# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #TrackingRef '246trifphenol_5.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Jan 29 15:14:15 2013' _audit_creation_method 'PLATON option' _audit_update_record ; ; #===END # Attachment 'phenol_1.cif' # CIF-file generated for vabalt in Pccn #============================================================================== #=============================================================================== data_vabalt #TrackingRef 'phenol_1.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'hexa-2,4-diyne-1,6-diyl bis(phenylcarbonate)' ; _chemical_name_common "'hexa-2,4-diyne-1,6-diyl bis(phenylcarbonate)'" _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 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 H14 O6' _chemical_formula_iupac ? _chemical_formula_weight 350.31 _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' 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 '-P 2ab 2ac' _symmetry_space_group_name_H-M 'P c c n' _symmetry_Int_Tables_number 56 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2-y,z 3 1/2+x,-y,1/2-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,1/2+y,-z 7 1/2-x,y,1/2+z 8 x,1/2-y,1/2+z _cell_length_a 9.5387(15) _cell_length_b 23.208(4) _cell_length_c 7.4056(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1639.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 15969 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 26.37 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_process_details 'Apex2 (Bruker)' _exptl_crystal_density_meas_temp ? #=============================================================================== # 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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker kappa apex2 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 15969 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1674 # number of observed reflections (> n sig(I)) _reflns_number_gt 1284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa Apex2' _computing_cell_refinement Apex2 _computing_data_reduction SAINT32 _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^)+(0.0498P)^2^+0.0089P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1674 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.188 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.036 #=============================================================================== # 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 0.88082(8) 0.69193(3) 0.11025(10) 0.0228(2) Uani 1 1 d . . . O3 O 0.88966(8) 0.65262(3) 0.37333(11) 0.0255(2) Uani 1 1 d . . . O2 O 1.02020(8) 0.61388(3) 0.14774(11) 0.0292(2) Uani 1 1 d . . . C2 C 1.06787(12) 0.71871(5) -0.09038(16) 0.0221(3) Uani 1 1 d . . . C4 C 0.93999(11) 0.64889(5) 0.20391(16) 0.0208(3) Uani 1 1 d . . . C5 C 0.94546(12) 0.61266(4) 0.49920(15) 0.0212(3) Uani 1 1 d . . . C1 C 1.18329(11) 0.73853(4) -0.09781(15) 0.0213(3) Uani 1 1 d . . . C3 C 0.92624(12) 0.69491(5) -0.07667(15) 0.0235(3) Uani 1 1 d . . . H3A H 0.8618 0.7189 -0.1446 0.028 Uiso 1 1 calc R . . H3B H 0.9247 0.6566 -0.1290 0.028 Uiso 1 1 calc R . . C9 C 1.13153(12) 0.58107(5) 0.68857(17) 0.0265(3) Uani 1 1 d . . . H9 H 1.2233 0.5844 0.7298 0.032 Uiso 1 1 calc R . . C6 C 0.85737(12) 0.57123(5) 0.56684(16) 0.0250(3) Uani 1 1 d . . . H6 H 0.7655 0.5682 0.5260 0.030 Uiso 1 1 calc R . . C10 C 1.08196(12) 0.61844(5) 0.55698(16) 0.0238(3) Uani 1 1 d . . . H10 H 1.1397 0.6468 0.5088 0.029 Uiso 1 1 calc R . . C7 C 0.90853(13) 0.53384(5) 0.69766(17) 0.0284(3) Uani 1 1 d . . . H7 H 0.8507 0.5052 0.7445 0.034 Uiso 1 1 calc R . . C8 C 1.04482(13) 0.53897(5) 0.75843(17) 0.0278(3) Uani 1 1 d . . . H8 H 1.0783 0.5140 0.8467 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0211(4) 0.0252(4) 0.0222(5) 0.0026(3) 0.0007(3) 0.0026(3) O3 0.0254(5) 0.0304(5) 0.0207(5) 0.0022(3) 0.0034(3) 0.0075(3) O2 0.0319(5) 0.0308(5) 0.0250(5) -0.0003(4) 0.0042(4) 0.0110(4) C2 0.0248(6) 0.0211(6) 0.0205(7) 0.0015(5) -0.0012(5) 0.0008(5) C4 0.0175(6) 0.0223(6) 0.0225(7) -0.0010(5) -0.0006(5) -0.0015(5) C5 0.0239(6) 0.0215(6) 0.0181(6) -0.0011(5) 0.0031(5) 0.0044(5) C1 0.0239(6) 0.0199(6) 0.0203(6) -0.0001(5) -0.0008(5) 0.0015(5) C3 0.0206(6) 0.0283(6) 0.0216(7) 0.0033(5) -0.0019(5) -0.0019(5) C9 0.0222(6) 0.0274(6) 0.0300(7) -0.0020(5) -0.0016(5) 0.0019(5) C6 0.0192(6) 0.0297(6) 0.0261(7) -0.0051(5) 0.0016(5) -0.0026(5) C10 0.0229(6) 0.0204(6) 0.0281(7) 0.0011(5) 0.0045(5) -0.0017(5) C7 0.0291(7) 0.0239(6) 0.0323(8) 0.0018(5) 0.0085(6) -0.0047(5) C8 0.0330(7) 0.0255(6) 0.0249(7) 0.0031(5) 0.0030(5) 0.0052(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 O1 C4 1.3406(13) . ? O1 C3 1.4522(13) . ? O3 C4 1.3461(14) . ? O3 C5 1.4185(13) . ? O2 C4 1.1911(13) . ? C2 C1 1.1944(15) . ? C2 C3 1.4631(16) . ? C5 C6 1.3717(16) . ? C5 C10 1.3770(16) . ? C1 C1 1.380(2) 2_765 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C9 C8 1.3808(16) . ? C9 C10 1.3877(16) . ? C9 H9 0.9300 . ? C6 C7 1.3890(16) . ? C6 H6 0.9300 . ? C10 H10 0.9300 . ? C7 C8 1.3808(18) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? 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 O1 C3 113.77(9) . . ? C4 O3 C5 115.89(8) . . ? C1 C2 C3 178.59(13) . . ? O2 C4 O1 126.73(11) . . ? O2 C4 O3 126.76(11) . . ? O1 C4 O3 106.51(9) . . ? C6 C5 C10 122.28(11) . . ? C6 C5 O3 117.93(10) . . ? C10 C5 O3 119.68(10) . . ? C2 C1 C1 177.36(8) . 2_765 ? O1 C3 C2 111.08(9) . . ? O1 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? O1 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C8 C9 C10 120.09(11) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C6 C7 118.51(11) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C5 C10 C9 118.65(10) . . ? C5 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C8 C7 C6 120.29(11) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 120.18(11) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? 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 O1 C4 O2 -1.81(15) . . . . ? C3 O1 C4 O3 178.88(8) . . . . ? C5 O3 C4 O2 4.20(16) . . . . ? C5 O3 C4 O1 -176.49(8) . . . . ? C4 O3 C5 C6 -112.89(11) . . . . ? C4 O3 C5 C10 70.76(13) . . . . ? C4 O1 C3 C2 -75.32(11) . . . . ? C10 C5 C6 C7 -0.23(17) . . . . ? O3 C5 C6 C7 -176.48(10) . . . . ? C6 C5 C10 C9 -0.19(17) . . . . ? O3 C5 C10 C9 176.00(10) . . . . ? C8 C9 C10 C5 0.29(17) . . . . ? C5 C6 C7 C8 0.55(18) . . . . ? C10 C9 C8 C7 0.03(18) . . . . ? C6 C7 C8 C9 -0.46(19) . . . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 759062' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #TrackingRef '246trifphenol_5.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Jan 29 15:14:15 2013' _audit_creation_method 'PLATON
option' _audit_update_record ; ; #=============================================================================== data_aveb246tfp150k #TrackingRef '246trifphenol_5.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'hexa-2,4-diyne-1,6-diyl bis(2,4,6-trifluorophenylcarbonate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H8 F6 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 H8 F6 O6' _chemical_formula_iupac ? _chemical_formula_weight 458.26 _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 Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.2422(3) _cell_length_b 7.1560(4) _cell_length_c 13.2155(7) _cell_angle_alpha 93.426(4) _cell_angle_beta 98.645(4) _cell_angle_gamma 109.868(5) _cell_volume 457.66(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9493 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 230 _exptl_absorpt_coefficient_mu 0.161 _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 0.9532 _exptl_absorpt_correction_T_max 0.9684 #=============================================================================== # 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 9493 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _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 1614 # number of observed reflections (> n sig(I)) _reflns_number_gt 1454 _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^)+(0.0354P)^2^+0.1619P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1614 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.191 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.034 #=============================================================================== # 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 0.49204(18) 0.59217(14) 0.14538(7) 0.0252(2) Uani 1 1 d . . . O3 O 0.37861(19) 0.39009(15) 0.25854(7) 0.0289(2) Uani 1 1 d . . . F1 F 0.06428(18) 0.50106(12) 0.38261(7) 0.0370(2) Uani 1 1 d . . . F3 F 0.29178(18) -0.00496(13) 0.22302(6) 0.0371(2) Uani 1 1 d . . . F2 F -0.39410(18) -0.16715(13) 0.42595(7) 0.0442(3) Uani 1 1 d . . . C5 C 0.1792(3) 0.2505(2) 0.30071(10) 0.0235(3) Uani 1 1 d . . . C2 C 0.6736(3) 0.8264(2) 0.03497(10) 0.0252(3) Uani 1 1 d . . . C4 C 0.2766(3) 0.47261(19) 0.17963(10) 0.0219(3) Uani 1 1 d . . . O2 O 0.03961(19) 0.44189(15) 0.14882(8) 0.0322(3) Uani 1 1 d . . . C6 C 0.0229(3) 0.30538(19) 0.36375(10) 0.0252(3) Uani 1 1 d . . . C7 C -0.1702(3) 0.1685(2) 0.40723(11) 0.0277(3) Uani 1 1 d . . . H7 H -0.2741 0.2076 0.4496 0.033 Uiso 1 1 calc R . . C1 C 0.8798(3) 0.9361(2) 0.01254(10) 0.0253(3) Uani 1 1 d . . . C10 C 0.1378(3) 0.0497(2) 0.28325(10) 0.0256(3) Uani 1 1 d . . . C9 C -0.0521(3) -0.0941(2) 0.32436(11) 0.0286(3) Uani 1 1 d . . . H9 H -0.0777 -0.2291 0.3117 0.034 Uiso 1 1 calc R . . C8 C -0.2025(3) -0.0287(2) 0.38515(11) 0.0286(3) Uani 1 1 d . . . C3 C 0.4172(3) 0.6943(2) 0.06037(10) 0.0241(3) Uani 1 1 d . . . H3A H 0.3081 0.7711 0.0803 0.029 Uiso 1 1 calc R . . H3B H 0.3097 0.5980 0.0013 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0222(5) 0.0275(5) 0.0253(5) 0.0096(4) 0.0049(4) 0.0067(4) O3 0.0222(5) 0.0339(5) 0.0296(5) 0.0146(4) 0.0046(4) 0.0071(4) F1 0.0459(5) 0.0214(4) 0.0445(5) 0.0025(4) 0.0112(4) 0.0120(4) F3 0.0400(5) 0.0456(5) 0.0318(5) -0.0016(4) 0.0077(4) 0.0232(4) F2 0.0363(5) 0.0366(5) 0.0527(6) 0.0175(4) 0.0144(4) -0.0009(4) C5 0.0206(7) 0.0259(7) 0.0219(7) 0.0080(5) 0.0020(5) 0.0055(5) C2 0.0301(7) 0.0248(7) 0.0233(7) 0.0065(5) 0.0069(6) 0.0116(6) C4 0.0235(7) 0.0215(6) 0.0211(7) 0.0035(5) 0.0053(5) 0.0077(5) O2 0.0218(5) 0.0421(6) 0.0326(6) 0.0150(5) 0.0055(4) 0.0092(4) C6 0.0287(7) 0.0198(7) 0.0259(7) 0.0027(5) 0.0011(6) 0.0085(6) C7 0.0263(7) 0.0319(8) 0.0254(7) 0.0042(6) 0.0069(6) 0.0098(6) C1 0.0287(7) 0.0258(7) 0.0241(7) 0.0077(6) 0.0057(6) 0.0119(6) C10 0.0280(7) 0.0317(7) 0.0192(7) 0.0014(6) 0.0007(5) 0.0150(6) C9 0.0321(8) 0.0210(7) 0.0286(7) 0.0026(6) -0.0035(6) 0.0080(6) C8 0.0240(7) 0.0272(7) 0.0286(7) 0.0099(6) 0.0024(6) 0.0013(6) C3 0.0249(7) 0.0269(7) 0.0240(7) 0.0077(5) 0.0073(5) 0.0114(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.3249(16) . ? O1 C3 1.4529(16) . ? O3 C4 1.3573(16) . ? O3 C5 1.3902(15) . ? F1 C6 1.3437(15) . ? F3 C10 1.3446(16) . ? F2 C8 1.3534(16) . ? C5 C10 1.3784(19) . ? C5 C6 1.380(2) . ? C2 C1 1.1917(19) . ? C2 C3 1.4573(18) . ? C4 O2 1.1872(16) . ? C6 C7 1.3720(19) . ? C7 C8 1.371(2) . ? C7 H7 0.9300 . ? C1 C1 1.383(3) 2_775 ? C10 C9 1.371(2) . ? C9 C8 1.372(2) . ? C9 H9 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? 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 O1 C3 113.43(10) . . ? C4 O3 C5 114.57(10) . . ? C10 C5 C6 117.37(12) . . ? C10 C5 O3 120.25(12) . . ? C6 C5 O3 122.35(12) . . ? C1 C2 C3 178.46(14) . . ? O2 C4 O1 127.69(12) . . ? O2 C4 O3 125.76(12) . . ? O1 C4 O3 106.55(10) . . ? F1 C6 C7 119.52(12) . . ? F1 C6 C5 117.92(12) . . ? C7 C6 C5 122.56(13) . . ? C8 C7 C6 116.71(13) . . ? C8 C7 H7 121.6 . . ? C6 C7 H7 121.6 . . ? C2 C1 C1 179.48(19) . 2_775 ? F3 C10 C9 119.42(13) . . ? F3 C10 C5 117.80(12) . . ? C9 C10 C5 122.79(13) . . ? C10 C9 C8 116.58(13) . . ? C10 C9 H9 121.7 . . ? C8 C9 H9 121.7 . . ? F2 C8 C7 117.94(13) . . ? F2 C8 C9 118.07(13) . . ? C7 C8 C9 123.99(13) . . ? O1 C3 C2 106.96(10) . . ? O1 C3 H3A 110.3 . . ? C2 C3 H3A 110.3 . . ? O1 C3 H3B 110.3 . . ? C2 C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? 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 107.91(14) . . . . ? C4 O3 C5 C6 -74.40(16) . . . . ? C3 O1 C4 O2 0.24(19) . . . . ? C3 O1 C4 O3 -179.55(10) . . . . ? C5 O3 C4 O2 3.55(19) . . . . ? C5 O3 C4 O1 -176.65(10) . . . . ? C10 C5 C6 F1 179.02(11) . . . . ? O3 C5 C6 F1 1.26(19) . . . . ? C10 C5 C6 C7 -0.9(2) . . . . ? O3 C5 C6 C7 -178.64(12) . . . . ? F1 C6 C7 C8 -179.92(12) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C6 C5 C10 F3 -179.14(11) . . . . ? O3 C5 C10 F3 -1.33(18) . . . . ? C6 C5 C10 C9 1.0(2) . . . . ? O3 C5 C10 C9 178.77(11) . . . . ? F3 C10 C9 C8 179.97(11) . . . . ? C5 C10 C9 C8 -0.1(2) . . . . ? C6 C7 C8 F2 -179.16(12) . . . . ? C6 C7 C8 C9 0.9(2) . . . . ? C10 C9 C8 F2 179.23(12) . . . . ? C10 C9 C8 C7 -0.9(2) . . . . ? C4 O1 C3 C2 177.20(10) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 922272' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #TrackingRef '246trifphenol_5.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Jan 29 15:14:15 2013' _audit_creation_method 'PLATON
option' _audit_update_record ; ; #===END # Attachment 'mfphenol_3.cif' # CIF-file generated for avebmfp_150 in P2(1)/n #============================================================================== data_avebmfp_150 #TrackingRef 'mfphenol_3.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'hexa-2,4-diyne-1,6-diyl bis(3-fluorophenylcarbonate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 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 'C20 H12 F2 O6' _chemical_formula_iupac ? _chemical_formula_weight 386.30 _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 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 20.8305(12) _cell_length_b 3.9051(3) _cell_length_c 22.4954(12) _cell_angle_alpha 90 _cell_angle_beta 110.433(7) _cell_angle_gamma 90 _cell_volume 1714.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 18137 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.125 _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 0.9517 _exptl_absorpt_correction_T_max 0.9876 #=============================================================================== # 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 18137 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3031 # number of observed reflections (> n sig(I)) _reflns_number_gt 2552 _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^)+(0.0538P)^2^+0.3818P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3031 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.167 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.043 #=============================================================================== # 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 0.85464(5) 0.9941(3) 1.18908(5) 0.0262(3) Uani 1 1 d . . . O1 O 0.88027(6) 0.7534(3) 0.84995(5) 0.0287(3) Uani 1 1 d . . . O3' O 0.75005(5) 0.9075(3) 1.17781(5) 0.0290(3) Uani 1 1 d . . . F1 F 0.89910(6) 1.0826(3) 0.57163(5) 0.0451(3) Uani 1 1 d . . . O2 O 0.92900(6) 0.5334(4) 0.78336(5) 0.0377(3) Uani 1 1 d . . . F1' F 0.53525(5) 1.1293(3) 1.19380(5) 0.0487(3) Uani 1 1 d . . . C1 C 0.91878(8) 0.7912(4) 1.00880(7) 0.0253(4) Uani 1 1 d . . . C2 C 0.92291(8) 0.6892(4) 0.96015(7) 0.0255(4) Uani 1 1 d . . . O2' O 0.77396(6) 1.2548(3) 1.10708(5) 0.0333(3) Uani 1 1 d . . . C4' C 0.79045(8) 1.0734(4) 1.15222(7) 0.0244(4) Uani 1 1 d . . . O3 O 0.83472(6) 0.8721(3) 0.75141(5) 0.0341(3) Uani 1 1 d . . . C4 C 0.88617(8) 0.6995(4) 0.79335(7) 0.0238(4) Uani 1 1 d . . . C1' C 0.91473(8) 0.9124(4) 1.06484(7) 0.0252(4) Uani 1 1 d . . . C2' C 0.91204(8) 1.0240(4) 1.11329(7) 0.0256(4) Uani 1 1 d . . . C3 C 0.92891(9) 0.5665(4) 0.90133(7) 0.0280(4) Uani 1 1 d . . . H3A H 0.9750 0.6042 0.9016 0.034 Uiso 1 1 calc R . . H3B H 0.9192 0.3231 0.8965 0.034 Uiso 1 1 calc R . . C6 C 0.87152(8) 0.9727(4) 0.66206(7) 0.0277(4) Uani 1 1 d . . . H6 H 0.9123 1.0725 0.6879 0.033 Uiso 1 1 calc R . . C10' C 0.64720(9) 0.8051(5) 1.08636(7) 0.0294(4) Uani 1 1 d . . . H10' H 0.6730 0.7308 1.0624 0.035 Uiso 1 1 calc R . . C3' C 0.90770(8) 1.1610(4) 1.17215(7) 0.0271(4) Uani 1 1 d . . . H3'1 H 0.9514 1.1300 1.2061 0.032 Uiso 1 1 calc R . . H3'2 H 0.8983 1.4047 1.1673 0.032 Uiso 1 1 calc R . . C5 C 0.82482(8) 0.8396(4) 0.68642(7) 0.0266(4) Uani 1 1 d . . . C6' C 0.64233(8) 1.0373(4) 1.18430(7) 0.0269(4) Uani 1 1 d . . . H6' H 0.6644 1.1190 1.2252 0.032 Uiso 1 1 calc R . . C5' C 0.67828(8) 0.9249(4) 1.14732(7) 0.0252(4) Uani 1 1 d . . . C8' C 0.53804(9) 0.9065(5) 1.09764(8) 0.0312(4) Uani 1 1 d . . . H8' H 0.4904 0.8996 1.0812 0.037 Uiso 1 1 calc R . . C7' C 0.57228(9) 1.0236(5) 1.15806(8) 0.0303(4) Uani 1 1 d . . . C7 C 0.85459(9) 0.9501(5) 0.59735(8) 0.0298(4) Uani 1 1 d . . . C10 C 0.76422(9) 0.6941(5) 0.64902(8) 0.0344(4) Uani 1 1 d . . . H10 H 0.7334 0.6075 0.6668 0.041 Uiso 1 1 calc R . . C9' C 0.57654(9) 0.7992(5) 1.06199(8) 0.0319(4) Uani 1 1 d . . . H9' H 0.5544 0.7216 1.0208 0.038 Uiso 1 1 calc R . . C8 C 0.79528(9) 0.8076(5) 0.55772(8) 0.0359(4) Uani 1 1 d . . . H8 H 0.7858 0.7976 0.5142 0.043 Uiso 1 1 calc R . . C9 C 0.74993(9) 0.6791(5) 0.58427(9) 0.0405(5) Uani 1 1 d . . . H9 H 0.7091 0.5809 0.5583 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1' 0.0229(6) 0.0351(7) 0.0204(5) 0.0032(5) 0.0074(5) 0.0019(5) O1 0.0314(6) 0.0351(7) 0.0205(6) 0.0021(5) 0.0102(5) 0.0084(5) O3' 0.0220(6) 0.0428(8) 0.0210(6) 0.0062(5) 0.0060(5) 0.0022(5) F1 0.0442(6) 0.0618(8) 0.0361(6) 0.0077(5) 0.0225(5) -0.0029(6) O2 0.0365(7) 0.0507(9) 0.0250(6) -0.0019(6) 0.0097(5) 0.0152(6) F1' 0.0342(6) 0.0801(9) 0.0367(6) -0.0058(6) 0.0185(5) 0.0076(6) C1 0.0235(8) 0.0277(9) 0.0233(8) 0.0039(7) 0.0066(6) 0.0028(7) C2 0.0266(8) 0.0247(9) 0.0247(8) 0.0021(7) 0.0085(7) 0.0005(7) O2' 0.0348(6) 0.0358(7) 0.0280(6) 0.0106(6) 0.0091(5) 0.0073(6) C4' 0.0262(8) 0.0257(9) 0.0208(8) -0.0022(7) 0.0074(7) 0.0033(7) O3 0.0331(6) 0.0482(8) 0.0218(6) 0.0053(5) 0.0106(5) 0.0130(6) C4 0.0243(8) 0.0249(9) 0.0223(8) -0.0015(7) 0.0084(6) -0.0029(7) C1' 0.0251(8) 0.0264(9) 0.0240(8) 0.0034(7) 0.0084(7) 0.0021(7) C2' 0.0248(8) 0.0266(9) 0.0253(8) 0.0039(7) 0.0085(7) 0.0020(7) C3 0.0340(9) 0.0268(9) 0.0226(8) 0.0015(7) 0.0089(7) 0.0059(8) C6 0.0237(8) 0.0319(10) 0.0252(8) -0.0009(7) 0.0058(7) 0.0002(7) C10' 0.0320(9) 0.0321(10) 0.0235(8) -0.0015(7) 0.0090(7) 0.0056(8) C3' 0.0280(8) 0.0295(10) 0.0252(8) -0.0020(7) 0.0111(7) -0.0031(7) C5 0.0281(8) 0.0298(9) 0.0211(8) 0.0015(7) 0.0077(7) 0.0043(7) C6' 0.0284(9) 0.0319(10) 0.0191(8) -0.0019(7) 0.0066(7) -0.0002(7) C5' 0.0230(8) 0.0286(9) 0.0219(8) 0.0038(7) 0.0054(6) 0.0021(7) C8' 0.0255(8) 0.0340(10) 0.0304(9) 0.0040(8) 0.0050(7) -0.0003(8) C7' 0.0304(9) 0.0363(10) 0.0280(9) 0.0024(7) 0.0149(7) 0.0041(8) C7 0.0309(9) 0.0341(10) 0.0269(8) 0.0044(7) 0.0131(7) 0.0027(8) C10 0.0270(9) 0.0362(11) 0.0396(10) 0.0053(8) 0.0109(8) -0.0014(8) C9' 0.0337(9) 0.0327(10) 0.0231(8) -0.0025(7) 0.0021(7) 0.0009(8) C8 0.0404(10) 0.0382(11) 0.0231(8) -0.0008(8) 0.0037(7) 0.0020(9) C9 0.0332(10) 0.0397(12) 0.0385(10) -0.0038(9) -0.0001(8) -0.0064(9) _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' C4' 1.3406(19) . ? O1' C3' 1.4441(19) . ? O1 C4 1.3376(18) . ? O1 C3 1.4414(19) . ? O3' C4' 1.341(2) . ? O3' C5' 1.4120(19) . ? F1 C7 1.3552(19) . ? O2 C4 1.1862(19) . ? F1' C7' 1.3583(19) . ? C1 C2 1.196(2) . ? C1 C1' 1.376(2) . ? C2 C3 1.453(2) . ? O2' C4' 1.1861(19) . ? O3 C4 1.337(2) . ? O3 C5 1.4091(18) . ? C1' C2' 1.193(2) . ? C2' C3' 1.460(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C6 C5 1.374(2) . ? C6 C7 1.376(2) . ? C6 H6 0.9300 . ? C10' C5' 1.378(2) . ? C10' C9' 1.380(2) . ? C10' H10' 0.9300 . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C5 C10 1.372(2) . ? C6' C7' 1.371(2) . ? C6' C5' 1.371(2) . ? C6' H6' 0.9300 . ? C8' C7' 1.374(2) . ? C8' C9' 1.382(2) . ? C8' H8' 0.9300 . ? C7 C8 1.364(3) . ? C10 C9 1.382(2) . ? C10 H10 0.9300 . ? C9' H9' 0.9300 . ? C8 C9 1.376(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? 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' O1' C3' 115.00(12) . . ? C4 O1 C3 114.29(12) . . ? C4' O3' C5' 119.02(12) . . ? C2 C1 C1' 179.13(19) . . ? C1 C2 C3 179.23(17) . . ? O2' C4' O1' 126.56(15) . . ? O2' C4' O3' 128.20(15) . . ? O1' C4' O3' 105.24(13) . . ? C4 O3 C5 118.53(12) . . ? O2 C4 O3 127.78(14) . . ? O2 C4 O1 126.25(15) . . ? O3 C4 O1 105.97(13) . . ? C2' C1' C1 178.49(19) . . ? C1' C2' C3' 179.20(17) . . ? O1 C3 C2 107.68(13) . . ? O1 C3 H3A 110.2 . . ? C2 C3 H3A 110.2 . . ? O1 C3 H3B 110.2 . . ? C2 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C5 C6 C7 116.23(15) . . ? C5 C6 H6 121.9 . . ? C7 C6 H6 121.9 . . ? C5' C10' C9' 117.80(15) . . ? C5' C10' H10' 121.1 . . ? C9' C10' H10' 121.1 . . ? O1' C3' C2' 111.68(13) . . ? O1' C3' H3'1 109.3 . . ? C2' C3' H3'1 109.3 . . ? O1' C3' H3'2 109.3 . . ? C2' C3' H3'2 109.3 . . ? H3'1 C3' H3'2 107.9 . . ? C10 C5 C6 122.67(15) . . ? C10 C5 O3 116.33(15) . . ? C6 C5 O3 120.80(14) . . ? C7' C6' C5' 116.81(15) . . ? C7' C6' H6' 121.6 . . ? C5' C6' H6' 121.6 . . ? C6' C5' C10' 123.10(15) . . ? C6' C5' O3' 115.50(13) . . ? C10' C5' O3' 121.13(14) . . ? C7' C8' C9' 117.96(15) . . ? C7' C8' H8' 121.0 . . ? C9' C8' H8' 121.0 . . ? F1' C7' C6' 118.20(15) . . ? F1' C7' C8' 118.73(15) . . ? C6' C7' C8' 123.07(15) . . ? F1 C7 C8 118.37(15) . . ? F1 C7 C6 117.81(15) . . ? C8 C7 C6 123.82(16) . . ? C5 C10 C9 118.50(16) . . ? C5 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10' C9' C8' 121.25(16) . . ? C10' C9' H9' 119.4 . . ? C8' C9' H9' 119.4 . . ? C7 C8 C9 117.86(16) . . ? C7 C8 H8 121.1 . . ? C9 C8 H8 121.1 . . ? C8 C9 C10 120.92(17) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? 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' O1' C4' O2' 2.5(2) . . . . ? C3' O1' C4' O3' -176.93(12) . . . . ? C5' O3' C4' O2' 4.0(3) . . . . ? C5' O3' C4' O1' -176.57(13) . . . . ? C5 O3 C4 O2 5.5(3) . . . . ? C5 O3 C4 O1 -175.01(13) . . . . ? C3 O1 C4 O2 -4.6(2) . . . . ? C3 O1 C4 O3 175.84(13) . . . . ? C4 O1 C3 C2 171.67(14) . . . . ? C4' O1' C3' C2' -71.41(18) . . . . ? C7 C6 C5 C10 -0.6(3) . . . . ? C7 C6 C5 O3 -175.26(15) . . . . ? C4 O3 C5 C10 116.51(18) . . . . ? C4 O3 C5 C6 -68.5(2) . . . . ? C7' C6' C5' C10' 0.6(3) . . . . ? C7' C6' C5' O3' -173.50(15) . . . . ? C9' C10' C5' C6' -0.1(3) . . . . ? C9' C10' C5' O3' 173.69(15) . . . . ? C4' O3' C5' C6' -125.15(16) . . . . ? C4' O3' C5' C10' 60.7(2) . . . . ? C5' C6' C7' F1' 179.21(15) . . . . ? C5' C6' C7' C8' -0.4(3) . . . . ? C9' C8' C7' F1' -179.86(16) . . . . ? C9' C8' C7' C6' -0.2(3) . . . . ? C5 C6 C7 F1 179.21(15) . . . . ? C5 C6 C7 C8 0.4(3) . . . . ? C6 C5 C10 C9 0.5(3) . . . . ? O3 C5 C10 C9 175.39(16) . . . . ? C5' C10' C9' C8' -0.6(3) . . . . ? C7' C8' C9' C10' 0.8(3) . . . . ? F1 C7 C8 C9 -178.90(17) . . . . ? C6 C7 C8 C9 -0.1(3) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C5 C10 C9 C8 -0.1(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 922273' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #TrackingRef '246trifphenol_5.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Jan 29 15:14:15 2013' _audit_creation_method 'PLATON
option' _audit_update_record ; ; #===END # Attachment 'ofphenol_2.cif' # CIF-file generated for avebofp150k in Pccn #============================================================================== data_avebofp150k #TrackingRef 'ofphenol_2.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'hexa-2,4-diyne-1,6-diyl bis(2-fluorophenylcarbonate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 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 'C20 H12 F2 O6' _chemical_formula_iupac ? _chemical_formula_weight 386.30 _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 '-P 2ab 2ac' _symmetry_space_group_name_H-M 'P c c n' _symmetry_Int_Tables_number 56 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2-y,z 3 1/2+x,-y,1/2-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,1/2+y,-z 7 1/2-x,y,1/2+z 8 x,1/2-y,1/2+z _cell_length_a 22.665(5) _cell_length_b 9.956(5) _cell_length_c 7.442(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1679.3(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9474 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.128 _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 0.9507 _exptl_absorpt_correction_T_max 0.9749 #=============================================================================== # 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 9474 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _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 1480 # number of observed reflections (> n sig(I)) _reflns_number_gt 1172 _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^)+(0.0507P)^2^+0.0496P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1480 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.188 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.043 #=============================================================================== # 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 C3 C 0.19458(8) -0.06065(18) 1.0815(2) 0.0279(4) Uani 1 1 d . . . H3A H 0.2191 -0.1226 1.1490 0.034 Uiso 1 1 calc R . . H3B H 0.1552 -0.0627 1.1328 0.034 Uiso 1 1 calc R . . F1 F 0.07030(5) -0.25122(10) 0.48232(14) 0.0368(3) Uani 1 1 d . . . C8 C 0.03694(8) 0.05715(19) 0.2482(2) 0.0285(4) Uani 1 1 d . . . H8 H 0.0113 0.0896 0.1608 0.034 Uiso 1 1 calc R . . C7 C 0.03360(8) -0.07560(19) 0.3015(2) 0.0278(4) Uani 1 1 d . . . H7 H 0.0058 -0.1330 0.2512 0.033 Uiso 1 1 calc R . . O1 O 0.19194(5) -0.10340(12) 0.89478(15) 0.0262(3) Uani 1 1 d . . . O2 O 0.11437(5) 0.03550(13) 0.85426(16) 0.0298(4) Uani 1 1 d . . . O3 O 0.15287(5) -0.09285(12) 0.63193(15) 0.0281(3) Uani 1 1 d . . . C5 C 0.11319(7) -0.03724(17) 0.5074(2) 0.0227(4) Uani 1 1 d . . . C9 C 0.07822(8) 0.14162(18) 0.3241(2) 0.0288(4) Uani 1 1 d . . . H9 H 0.0803 0.2308 0.2875 0.035 Uiso 1 1 calc R . . C6 C 0.07216(7) -0.12110(17) 0.4301(2) 0.0237(4) Uani 1 1 d . . . C2 C 0.21868(7) 0.07495(19) 1.0970(2) 0.0266(4) Uani 1 1 d . . . C4 C 0.14910(8) -0.04436(17) 0.8013(2) 0.0234(4) Uani 1 1 d . . . C10 C 0.11652(7) 0.09434(18) 0.4545(2) 0.0273(4) Uani 1 1 d . . . H10 H 0.1443 0.1515 0.5058 0.033 Uiso 1 1 calc R . . C1 C 0.23840(8) 0.18588(18) 1.1051(2) 0.0261(4) 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 C3 0.0322(11) 0.0271(10) 0.0244(9) 0.0025(8) -0.0027(8) -0.0016(8) F1 0.0459(7) 0.0199(6) 0.0445(7) 0.0034(5) -0.0023(5) -0.0047(4) C8 0.0270(10) 0.0325(11) 0.0259(10) 0.0004(8) -0.0019(7) 0.0050(8) C7 0.0254(10) 0.0306(11) 0.0274(10) -0.0058(9) -0.0012(8) -0.0032(8) O1 0.0268(7) 0.0276(7) 0.0241(6) -0.0001(6) -0.0030(5) 0.0034(5) O2 0.0328(8) 0.0282(7) 0.0285(7) -0.0022(6) -0.0003(5) 0.0089(6) O3 0.0315(7) 0.0283(7) 0.0246(6) -0.0034(5) -0.0044(5) 0.0072(6) C5 0.0236(10) 0.0240(10) 0.0205(9) -0.0020(8) 0.0002(7) 0.0034(7) C9 0.0313(11) 0.0207(10) 0.0344(10) 0.0031(8) 0.0017(8) 0.0011(8) C6 0.0261(10) 0.0193(9) 0.0258(9) -0.0006(8) 0.0048(7) -0.0010(7) C2 0.0232(10) 0.0339(11) 0.0228(9) 0.0016(8) -0.0023(7) 0.0016(8) C4 0.0242(10) 0.0203(9) 0.0259(9) 0.0017(8) -0.0004(7) -0.0036(7) C10 0.0261(10) 0.0256(10) 0.0303(10) -0.0043(8) -0.0014(7) -0.0036(8) C1 0.0226(9) 0.0301(11) 0.0256(9) 0.0013(8) 0.0004(7) 0.0004(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 C3 O1 1.454(2) . ? C3 C2 1.461(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? F1 C6 1.353(2) . ? C8 C9 1.379(3) . ? C8 C7 1.382(3) . ? C8 H8 0.9300 . ? C7 C6 1.373(2) . ? C7 H7 0.9300 . ? O1 C4 1.331(2) . ? O2 C4 1.186(2) . ? O3 C4 1.352(2) . ? O3 C5 1.405(2) . ? C5 C10 1.370(3) . ? C5 C6 1.376(2) . ? C9 C10 1.385(3) . ? C9 H9 0.9300 . ? C2 C1 1.193(3) . ? C10 H10 0.9300 . ? C1 C1 1.381(4) 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 O1 C3 C2 111.19(14) . . ? O1 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? O1 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C9 C8 C7 120.19(17) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C6 C7 C8 118.74(17) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C4 O1 C3 113.58(13) . . ? C4 O3 C5 115.70(13) . . ? C10 C5 C6 119.83(16) . . ? C10 C5 O3 122.08(15) . . ? C6 C5 O3 117.98(15) . . ? C8 C9 C10 120.34(17) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? F1 C6 C7 119.75(15) . . ? F1 C6 C5 118.82(15) . . ? C7 C6 C5 121.43(17) . . ? C1 C2 C3 178.35(19) . . ? O2 C4 O1 127.32(16) . . ? O2 C4 O3 126.23(16) . . ? O1 C4 O3 106.46(14) . . ? C5 C10 C9 119.47(16) . . ? C5 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C2 C1 C1 177.09(13) . 2 ? 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 C9 C8 C7 C6 -0.3(3) . . . . ? C2 C3 O1 C4 -73.79(18) . . . . ? C4 O3 C5 C10 66.8(2) . . . . ? C4 O3 C5 C6 -116.90(17) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C7 C6 F1 -178.96(15) . . . . ? C8 C7 C6 C5 0.7(3) . . . . ? C10 C5 C6 F1 178.94(14) . . . . ? O3 C5 C6 F1 2.6(2) . . . . ? C10 C5 C6 C7 -0.8(3) . . . . ? O3 C5 C6 C7 -177.12(14) . . . . ? C3 O1 C4 O2 -0.5(2) . . . . ? C3 O1 C4 O3 179.27(13) . . . . ? C5 O3 C4 O2 3.1(2) . . . . ? C5 O3 C4 O1 -176.59(13) . . . . ? C6 C5 C10 C9 0.3(3) . . . . ? O3 C5 C10 C9 176.51(14) . . . . ? C8 C9 C10 C5 0.1(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 922274' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #TrackingRef '246trifphenol_5.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Jan 29 15:14:15 2013' _audit_creation_method 'PLATON
option' _audit_update_record ; ; #===END # Attachment 'pfphenol_4.cif' # CIF-file generated for vebpf_k150 in Pccn #============================================================================== #=============================================================================== data_vebpf_k150 #TrackingRef 'pfphenol_4.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; hexa-2,4-diyne-1,6-diyl bis(4-fluorophenylcarbonate)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 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 'C20 H12 F2 O6' _chemical_formula_iupac ? _chemical_formula_weight 386.30 _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 '-P 2ab 2ac' _symmetry_space_group_name_H-M 'P c c n' _symmetry_Int_Tables_number 56 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2-y,z 3 1/2+x,-y,1/2-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,1/2+y,-z 7 1/2-x,y,1/2+z 8 x,1/2-y,1/2+z _cell_length_a 9.6359(9) _cell_length_b 23.748(2) _cell_length_c 7.2680(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1663.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 6892 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.129 _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 0.9503 _exptl_absorpt_correction_T_max 0.9747 #=============================================================================== # 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 6892 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1478 # number of observed reflections (> n sig(I)) _reflns_number_gt 1160 _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^)+(0.0621P)^2^+0.3673P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1478 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.238 _refine_diff_density_min -0.210 _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 O3 O 0.60855(13) 0.34810(5) 0.14882(17) 0.0263(3) Uani 1 1 d . . . O1 O 0.61914(13) 0.30738(5) 0.41334(16) 0.0244(3) Uani 1 1 d . . . O2 O 0.47445(14) 0.38168(6) 0.38138(17) 0.0317(4) Uani 1 1 d . . . C1 C 0.31644(19) 0.26070(7) 0.6217(2) 0.0219(4) Uani 1 1 d . . . C10 C 0.63387(18) 0.42558(8) -0.0563(2) 0.0218(4) Uani 1 1 d . . . H10 H 0.7265 0.4282 -0.0214 0.026 Uiso 1 1 calc R . . C2 C 0.4316(2) 0.27933(7) 0.6155(2) 0.0224(4) Uani 1 1 d . . . C4 C 0.55794(18) 0.34894(7) 0.3233(3) 0.0212(4) Uani 1 1 d . . . C3 C 0.57304(19) 0.30222(8) 0.6037(2) 0.0242(4) Uani 1 1 d . . . H3A H 0.5756 0.3390 0.6619 0.029 Uiso 1 1 calc R . . H3B H 0.6362 0.2777 0.6699 0.029 Uiso 1 1 calc R . . C7 C 0.35492(19) 0.41738(8) -0.1572(2) 0.0233(4) Uani 1 1 d . . . H7 H 0.2618 0.4153 -0.1902 0.028 Uiso 1 1 calc R . . C8 C 0.4417(2) 0.45612(8) -0.2370(2) 0.0250(5) Uani 1 1 d . . . C9 C 0.5792(2) 0.46161(8) -0.1903(3) 0.0263(5) Uani 1 1 d . . . H9 H 0.6347 0.4887 -0.2464 0.032 Uiso 1 1 calc R . . C6 C 0.41040(19) 0.38142(8) -0.0254(3) 0.0256(4) Uani 1 1 d . . . H6 H 0.3549 0.3542 0.0300 0.031 Uiso 1 1 calc R . . C5 C 0.54811(19) 0.38638(8) 0.0225(2) 0.0223(4) Uani 1 1 d . . . F1 F 0.38767(12) 0.49139(5) -0.36589(16) 0.0371(4) 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 O3 0.0272(7) 0.0307(7) 0.0209(7) 0.0036(6) 0.0035(5) 0.0056(6) O1 0.0221(7) 0.0308(8) 0.0202(7) 0.0010(6) 0.0018(5) 0.0004(5) O2 0.0361(8) 0.0335(8) 0.0256(8) -0.0010(6) 0.0033(6) 0.0096(6) C1 0.0256(10) 0.0216(9) 0.0186(9) 0.0001(8) -0.0006(7) 0.0016(8) C10 0.0171(9) 0.0267(10) 0.0218(10) -0.0040(8) 0.0012(8) -0.0008(7) C2 0.0281(10) 0.0219(9) 0.0174(9) 0.0020(8) -0.0014(8) 0.0009(8) C4 0.0189(9) 0.0229(10) 0.0216(10) -0.0034(8) 0.0018(8) -0.0026(8) C3 0.0233(10) 0.0303(10) 0.0191(10) 0.0024(8) -0.0011(8) -0.0026(8) C7 0.0190(9) 0.0286(10) 0.0223(10) -0.0023(8) -0.0017(8) -0.0011(8) C8 0.0306(11) 0.0263(10) 0.0182(9) 0.0005(8) 0.0002(8) 0.0058(8) C9 0.0279(10) 0.0249(10) 0.0262(10) -0.0004(8) 0.0069(8) -0.0043(8) C6 0.0272(10) 0.0251(10) 0.0244(10) 0.0001(8) 0.0055(8) -0.0042(8) C5 0.0277(10) 0.0230(9) 0.0162(9) -0.0008(8) 0.0011(8) 0.0031(8) F1 0.0341(7) 0.0416(7) 0.0354(7) 0.0138(6) 0.0002(5) 0.0059(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 O3 C4 1.359(2) . ? O3 C5 1.417(2) . ? O1 C4 1.323(2) . ? O1 C3 1.458(2) . ? O2 C4 1.196(2) . ? C1 C2 1.196(3) . ? C1 C1 1.378(4) 2 ? C10 C5 1.370(3) . ? C10 C9 1.399(3) . ? C10 H10 0.9300 . ? C2 C3 1.470(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C7 C8 1.372(3) . ? C7 C6 1.390(3) . ? C7 H7 0.9300 . ? C8 F1 1.361(2) . ? C8 C9 1.374(3) . ? C9 H9 0.9300 . ? C6 C5 1.377(3) . ? C6 H6 0.9300 . ? 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 116.61(14) . . ? C4 O1 C3 113.34(14) . . ? C2 C1 C1 177.83(12) . 2 ? C5 C10 C9 118.63(17) . . ? C5 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C1 C2 C3 178.83(18) . . ? O2 C4 O1 127.63(17) . . ? O2 C4 O3 125.48(17) . . ? O1 C4 O3 106.90(15) . . ? O1 C3 C2 111.64(14) . . ? O1 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? O1 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C8 C7 C6 117.94(17) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? F1 C8 C7 118.05(17) . . ? F1 C8 C9 118.76(17) . . ? C7 C8 C9 123.18(18) . . ? C8 C9 C10 118.49(17) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C5 C6 C7 119.49(17) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C10 C5 C6 122.27(17) . . ? C10 C5 O3 117.29(16) . . ? C6 C5 O3 120.33(16) . . ? 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 O1 C4 O2 1.4(3) . . . . ? C3 O1 C4 O3 -178.93(14) . . . . ? C5 O3 C4 O2 -5.6(3) . . . . ? C5 O3 C4 O1 174.78(14) . . . . ? C4 O1 C3 C2 72.63(19) . . . . ? C6 C7 C8 F1 -179.96(16) . . . . ? C6 C7 C8 C9 -1.3(3) . . . . ? F1 C8 C9 C10 179.38(16) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C5 C10 C9 C8 0.0(3) . . . . ? C8 C7 C6 C5 1.1(3) . . . . ? C9 C10 C5 C6 -0.2(3) . . . . ? C9 C10 C5 O3 175.98(16) . . . . ? C7 C6 C5 C10 -0.4(3) . . . . ? C7 C6 C5 O3 -176.45(15) . . . . ? C4 O3 C5 C10 119.47(17) . . . . ? C4 O3 C5 C6 -64.3(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 922275'