9(2) . . . . ? C7 C8 C9 C10 0.9(4) . . . . ? F1 C6 C7 F2 1.2(4) . . . . ? C5 C6 C7 F2 -179.8(2) . . . . ? F1 C6 C7 C8 -178.1(2) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? F3 C8 C7 F2 -0.6(4) . . . . ? C9 C8 C7 F2 179.6(2) . . . . ? F3 C8 C7 C6 178.6(2) . . . . ? C9 C8 C7 C6 -1.2(4) . . . . ? #===END