# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_red _database_code_depnum_ccdc_archive 'CCDC 881258' #TrackingRef '11177_web_deposit_cif_file_0_RiteshDubey_1336563816.24DFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 2,4-difluorobenzoic acid ; _chemical_name_common '2,4-difluorobenzoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 F2 O2' # 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 'C7 H3 F2 O2' _chemical_formula_iupac ? _chemical_formula_weight 157.09 _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 3.6912(2) _cell_length_b 6.4038(3) _cell_length_c 26.3062(15) _cell_angle_alpha 90 _cell_angle_beta 92.908(5) _cell_angle_gamma 90 _cell_volume 621.02(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1799 _cell_measurement_theta_min 2.3212 _cell_measurement_theta_max 29.0869 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.161 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9175 _exptl_absorpt_correction_T_max 0.9826 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Mova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Eos, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0839 # number of measured reflections (redundant set) _diffrn_reflns_number 3872 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1265 _reflns_number_gt 1147 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 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^)+(0.0349P)^2^+0.6516P] 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 1265 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_restrained_S_all 1.184 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.223 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.058 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F1 F Uani 1.0547(4) 0.0801(2) 0.16263(5) 0.918 0.0228(4) . . F2 F Uani 0.6023(4) 0.7201(2) 0.21545(5) 1.000 0.0315(4) . . O1 O Uani 0.7778(5) 0.2395(3) 0.01178(6) 1.000 0.0301(5) . . O2 O Uani 1.0773(4) 0.0121(3) 0.06286(6) 1.000 0.0264(5) . . C1 C Uani 0.8254(5) 0.3181(3) 0.09916(8) 1.000 0.0177(6) . . C2 C Uani 0.9040(5) 0.2660(3) 0.15005(8) 1.000 0.0194(6) . . C3 C Uani 0.8322(6) 0.3985(4) 0.18963(8) 1.000 0.0213(6) . . C4 C Uani 0.6778(5) 0.5885(4) 0.17689(8) 1.000 0.0214(6) . . C5 C Uani 0.5949(6) 0.6513(3) 0.12763(8) 1.000 0.0215(6) . . C6 C Uani 0.6701(5) 0.5142(3) 0.08897(8) 1.000 0.0198(6) . . C7 C Uani 0.9040(5) 0.1772(3) 0.05659(8) 1.000 0.0189(6) . . F1A F Uani 0.621(5) 0.568(3) 0.0515(7) 0.082 0.039(6) . . H3 H Uiso 0.880(6) 0.360(4) 0.2248(9) 1.000 0.017(6) . . H5 H Uiso 0.488(7) 0.794(4) 0.1205(9) 1.000 0.024(6) . . H1 H Uiso 0.832(12) 0.137(7) -0.0165(17) 1.000 0.108(16) . . 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 F1 0.0308(8) 0.0154(7) 0.0220(7) 0.0037(5) -0.0011(5) 0.0065(6) F2 0.0361(8) 0.0304(8) 0.0283(7) -0.0112(6) 0.0037(6) 0.0049(6) O1 0.0422(10) 0.0278(9) 0.0199(8) -0.0010(7) -0.0023(7) 0.0124(8) O2 0.0329(9) 0.0201(8) 0.0260(8) -0.0011(6) 0.0001(6) 0.0088(7) C1 0.0138(9) 0.0177(11) 0.0214(10) -0.0001(8) 0.0004(7) -0.0002(8) C2 0.0159(9) 0.0172(11) 0.0251(11) 0.0019(8) 0.0005(8) 0.0005(8) C3 0.0194(10) 0.0234(12) 0.0209(10) 0.0006(8) 0.0005(8) -0.0021(9) C4 0.0159(10) 0.0232(12) 0.0251(10) -0.0075(9) 0.0024(8) -0.0024(8) C5 0.0187(10) 0.0163(11) 0.0295(11) -0.0008(9) 0.0004(8) 0.0004(9) C6 0.0172(10) 0.0183(11) 0.0238(12) 0.0013(9) -0.0001(8) 0.0002(8) C7 0.0181(10) 0.0180(11) 0.0207(10) 0.0007(8) 0.0009(8) 0.0000(8) F1A 0.042(10) 0.047(12) 0.027(9) -0.005(8) 0.004(7) -0.001(9) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.348(2) . . yes F1A C6 1.051(19) . . yes F2 C4 1.359(3) . . yes O1 C7 1.308(3) . . yes O2 C7 1.242(3) . . yes O1 H1 1.02(4) . . no C1 C7 1.478(3) . . no C1 C2 1.396(3) . . no C1 C6 1.401(3) . . no C2 C3 1.379(3) . . no C3 C4 1.378(3) . . no C4 C5 1.376(3) . . no C5 C6 1.382(3) . . no C3 H3 0.97(2) . . no C5 H5 1.01(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 113(3) . . . no C2 C1 C6 117.45(18) . . . no C2 C1 C7 122.78(17) . . . no C6 C1 C7 119.76(18) . . . no F1 C2 C3 116.78(19) . . . yes C1 C2 C3 122.58(19) . . . no F1 C2 C1 120.64(18) . . . yes C2 C3 C4 116.91(19) . . . no F2 C4 C5 118.5(2) . . . yes C3 C4 C5 123.8(2) . . . no F2 C4 C3 117.66(19) . . . yes C4 C5 C6 117.63(19) . . . no F1A C6 C1 121.5(11) . . . yes F1A C6 C5 116.8(10) . . . yes C1 C6 C5 121.61(19) . . . no O1 C7 C1 114.96(17) . . . yes O2 C7 C1 122.57(19) . . . yes O1 C7 O2 122.47(19) . . . yes C2 C3 H3 122.3(15) . . . no C4 C3 H3 120.8(15) . . . no C4 C5 H5 120.4(14) . . . no C6 C5 H5 122.0(14) . . . no 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 C6 C1 C2 F1 -179.80(17) . . . . no C6 C1 C2 C3 0.5(3) . . . . no C7 C1 C2 F1 -0.7(3) . . . . no C7 C1 C2 C3 179.60(19) . . . . no C2 C1 C6 C5 -0.4(3) . . . . no C7 C1 C6 C5 -179.49(18) . . . . no C2 C1 C7 O1 172.81(18) . . . . no C2 C1 C7 O2 -7.3(3) . . . . no C6 C1 C7 O1 -8.1(3) . . . . no C6 C1 C7 O2 171.82(18) . . . . no F1 C2 C3 C4 -179.93(18) . . . . no C1 C2 C3 C4 -0.2(3) . . . . no C2 C3 C4 F2 179.42(18) . . . . no C2 C3 C4 C5 -0.3(3) . . . . no F2 C4 C5 C6 -179.29(18) . . . . no C3 C4 C5 C6 0.4(3) . . . . no C4 C5 C6 C1 -0.1(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F1 O2 2.666(2) . . no F1 C5 3.333(2) . 1_545 no F1A O1 2.492(19) . 3_665 no F1A O1 3.097(19) . 3_765 no F1A F1A 2.94(3) . 3_665 no F1A O1 2.432(19) . . no F2 C3 3.243(3) . 2_655 no F1 H5 2.71(3) . 1_645 no F1A H1 2.66(5) . 3_665 no F2 H3 2.57(2) . 2_755 no F2 H3 2.59(2) . 2_655 no O1 O2 2.616(2) . 3_755 no O1 F1A 2.432(19) . . no O1 F1A 3.097(19) . 3_765 no O1 F1A 2.492(19) . 3_665 no O2 C5 3.400(3) . 1_645 no O2 C7 3.242(2) . 1_655 no O2 F1 2.666(2) . . no O2 O1 2.616(2) . 3_755 no O2 C7 3.372(3) . 3_755 no O1 H1 2.81(4) . 3_755 no O2 H5 2.51(3) . 1_645 no O2 H1 1.60(4) . 3_755 no C1 C6 3.385(3) . 1_655 no C2 C4 3.566(3) . 1_655 no C3 F2 3.243(3) . 2_645 no C3 C4 3.383(3) . 1_655 no C4 C3 3.383(3) . 1_455 no C4 C2 3.566(3) . 1_455 no C5 F1 3.333(2) . 1_565 no C5 O2 3.400(3) . 1_465 no C6 C1 3.385(3) . 1_455 no C7 O2 3.372(3) . 3_755 no C7 O2 3.242(2) . 1_455 no C7 H1 2.49(4) . 3_755 no H1 O2 1.60(5) . 3_755 no H1 O1 2.81(4) . 3_755 no H1 H1 2.29(6) . 3_755 no H1 F1A 2.66(5) . 3_665 no H1 C7 2.49(4) . 3_755 no H3 F2 2.57(2) . 2_745 no H3 F2 2.59(2) . 2_645 no H5 O2 2.51(3) . 1_465 no H5 F1 2.71(3) . 1_465 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 1.02(4) 1.60(5) 2.616(2) 177(4) 3_755 yes C5 H5 O2 1.01(3) 2.51(3) 3.400(3) 146.5(19) 1_465 yes data_datam _database_code_depnum_ccdc_archive 'CCDC 881259' #TrackingRef '11178_web_deposit_cif_file_1_RiteshDubey_1336563816.25DFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H2 F2 O2' # 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 'C7 H2 F2 O2' _chemical_formula_iupac ? _chemical_formula_weight 156.09 _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 3.6960(5) _cell_length_b 14.768(2) _cell_length_c 11.9174(16) _cell_angle_alpha 90 _cell_angle_beta 93.025(7) _cell_angle_gamma 90 _cell_volume 649.58(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5816 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.6 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.154 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_T_max 0.985 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' # number of measured reflections (redundant set) _diffrn_reflns_number 6701 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1487 # number of observed reflections (> n sig(I)) _reflns_number_gt 1200 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0717P)^2^+0.0950P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1487 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.047 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F1 F Uani 0.3711(3) 0.76574(7) 0.35752(9) 0.810 0.0376(4) . . F2 F Uani -0.2211(3) 0.58775(9) -0.00370(9) 0.790 0.0482(4) . . O1 O Uani 0.2466(4) 0.48492(8) 0.36888(10) 1.000 0.0482(4) . . O2 O Uani 0.5051(3) 0.60440(7) 0.45263(9) 1.000 0.0390(4) . . C1 C Uani 0.1998(4) 0.62390(10) 0.27378(11) 1.000 0.0282(4) . . C2 C Uani 0.2278(4) 0.71776(11) 0.27090(12) 1.000 0.0319(4) . . C3 C Uani 0.1067(4) 0.76775(12) 0.17855(13) 1.000 0.0379(5) . . C4 C Uani -0.0460(4) 0.72388(12) 0.08528(13) 1.000 0.0376(5) . . C5 C Uani -0.0726(4) 0.63120(12) 0.08694(12) 1.000 0.0363(5) . . C6 C Uani 0.0441(4) 0.58026(11) 0.17863(12) 1.000 0.0330(4) . . C7 C Uani 0.3306(4) 0.57062(10) 0.37317(11) 1.000 0.0286(4) . . F2A F Uani 0.1794(18) 0.8466(4) 0.1907(6) 0.210 0.068(2) . . F1A F Uani -0.0210(18) 0.4937(4) 0.1709(4) 0.190 0.059(2) . . H4 H Uiso -0.131(5) 0.7571(13) 0.0181(15) 1.000 0.050(5) . . H1 H Uiso 0.358(7) 0.4518(18) 0.437(2) 1.000 0.091(8) . . 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 F1 0.0514(7) 0.0299(6) 0.0305(6) -0.0015(4) -0.0084(5) -0.0017(5) F2 0.0561(8) 0.0585(8) 0.0279(6) -0.0087(5) -0.0180(5) 0.0115(6) O1 0.0677(9) 0.0321(6) 0.0418(7) 0.0023(5) -0.0248(6) -0.0052(6) O2 0.0502(7) 0.0340(6) 0.0309(6) 0.0017(4) -0.0149(5) -0.0025(5) C1 0.0235(7) 0.0367(8) 0.0243(7) 0.0009(6) 0.0002(5) 0.0043(6) C2 0.0279(7) 0.0381(8) 0.0297(7) -0.0020(6) 0.0026(6) 0.0013(6) C3 0.0356(8) 0.0405(9) 0.0381(9) 0.0063(7) 0.0063(7) 0.0051(7) C4 0.0326(8) 0.0509(10) 0.0293(8) 0.0106(7) 0.0017(6) 0.0124(7) C5 0.0309(7) 0.0525(10) 0.0248(7) -0.0029(7) -0.0041(6) 0.0082(7) C6 0.0310(7) 0.0406(8) 0.0270(7) -0.0013(6) -0.0028(6) 0.0043(6) C7 0.0273(7) 0.0326(7) 0.0255(7) -0.0022(6) -0.0022(5) 0.0023(6) F2A 0.085(4) 0.042(3) 0.077(4) 0.028(3) 0.009(3) 0.019(3) F1A 0.080(4) 0.064(4) 0.030(3) -0.002(3) -0.020(3) 0.002(3) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.3381(18) . . yes F1A C6 1.303(6) . . yes F2 C5 1.3481(19) . . yes F2A C3 1.202(6) . . yes O1 C7 1.3035(19) . . yes O2 C7 1.2236(18) . . yes O1 H1 1.02(2) . . no C1 C7 1.482(2) . . no C1 C2 1.391(2) . . no C1 C6 1.401(2) . . no C2 C3 1.380(2) . . no C3 C4 1.381(2) . . no C4 C5 1.372(3) . . no C5 C6 1.377(2) . . no C4 H4 0.977(18) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 110.5(15) . . . no C2 C1 C6 117.80(13) . . . no C6 C1 C7 120.36(13) . . . no C2 C1 C7 121.84(13) . . . no F1 C2 C1 122.40(13) . . . yes C1 C2 C3 122.11(14) . . . no F1 C2 C3 115.50(14) . . . yes F2A C3 C2 111.2(4) . . . yes F2A C3 C4 129.1(4) . . . yes C2 C3 C4 119.50(16) . . . no C3 C4 C5 118.87(15) . . . no F2 C5 C4 119.31(14) . . . yes F2 C5 C6 118.23(15) . . . yes C4 C5 C6 122.45(14) . . . no F1A C6 C1 125.1(3) . . . yes F1A C6 C5 115.5(3) . . . yes C1 C6 C5 119.27(15) . . . no O1 C7 C1 114.66(12) . . . yes O2 C7 C1 122.59(13) . . . yes O1 C7 O2 122.75(13) . . . yes C3 C4 H4 121.6(11) . . . no C5 C4 H4 119.5(11) . . . no 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 C6 C1 C2 F1 179.78(13) . . . . no C6 C1 C2 C3 0.3(2) . . . . no C7 C1 C2 F1 -0.6(2) . . . . no C7 C1 C2 C3 179.96(15) . . . . no C2 C1 C6 C5 0.2(2) . . . . no C7 C1 C6 C5 -179.45(14) . . . . no C2 C1 C7 O1 172.06(14) . . . . no C2 C1 C7 O2 -8.3(2) . . . . no C6 C1 C7 O1 -8.3(2) . . . . no C6 C1 C7 O2 171.37(14) . . . . no F1 C2 C3 C4 -179.86(13) . . . . no C1 C2 C3 C4 -0.3(2) . . . . no C2 C3 C4 C5 -0.1(2) . . . . no C3 C4 C5 F2 -179.97(14) . . . . no C3 C4 C5 C6 0.7(2) . . . . no F2 C5 C6 C1 179.92(14) . . . . no C4 C5 C6 C1 -0.7(2) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F1 O2 2.6736(15) . . no F1 C4 3.1952(19) . 4_565 no F1A F2 2.578(5) . . no F1A O1 2.513(5) . . no F1A F2 2.531(5) . 3_565 no F2 F2 3.0629(18) . 3_565 no F2 C6 3.328(2) . 3_565 no F2 F1A 2.531(5) . 3_565 no F2 F1A 2.578(5) . . no F2A O1 3.056(7) . 2_655 no F2A O1 2.653(6) . 2_555 no F1 H4 2.606(18) . 4_665 no F1 H4 2.756(18) . 4_565 no F2A H1 2.82(3) . 2_655 no O1 F2A 2.653(6) . 2_545 no O1 F1A 2.513(5) . . no O1 F2A 3.056(7) . 2_645 no O1 O2 2.6270(17) . 3_666 no O2 C7 3.3506(18) . 3_666 no O2 O1 2.6270(17) . 3_666 no O2 F1 2.6736(15) . . no O2 C7 3.2802(19) . 1_655 no O2 C4 3.377(2) . 4_665 no O1 H1 2.83(2) . 3_666 no O2 H1 1.61(2) . 3_666 no O2 H4 2.548(19) . 4_665 no C1 C7 3.570(2) . 1_455 no C1 C6 3.437(2) . 1_655 no C1 C5 3.582(2) . 1_655 no C2 C3 3.562(2) . 1_655 no C2 C4 3.568(2) . 1_655 no C3 C2 3.562(2) . 1_455 no C3 C4 3.439(2) . 1_655 no C4 C3 3.439(2) . 1_455 no C4 C2 3.568(2) . 1_455 no C4 F1 3.1952(19) . 4_564 no C4 O2 3.377(2) . 4_464 no C5 C6 3.577(2) . 1_455 no C5 C1 3.582(2) . 1_455 no C6 C5 3.577(2) . 1_655 no C6 F2 3.328(2) . 3_565 no C6 C1 3.437(2) . 1_455 no C7 O2 3.3506(18) . 3_666 no C7 O2 3.2802(19) . 1_455 no C7 C1 3.570(2) . 1_655 no C7 H1 2.51(2) . 3_666 no H1 F2A 2.82(3) . 2_645 no H1 C7 2.51(2) . 3_666 no H1 O1 2.83(2) . 3_666 no H1 O2 1.61(2) . 3_666 no H1 H1 2.28(4) . 3_666 no H4 O2 2.548(19) . 4_464 no H4 F1 2.606(18) . 4_464 no H4 F1 2.756(18) . 4_564 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 1.02(2) 1.61(2) 2.6270(17) 174(2) 3_666 yes C4 H4 O2 0.977(18) 2.548(19) 3.377(2) 142.8(14) 4_464 yes data_datam3 _database_code_depnum_ccdc_archive 'CCDC 881260' #TrackingRef '11179_web_deposit_cif_file_2_RiteshDubey_1336563816.34DFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 F2 O2' # 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 'C7 H3 F2 O2' _chemical_formula_iupac ? _chemical_formula_weight 157.09 _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 C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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 5.5154(12) _cell_length_b 5.0528(11) _cell_length_c 23.144(5) _cell_angle_alpha 90 _cell_angle_beta 94.792(7) _cell_angle_gamma 90 _cell_volume 642.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4677 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.6 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.120 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.156 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.982 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' # number of measured reflections (redundant set) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_reflns_number 6090 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _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 1474 # number of observed reflections (> n sig(I)) _reflns_number_gt 1005 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0551P)^2^+0.2602P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1474 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.322 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.049 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1A F Uani 0.6845(3) 0.7708(3) 0.22838(7) 0.790 0.0524(6) d P . . F2 F Uani 0.2919(3) 1.0626(3) 0.21560(5) 1.000 0.0552(5) d . . . O1 O Uani 0.6445(3) 0.1422(3) 0.06177(6) 1.000 0.0391(5) d . . . O2 O Uani 0.2937(3) 0.2421(3) 0.01150(6) 1.000 0.0393(5) d . . . C1 C Uani 0.4071(4) 0.4852(4) 0.09699(8) 1.000 0.0290(6) d . . . C2 C Uani 0.5776(4) 0.5252(4) 0.14412(8) 1.000 0.0341(6) d . . . C3 C Uani 0.5336(5) 0.7213(4) 0.18323(9) 1.000 0.0413(7) d . . . C4 C Uani 0.3262(4) 0.8729(4) 0.17635(9) 1.000 0.0409(8) d . . . C5 C Uani 0.1573(4) 0.8353(5) 0.13003(10) 1.000 0.0417(7) d . . . C6 C Uani 0.1978(4) 0.6396(4) 0.09027(9) 1.000 0.0365(7) d . . . C7 C Uani 0.4496(4) 0.2771(4) 0.05387(8) 1.000 0.0290(6) d . . . F1B F Uani 0.0058(10) 0.9775(13) 0.1344(3) 0.210 0.053(2) d P . . H2 H Uiso 0.733(4) 0.416(5) 0.1496(10) 1.000 0.049(7) d . . . H6 H Uiso 0.085(4) 0.602(5) 0.0576(11) 1.000 0.057(8) d . . . H1 H Uiso 0.64970 0.03080 0.03500 1.000 0.0590 c 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 F1A 0.0613(11) 0.0515(11) 0.0406(9) -0.0164(8) -0.0189(8) 0.0067(9) F2 0.0822(11) 0.0394(8) 0.0473(8) -0.0167(6) 0.0257(7) -0.0034(7) O1 0.0423(9) 0.0365(9) 0.0381(8) -0.0076(7) 0.0007(6) 0.0094(7) O2 0.0458(9) 0.0401(9) 0.0306(7) -0.0037(7) -0.0054(6) 0.0076(7) C1 0.0361(11) 0.0255(10) 0.0265(10) 0.0017(8) 0.0086(8) -0.0017(8) C2 0.0415(12) 0.0315(11) 0.0293(10) 0.0002(9) 0.0033(9) -0.0021(10) C3 0.0610(15) 0.0347(12) 0.0282(11) -0.0027(9) 0.0045(10) -0.0101(11) C4 0.0605(15) 0.0287(12) 0.0364(12) -0.0053(9) 0.0220(11) -0.0049(10) C5 0.0444(13) 0.0356(12) 0.0473(13) -0.0030(10) 0.0175(10) 0.0018(11) C6 0.0371(12) 0.0363(12) 0.0366(12) -0.0038(10) 0.0057(9) 0.0004(10) C7 0.0331(11) 0.0273(10) 0.0270(10) 0.0035(8) 0.0050(8) 0.0005(8) F1B 0.032(3) 0.051(4) 0.074(4) -0.008(3) -0.004(3) 0.023(3) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C3 1.305(3) . . yes F1B C5 1.113(6) . . yes F2 C4 1.345(2) . . yes O1 C7 1.273(3) . . yes O2 C7 1.262(3) . . yes O1 H1 0.8400 . . no C1 C7 1.482(3) . . no C1 C2 1.394(3) . . no C1 C6 1.391(3) . . no C2 C3 1.377(3) . . no C3 C4 1.375(3) . . no C4 C5 1.373(3) . . no C5 C6 1.382(3) . . no C2 H2 1.02(2) . . no C6 H6 0.96(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.00 . . . no C2 C1 C6 120.35(18) . . . no C2 C1 C7 119.70(19) . . . no C6 C1 C7 119.94(18) . . . no C1 C2 C3 118.3(2) . . . no F1A C3 C4 117.06(19) . . . yes C2 C3 C4 121.0(2) . . . no F1A C3 C2 121.9(2) . . . yes F2 C4 C5 120.1(2) . . . yes C3 C4 C5 121.1(2) . . . no F2 C4 C3 118.79(19) . . . yes F1B C5 C4 107.8(4) . . . yes F1B C5 C6 133.4(4) . . . yes C4 C5 C6 118.8(2) . . . no C1 C6 C5 120.4(2) . . . no O1 C7 C1 117.54(18) . . . yes O2 C7 C1 119.15(19) . . . yes O1 C7 O2 123.31(18) . . . yes C1 C2 H2 121.6(13) . . . no C3 C2 H2 120.0(14) . . . no C1 C6 H6 117.1(15) . . . no C5 C6 H6 122.5(15) . . . no 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 C6 C1 C2 C3 -0.4(3) . . . . no C7 C1 C2 C3 179.58(19) . . . . no C2 C1 C6 C5 0.4(3) . . . . no C7 C1 C6 C5 -179.6(2) . . . . no C2 C1 C7 O1 -0.4(3) . . . . no C2 C1 C7 O2 179.77(19) . . . . no C6 C1 C7 O1 179.60(19) . . . . no C6 C1 C7 O2 -0.3(3) . . . . no C1 C2 C3 F1A -180.0(2) . . . . no C1 C2 C3 C4 0.5(3) . . . . no F1A C3 C4 F2 0.6(3) . . . . no F1A C3 C4 C5 179.8(2) . . . . no C2 C3 C4 F2 -179.77(19) . . . . no C2 C3 C4 C5 -0.6(3) . . . . no F2 C4 C5 C6 179.8(2) . . . . no C3 C4 C5 C6 0.6(3) . . . . no C4 C5 C6 C1 -0.5(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 0.8400 1.7900 2.619(2) 168.00 3_655 yes C6 H6 O2 0.96(2) 2.44(2) 2.793(3) 101.2(16) . yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; _iucr_refine_instructions_details ; ; data_datam4 _database_code_depnum_ccdc_archive 'CCDC 881261' #TrackingRef '11180_web_deposit_cif_file_3_RiteshDubey_1336563816.234TFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 F3 O2' # 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 'C7 H3 F3 O2' _chemical_formula_iupac ? _chemical_formula_weight 176.09 _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 C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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 5.112(5) _cell_length_b 5.193(5) _cell_length_c 24.39(2) _cell_angle_alpha 90 _cell_angle_beta 95.477(11) _cell_angle_gamma 90 _cell_volume 644.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 1620 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.815 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.187 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.964 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' # number of measured reflections (redundant set) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4682 2theta: 29.4305 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4682 2theta: 29.4305 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4682 2theta: 29.4305 ; _diffrn_reflns_number 6117 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.69 _diffrn_reflns_theta_full 27.69 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1496 # number of observed reflections (> n sig(I)) _reflns_number_gt 1309 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0639P)^2^+0.2781P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1496 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.345 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.062 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F Uani 0.2341(2) 0.2291(2) 0.15623(4) 1.000 0.0325(3) d . . . F3 F Uani -0.4496(2) -0.2749(2) 0.20977(5) 1.000 0.0368(4) d . . . F5 F Uani -0.1129(2) 0.1221(2) 0.22712(4) 1.000 0.0363(4) d . . . O2 O Uani 0.4002(3) 0.1431(3) 0.05908(5) 1.000 0.0314(4) d . . . O4 O Uani 0.2577(3) -0.2110(3) 0.01322(5) 1.000 0.0309(4) d . . . C6 C Uani 0.0727(3) -0.1115(3) 0.09579(6) 1.000 0.0212(5) d . . . C7 C Uani 0.0678(3) 0.0339(3) 0.14374(7) 1.000 0.0223(5) d . . . C8 C Uani -0.1100(3) -0.0209(3) 0.18165(7) 1.000 0.0247(5) d . . . C9 C Uani -0.2812(3) -0.2254(4) 0.17227(7) 1.000 0.0251(5) d . . . C10 C Uani -0.2800(4) -0.3765(4) 0.12549(8) 1.000 0.0269(5) d . . . C11 C Uani 0.2556(3) -0.0574(3) 0.05327(7) 1.000 0.0223(5) d . . . C12 C Uani -0.1039(4) -0.3174(3) 0.08767(7) 1.000 0.0244(5) d . . . H2 H Uiso 0.49300 0.15410 0.03250 1.000 0.0470 c R . . H10 H Uiso -0.399(4) -0.519(5) 0.1178(9) 1.000 0.038(6) d . . . H12 H Uiso -0.102(4) -0.412(5) 0.0554(10) 1.000 0.036(6) 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 F1 0.0344(6) 0.0330(6) 0.0312(6) -0.0099(4) 0.0096(5) -0.0154(5) F3 0.0330(6) 0.0461(7) 0.0340(6) 0.0015(5) 0.0172(5) -0.0087(5) F5 0.0405(7) 0.0427(7) 0.0275(6) -0.0120(5) 0.0132(5) -0.0078(5) O2 0.0348(7) 0.0315(7) 0.0299(7) -0.0037(5) 0.0133(5) -0.0133(6) O4 0.0344(7) 0.0353(8) 0.0245(6) -0.0075(5) 0.0104(5) -0.0089(6) C6 0.0206(8) 0.0225(8) 0.0205(8) 0.0021(6) 0.0021(6) -0.0007(6) C7 0.0219(8) 0.0210(8) 0.0237(8) -0.0007(6) 0.0012(6) -0.0043(6) C8 0.0253(8) 0.0291(9) 0.0200(8) -0.0021(6) 0.0038(6) 0.0000(7) C9 0.0204(8) 0.0305(9) 0.0253(8) 0.0053(7) 0.0068(6) -0.0008(7) C10 0.0251(9) 0.0255(9) 0.0304(9) 0.0014(7) 0.0040(7) -0.0064(7) C11 0.0228(8) 0.0233(8) 0.0210(8) 0.0000(6) 0.0027(6) -0.0017(6) C12 0.0259(8) 0.0246(9) 0.0229(8) -0.0024(6) 0.0031(6) -0.0041(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C7 1.339(2) . . yes F3 C9 1.339(2) . . yes F5 C8 1.336(2) . . yes O2 C11 1.277(3) . . yes O4 C11 1.262(2) . . yes O2 H2 0.8400 . . no C6 C11 1.488(3) . . no C6 C12 1.401(3) . . no C6 C7 1.394(3) . . no C7 C8 1.387(3) . . no C8 C9 1.381(3) . . no C9 C10 1.385(3) . . no C10 C12 1.384(3) . . no C10 H10 0.97(2) . . no C12 H12 0.93(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O2 H2 109.00 . . . no C7 C6 C11 123.04(14) . . . no C7 C6 C12 117.96(14) . . . no C11 C6 C12 119.00(14) . . . no F1 C7 C8 116.48(14) . . . yes C6 C7 C8 120.90(14) . . . no F1 C7 C6 122.61(14) . . . yes F5 C8 C7 119.96(14) . . . yes C7 C8 C9 119.52(15) . . . no F5 C8 C9 120.52(14) . . . yes F3 C9 C8 118.22(16) . . . yes C8 C9 C10 121.29(16) . . . no F3 C9 C10 120.49(17) . . . yes C9 C10 C12 118.54(18) . . . no O2 C11 O4 123.62(16) . . . yes O4 C11 C6 118.20(14) . . . yes O2 C11 C6 118.18(14) . . . yes C6 C12 C10 121.77(16) . . . no C9 C10 H10 122.8(13) . . . no C12 C10 H10 118.6(13) . . . no C6 C12 H12 117.7(14) . . . no C10 C12 H12 120.5(14) . . . no 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 C11 C6 C7 F1 -2.3(2) . . . . no C11 C6 C7 C8 178.70(15) . . . . no C12 C6 C7 F1 177.76(15) . . . . no C12 C6 C7 C8 -1.2(2) . . . . no C7 C6 C11 O2 -5.5(2) . . . . no C7 C6 C11 O4 175.07(16) . . . . no C12 C6 C11 O2 174.40(16) . . . . no C12 C6 C11 O4 -5.0(2) . . . . no C7 C6 C12 C10 0.3(3) . . . . no C11 C6 C12 C10 -179.58(16) . . . . no F1 C7 C8 F5 1.5(2) . . . . no F1 C7 C8 C9 -177.80(15) . . . . no C6 C7 C8 F5 -179.45(14) . . . . no C6 C7 C8 C9 1.2(2) . . . . no F5 C8 C9 F3 0.3(2) . . . . no F5 C8 C9 C10 -179.67(16) . . . . no C7 C8 C9 F3 179.56(15) . . . . no C7 C8 C9 C10 -0.4(3) . . . . no F3 C9 C10 C12 179.58(17) . . . . no C8 C9 C10 C12 -0.5(3) . . . . no C9 C10 C12 C6 0.5(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O2 H2 O4 0.8400 1.8000 2.623(3) 167.00 3_655 yes C10 H10 F1 0.97(2) 2.54(2) 3.359(4) 142.9(17) 1_445 yes C10 H10 O2 0.97(2) 2.43(2) 3.319(4) 153.1(18) 1_445 yes C12 H12 O4 0.93(2) 2.43(2) 2.768(4) 101.6(16) . yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; _iucr_refine_instructions_details ; ; data_datam5 _database_code_depnum_ccdc_archive 'CCDC 881262' #TrackingRef '11181_web_deposit_cif_file_4_RiteshDubey_1336563816.235TFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H2 F3 O2' # 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 'C7 H2 F3 O2' _chemical_formula_iupac ? _chemical_formula_weight 175.09 _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 C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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 3.6704(9) _cell_length_b 15.516(4) _cell_length_c 11.882(3) _cell_angle_alpha 90 _cell_angle_beta 93.734(7) _cell_angle_gamma 90 _cell_volume 675.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5078 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.178 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.982 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 # number of measured reflections (redundant set) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_reflns_number 6781 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _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 1546 # number of observed reflections (> n sig(I)) _reflns_number_gt 995 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0526P)^2^+0.2901P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1546 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.243 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.056 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1A F Uani 0.4248(4) 0.25668(9) 0.85923(11) 0.920 0.0313(5) d P . . F2 F Uani 0.1988(4) 0.34547(10) 0.68019(13) 1.000 0.0476(6) d . . . F3 F Uani -0.1985(5) 0.09293(11) 0.49258(12) 1.000 0.0514(6) d . . . O1 O Uani 0.2444(5) -0.00767(11) 0.86787(16) 1.000 0.0416(7) d . . . O2 O Uani 0.5458(5) 0.10159(11) 0.95259(14) 1.000 0.0360(6) d . . . C1 C Uani 0.2304(6) 0.12399(15) 0.77314(19) 1.000 0.0252(7) d . . . C2 C Uani 0.2724(6) 0.21245(15) 0.77176(19) 1.000 0.0268(7) d . . . C3 C Uani 0.1536(7) 0.25956(16) 0.6774(2) 1.000 0.0313(8) d . . . C4 C Uani -0.0067(7) 0.22113(18) 0.5827(2) 1.000 0.0342(8) d . . . C5 C Uani -0.0402(7) 0.13309(18) 0.5850(2) 1.000 0.0343(9) d . . . C6 C Uani 0.0689(7) 0.08305(17) 0.6767(2) 1.000 0.0311(8) d . . . C7 C Uani 0.3556(6) 0.07179(15) 0.8737(2) 1.000 0.0273(7) d . . . F1B F Uani 0.021(5) 0.0171(11) 0.6729(14) 0.080 0.040(6) d P . . H1 H Uiso 0.311(12) -0.038(3) 0.940(4) 1.000 0.133(16) d . . . H4 H Uiso -0.085(7) 0.2538(18) 0.519(2) 1.000 0.044(8) 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 F1A 0.0434(9) 0.0234(8) 0.0259(8) -0.0008(6) -0.0072(7) -0.0017(7) F2 0.0610(11) 0.0305(9) 0.0502(10) 0.0135(7) -0.0045(8) 0.0013(7) F3 0.0599(11) 0.0624(11) 0.0295(9) -0.0083(7) -0.0161(7) 0.0058(9) O1 0.0542(12) 0.0256(10) 0.0424(12) 0.0065(8) -0.0164(9) -0.0072(9) O2 0.0471(11) 0.0281(9) 0.0306(10) 0.0038(8) -0.0134(8) -0.0044(9) C1 0.0233(12) 0.0262(13) 0.0259(13) 0.0022(9) 0.0005(10) 0.0045(10) C2 0.0254(12) 0.0309(13) 0.0238(13) 0.0000(10) 0.0002(10) 0.0020(10) C3 0.0313(13) 0.0290(14) 0.0338(14) 0.0065(10) 0.0046(11) 0.0042(11) C4 0.0334(14) 0.0436(16) 0.0255(14) 0.0094(11) 0.0005(11) 0.0093(12) C5 0.0308(14) 0.0493(17) 0.0220(13) -0.0033(11) -0.0041(10) 0.0066(12) C6 0.0324(14) 0.0330(16) 0.0275(13) -0.0013(11) -0.0011(10) 0.0030(12) C7 0.0279(12) 0.0229(12) 0.0304(14) 0.0002(10) -0.0023(10) 0.0010(10) F1B 0.059(12) 0.020(9) 0.040(11) 0.005(7) -0.002(9) 0.001(9) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C2 1.337(3) . . yes F1B C6 1.039(17) . . yes F2 C3 1.343(3) . . yes F3 C5 1.360(3) . . yes O1 C7 1.299(3) . . yes O2 C7 1.223(3) . . yes O1 H1 0.99(5) . . no C1 C7 1.491(3) . . no C1 C2 1.381(3) . . no C1 C6 1.407(3) . . no C2 C3 1.385(3) . . no C3 C4 1.372(3) . . no C4 C5 1.372(4) . . no C5 C6 1.376(4) . . no C4 H4 0.94(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 110(3) . . . no C2 C1 C6 118.7(2) . . . no C6 C1 C7 119.9(2) . . . no C2 C1 C7 121.4(2) . . . no F1A C2 C1 122.8(2) . . . yes C1 C2 C3 120.3(2) . . . no F1A C2 C3 116.9(2) . . . yes F2 C3 C4 119.8(2) . . . yes C2 C3 C4 122.0(2) . . . no F2 C3 C2 118.2(2) . . . yes C3 C4 C5 116.8(2) . . . no F3 C5 C4 118.3(2) . . . yes F3 C5 C6 117.9(2) . . . yes C4 C5 C6 123.8(2) . . . no F1B C6 C1 122.8(10) . . . yes F1B C6 C5 118.8(10) . . . yes C1 C6 C5 118.4(2) . . . no O1 C7 C1 113.2(2) . . . yes O2 C7 C1 122.7(2) . . . yes O1 C7 O2 124.2(2) . . . yes C3 C4 H4 121.2(17) . . . no C5 C4 H4 122.0(16) . . . no 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 C6 C1 C2 F1A -179.6(2) . . . . no C6 C1 C2 C3 0.7(3) . . . . no C7 C1 C2 F1A -0.2(3) . . . . no C7 C1 C2 C3 -179.9(2) . . . . no C2 C1 C6 C5 0.0(4) . . . . no C7 C1 C6 C5 -179.4(2) . . . . no C2 C1 C7 O1 169.7(2) . . . . no C2 C1 C7 O2 -10.8(3) . . . . no C6 C1 C7 O1 -10.9(3) . . . . no C6 C1 C7 O2 168.6(2) . . . . no F1A C2 C3 F2 -0.1(3) . . . . no F1A C2 C3 C4 180.0(2) . . . . no C1 C2 C3 F2 179.7(2) . . . . no C1 C2 C3 C4 -0.3(4) . . . . no F2 C3 C4 C5 179.2(2) . . . . no C2 C3 C4 C5 -0.8(4) . . . . no C3 C4 C5 F3 179.9(2) . . . . no C3 C4 C5 C6 1.6(4) . . . . no F3 C5 C6 C1 -179.5(2) . . . . no C4 C5 C6 C1 -1.2(4) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 0.99(5) 1.67(5) 2.656(3) 170(4) 3_657 yes C4 H4 F1A 0.94(3) 2.53(2) 3.287(3) 137(2) 4_454 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; _iucr_refine_instructions_details ; ; data_datam6 _database_code_depnum_ccdc_archive 'CCDC 881263' #TrackingRef '11182_web_deposit_cif_file_5_RiteshDubey_1336563816.236TFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H2 F3 O2' # 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 'C7 H2 F3 O2' _chemical_formula_iupac ? _chemical_formula_weight 175.09 _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 C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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 6.9301(11) _cell_length_b 13.517(2) _cell_length_c 7.0809(12) _cell_angle_alpha 90 _cell_angle_beta 94.132(7) _cell_angle_gamma 90 _cell_volume 661.57(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5390 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.182 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.982 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 # number of measured reflections (redundant set) _diffrn_reflns_number 6431 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _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 1512 # number of observed reflections (> n sig(I)) _reflns_number_gt 1162 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0641P)^2^+0.2538P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1512 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1200 _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 0.239 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.057 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F Uani 0.04642(17) 0.38231(9) 0.16070(19) 1.000 0.0426(4) d . . . F2 F Uani -0.50247(17) 0.18276(9) -0.00580(19) 1.000 0.0404(4) d . . . F3A F Uani -0.2935(2) 0.02243(10) 0.0779(2) 0.880 0.0441(5) d P . . O1 O Uani -0.5026(2) 0.37463(12) -0.0745(2) 1.000 0.0448(5) d . . . O2 O Uani -0.3091(2) 0.45809(11) 0.1322(2) 1.000 0.0460(5) d . . . C1 C Uani -0.2376(3) 0.28961(14) 0.0794(3) 1.000 0.0275(6) d . . . C2 C Uani -0.0409(3) 0.29373(14) 0.1415(3) 1.000 0.0309(6) d . . . C3 C Uani 0.0714(3) 0.21046(16) 0.1801(3) 1.000 0.0356(7) d . . . C4 C Uani -0.0149(3) 0.11802(16) 0.1584(3) 1.000 0.0371(7) d . . . C5 C Uani -0.2068(3) 0.11132(14) 0.0960(3) 1.000 0.0345(6) d . . . C6 C Uani -0.3161(3) 0.19515(14) 0.0546(3) 1.000 0.0302(6) d . . . C7 C Uani -0.3546(3) 0.38154(14) 0.0459(3) 1.000 0.0282(6) d . . . F3B F Uani 0.2207(16) 0.2184(9) 0.2320(18) 0.120 0.050(4) d P . . H1 H Uiso -0.574(6) 0.433(3) -0.085(6) 1.000 0.114(14) d . . . H4 H Uiso 0.053(4) 0.0591(19) 0.189(3) 1.000 0.050(7) 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 F1 0.0342(7) 0.0333(7) 0.0593(8) -0.0013(6) -0.0031(6) -0.0035(5) F2 0.0326(7) 0.0303(7) 0.0573(9) -0.0019(6) -0.0043(6) -0.0008(5) F3A 0.0510(9) 0.0198(7) 0.0601(10) -0.0024(6) -0.0053(7) 0.0024(6) O1 0.0462(10) 0.0320(8) 0.0528(10) -0.0108(7) -0.0189(8) 0.0149(7) O2 0.0447(9) 0.0273(8) 0.0628(11) -0.0112(7) -0.0171(8) 0.0079(7) C1 0.0295(10) 0.0260(10) 0.0271(10) -0.0002(7) 0.0031(8) 0.0057(7) C2 0.0329(11) 0.0291(10) 0.0310(10) -0.0017(8) 0.0041(8) 0.0010(8) C3 0.0336(12) 0.0400(12) 0.0332(11) 0.0010(9) 0.0032(9) 0.0109(9) C4 0.0436(13) 0.0310(11) 0.0368(11) 0.0020(9) 0.0037(9) 0.0155(9) C5 0.0439(12) 0.0227(10) 0.0369(11) -0.0017(8) 0.0032(9) 0.0037(8) C6 0.0293(10) 0.0286(10) 0.0326(11) -0.0020(8) 0.0008(8) 0.0038(8) C7 0.0299(10) 0.0254(10) 0.0290(10) -0.0011(8) 0.0004(8) 0.0032(7) F3B 0.031(6) 0.060(7) 0.059(8) -0.003(6) -0.004(5) 0.015(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.344(2) . . yes F2 C6 1.342(2) . . yes F3A C5 1.345(2) . . yes F3B C3 1.078(12) . . yes O1 C7 1.289(3) . . yes O2 C7 1.231(2) . . yes O1 H1 0.93(4) . . no C1 C7 1.493(3) . . no C1 C2 1.403(3) . . no C1 C6 1.394(3) . . no C2 C3 1.384(3) . . no C3 C4 1.389(3) . . no C4 C5 1.374(3) . . no C5 C6 1.383(3) . . no C4 H4 0.94(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 113(3) . . . no C2 C1 C6 115.94(18) . . . no C6 C1 C7 122.66(19) . . . no C2 C1 C7 121.40(17) . . . no F1 C2 C1 119.16(17) . . . yes C1 C2 C3 123.32(18) . . . no F1 C2 C3 117.50(18) . . . yes F3B C3 C2 119.9(7) . . . yes F3B C3 C4 121.5(7) . . . yes C2 C3 C4 118.56(19) . . . no C3 C4 C5 119.60(19) . . . no F3A C5 C4 120.32(18) . . . yes F3A C5 C6 118.53(18) . . . yes C4 C5 C6 121.13(19) . . . no F2 C6 C5 117.74(17) . . . yes C1 C6 C5 121.40(19) . . . no F2 C6 C1 120.83(17) . . . yes O1 C7 C1 116.22(17) . . . yes O2 C7 C1 120.25(19) . . . yes O1 C7 O2 123.53(19) . . . yes C3 C4 H4 122.1(16) . . . no C5 C4 H4 118.3(16) . . . no 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 C6 C1 C2 F1 177.19(18) . . . . no C6 C1 C2 C3 -1.1(3) . . . . no C7 C1 C2 F1 -3.9(3) . . . . no C7 C1 C2 C3 177.9(2) . . . . no C2 C1 C6 F2 -179.47(18) . . . . no C2 C1 C6 C5 2.3(3) . . . . no C7 C1 C6 F2 1.6(3) . . . . no C7 C1 C6 C5 -176.6(2) . . . . no C2 C1 C7 O1 154.1(2) . . . . no C2 C1 C7 O2 -26.5(3) . . . . no C6 C1 C7 O1 -27.0(3) . . . . no C6 C1 C7 O2 152.3(2) . . . . no F1 C2 C3 C4 -179.01(19) . . . . no C1 C2 C3 C4 -0.7(3) . . . . no C2 C3 C4 C5 1.3(3) . . . . no C3 C4 C5 F3A -178.66(19) . . . . no C3 C4 C5 C6 -0.1(3) . . . . no F3A C5 C6 F2 -1.5(3) . . . . no F3A C5 C6 C1 176.77(19) . . . . no C4 C5 C6 F2 179.94(19) . . . . no C4 C5 C6 C1 -1.8(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 0.93(4) 1.70(4) 2.628(2) 172(4) 3_465 yes C4 H4 O2 0.94(3) 2.51(3) 3.381(3) 154(2) 2_545 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; _iucr_refine_instructions_details ; ; data_datam7 _database_code_depnum_ccdc_archive 'CCDC 881264' #TrackingRef '11183_web_deposit_cif_file_6_RiteshDubey_1336563816.245TFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 F3 O2' # 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 'C7 H3 F3 O2' _chemical_formula_iupac ? _chemical_formula_weight 176.09 _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 C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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 7.1042(7) _cell_length_b 7.1852(7) _cell_length_c 12.8037(13) _cell_angle_alpha 90 _cell_angle_beta 102.453(7) _cell_angle_gamma 90 _cell_volume 638.19(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5589 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.080 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.189 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.985 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' # number of measured reflections (redundant set) _diffrn_reflns_number 6560 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1466 # number of observed reflections (> n sig(I)) _reflns_number_gt 1208 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0481P)^2^+0.2272P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1466 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.290 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.048 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F Uani 0.49899(13) 0.68206(13) 0.53915(7) 1.000 0.0263(3) d . . . F2 F Uani -0.02073(12) 0.74926(14) 0.24767(7) 1.000 0.0301(3) d . . . F3 F Uani 0.19238(12) 0.95942(13) 0.14497(7) 1.000 0.0267(3) d . . . O1 O Uani 0.82859(14) 1.03133(15) 0.39555(8) 1.000 0.0242(3) d . . . O2 O Uani 0.82773(16) 0.82117(16) 0.52381(9) 1.000 0.0282(3) d . . . C1 C Uani 0.54458(19) 0.85870(19) 0.38989(11) 1.000 0.0171(4) d . . . C2 C Uani 0.4297(2) 0.74891(19) 0.44061(11) 1.000 0.0185(4) d . . . C3 C Uani 0.2393(2) 0.7084(2) 0.39408(12) 1.000 0.0226(4) d . . . C4 C Uani 0.16316(19) 0.7824(2) 0.29515(12) 1.000 0.0211(4) d . . . C5 C Uani 0.2733(2) 0.8920(2) 0.24228(11) 1.000 0.0192(4) d . . . C6 C Uani 0.4616(2) 0.9300(2) 0.28864(11) 1.000 0.0188(4) d . . . C7 C Uani 0.7475(2) 0.91146(18) 0.43692(11) 1.000 0.0176(4) d . . . H2 H Uiso 0.944(3) 0.864(3) 0.5480(16) 1.000 0.043(6) d . . . H3 H Uiso 0.162(2) 0.632(2) 0.4318(13) 1.000 0.020(4) d . . . H6 H Uiso 0.534(2) 1.001(2) 0.2492(14) 1.000 0.026(4) 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 F1 0.0267(5) 0.0326(5) 0.0178(4) 0.0065(4) 0.0010(3) -0.0045(4) F2 0.0146(4) 0.0474(6) 0.0261(5) -0.0060(4) -0.0004(3) -0.0056(4) F3 0.0232(5) 0.0354(5) 0.0180(4) 0.0027(4) -0.0031(3) 0.0037(4) O1 0.0190(5) 0.0290(6) 0.0221(5) 0.0059(4) -0.0012(4) -0.0055(4) O2 0.0199(5) 0.0329(6) 0.0260(6) 0.0100(5) -0.0076(4) -0.0073(5) C1 0.0162(7) 0.0167(6) 0.0172(6) -0.0028(5) 0.0007(5) 0.0005(5) C2 0.0198(7) 0.0202(7) 0.0145(7) -0.0015(5) 0.0017(5) 0.0009(5) C3 0.0209(7) 0.0268(8) 0.0208(7) -0.0033(6) 0.0059(6) -0.0050(6) C4 0.0139(6) 0.0260(7) 0.0220(7) -0.0075(6) 0.0008(5) -0.0009(5) C5 0.0195(7) 0.0212(7) 0.0148(6) -0.0018(5) -0.0007(5) 0.0037(5) C6 0.0196(7) 0.0185(7) 0.0176(7) 0.0001(5) 0.0024(5) -0.0010(5) C7 0.0176(7) 0.0177(6) 0.0162(7) -0.0021(5) 0.0008(5) 0.0007(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.3405(16) . . yes F2 C4 1.3381(17) . . yes F3 C5 1.3448(17) . . yes O1 C7 1.2190(17) . . yes O2 C7 1.3077(18) . . yes O2 H2 0.87(2) . . no C1 C6 1.400(2) . . no C1 C7 1.487(2) . . no C1 C2 1.392(2) . . no C2 C3 1.386(2) . . no C3 C4 1.373(2) . . no C4 C5 1.385(2) . . no C5 C6 1.369(2) . . no C3 H3 0.975(15) . . no C6 H6 0.944(16) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 H2 109.4(14) . . . no C2 C1 C6 117.84(13) . . . no C2 C1 C7 124.77(12) . . . no C6 C1 C7 117.36(12) . . . no F1 C2 C3 117.10(13) . . . yes C1 C2 C3 122.29(13) . . . no F1 C2 C1 120.58(13) . . . yes C2 C3 C4 117.97(13) . . . no F2 C4 C5 118.57(13) . . . yes C3 C4 C5 121.29(13) . . . no F2 C4 C3 120.14(13) . . . yes F3 C5 C6 120.82(13) . . . yes C4 C5 C6 120.24(13) . . . no F3 C5 C4 118.94(13) . . . yes C1 C6 C5 120.36(13) . . . no O1 C7 C1 120.80(12) . . . yes O2 C7 C1 115.14(12) . . . yes O1 C7 O2 124.06(13) . . . yes C2 C3 H3 120.5(9) . . . no C4 C3 H3 121.6(9) . . . no C1 C6 H6 121.6(10) . . . no C5 C6 H6 118.0(10) . . . no 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 C6 C1 C2 F1 -177.68(12) . . . . no C6 C1 C2 C3 0.3(2) . . . . no C7 C1 C2 F1 0.1(2) . . . . no C7 C1 C2 C3 178.12(13) . . . . no C2 C1 C6 C5 0.2(2) . . . . no C7 C1 C6 C5 -177.80(13) . . . . no C2 C1 C7 O1 -168.11(14) . . . . no C2 C1 C7 O2 11.7(2) . . . . no C6 C1 C7 O1 9.7(2) . . . . no C6 C1 C7 O2 -170.56(13) . . . . no F1 C2 C3 C4 177.20(13) . . . . no C1 C2 C3 C4 -0.9(2) . . . . no C2 C3 C4 F2 -179.10(13) . . . . no C2 C3 C4 C5 1.0(2) . . . . no F2 C4 C5 F3 -0.7(2) . . . . no F2 C4 C5 C6 179.55(13) . . . . no C3 C4 C5 F3 179.27(13) . . . . no C3 C4 C5 C6 -0.5(2) . . . . no F3 C5 C6 C1 -179.84(13) . . . . no C4 C5 C6 C1 -0.1(2) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O2 H2 O1 0.87(2) 1.79(2) 2.6577(16) 174.3(18) 3_776 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; _iucr_refine_instructions_details ; ; data_345fba _database_code_depnum_ccdc_archive 'CCDC 881265' #TrackingRef '11184_web_deposit_cif_file_7_RiteshDubey_1336563816.345TFBA_I.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 F3 O2' # 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 'C7 H3 F3 O2' _chemical_formula_iupac ? _chemical_formula_weight 176.09 _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 5.1190(14) _cell_length_b 6.4295(17) _cell_length_c 20.343(6) _cell_angle_alpha 90 _cell_angle_beta 95.574(7) _cell_angle_gamma 90 _cell_volume 666.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.181 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9612 _exptl_absorpt_correction_T_max 0.9733 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' # number of measured reflections (redundant set) _diffrn_reflns_number 5694 _diffrn_reflns_av_R_equivalents 0.0819 _diffrn_reflns_av_sigmaI/netI 0.0673 _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 -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_reduction_process ; ; _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _reflns_number_total 1532 _reflns_number_gt 943 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 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^)+(0.0707P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1532 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1015 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.250 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.062 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F1 F Uani 0.9738(3) 0.0971(3) 0.11719(9) 1.000 0.0509(6) . . F2 F Uani 0.6469(3) 0.0479(3) 0.21113(9) 1.000 0.0509(6) . . F3 F Uani 0.2941(3) 0.3432(3) 0.23237(8) 1.000 0.0537(7) . . O1 O Uani 0.3985(4) 0.8909(3) 0.06266(10) 1.000 0.0433(7) . . O2 O Uani 0.7307(4) 0.7741(3) 0.00924(10) 1.000 0.0410(7) . . C1 C Uani 0.7870(5) 0.4228(4) 0.08712(14) 1.000 0.0354(9) . . C2 C Uani 0.6004(5) 0.5732(4) 0.09739(14) 1.000 0.0342(8) . . C3 C Uani 0.4329(5) 0.5493(4) 0.14660(14) 1.000 0.0365(9) . . C4 C Uani 0.6326(5) 0.2214(4) 0.17444(15) 1.000 0.0379(9) . . C5 C Uani 0.4531(5) 0.3725(4) 0.18445(14) 1.000 0.0373(9) . . C6 C Uani 0.5678(5) 0.7614(4) 0.05501(13) 1.000 0.0346(8) . . C7 C Uani 0.7985(5) 0.2480(4) 0.12578(15) 1.000 0.0375(9) . . H1 H Uiso 0.90138 0.44038 0.05474 1.000 0.0425 . . H2 H Uiso 0.69685 0.87815 -0.01331 1.000 0.0615 . . H3 H Uiso 0.30958 0.65104 0.15374 1.000 0.0438 . . 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 F1 0.0456(10) 0.0419(10) 0.0675(12) 0.0033(8) 0.0166(8) 0.0160(8) F2 0.0493(10) 0.0436(10) 0.0607(12) 0.0163(8) 0.0098(8) 0.0050(8) F3 0.0532(11) 0.0553(12) 0.0565(12) 0.0086(9) 0.0250(9) 0.0066(9) O1 0.0440(11) 0.0355(11) 0.0522(13) 0.0045(9) 0.0139(9) 0.0126(10) O2 0.0409(11) 0.0363(12) 0.0475(13) 0.0039(9) 0.0125(9) 0.0075(9) C1 0.0300(14) 0.0347(15) 0.0425(17) -0.0001(12) 0.0085(12) 0.0006(12) C2 0.0310(14) 0.0310(14) 0.0403(16) -0.0037(12) 0.0020(12) 0.0036(12) C3 0.0300(14) 0.0355(15) 0.0448(17) -0.0059(13) 0.0078(12) 0.0036(12) C4 0.0359(14) 0.0335(15) 0.0438(17) 0.0031(12) 0.0013(13) 0.0010(13) C5 0.0320(14) 0.0402(16) 0.0413(16) -0.0029(13) 0.0116(12) -0.0017(13) C6 0.0306(13) 0.0362(15) 0.0376(16) -0.0069(12) 0.0067(12) 0.0029(12) C7 0.0282(13) 0.0352(16) 0.0493(18) -0.0054(13) 0.0046(12) 0.0077(13) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C7 1.345(3) . . yes F2 C4 1.340(3) . . yes F3 C5 1.343(3) . . yes O1 C6 1.223(3) . . yes O2 C6 1.311(3) . . yes O2 H2 0.8200 . . no C1 C7 1.370(4) . . no C1 C2 1.389(4) . . no C2 C3 1.388(4) . . no C2 C6 1.486(4) . . no C3 C5 1.371(4) . . no C4 C5 1.366(4) . . no C4 C7 1.376(4) . . no C1 H1 0.9300 . . no C3 H3 0.9300 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 H2 109.00 . . . no C2 C1 C7 118.5(3) . . . no C1 C2 C3 120.9(2) . . . no C3 C2 C6 117.8(2) . . . no C1 C2 C6 121.3(2) . . . no C2 C3 C5 118.6(2) . . . no F2 C4 C5 120.7(2) . . . yes F2 C4 C7 120.0(2) . . . yes C5 C4 C7 119.3(3) . . . no F3 C5 C3 120.4(2) . . . yes F3 C5 C4 118.2(2) . . . yes C3 C5 C4 121.4(3) . . . no O1 C6 C2 121.5(2) . . . yes O2 C6 C2 114.8(2) . . . yes O1 C6 O2 123.7(2) . . . yes F1 C7 C4 118.0(2) . . . yes C1 C7 C4 121.3(2) . . . no F1 C7 C1 120.6(2) . . . yes C2 C1 H1 121.00 . . . no C7 C1 H1 121.00 . . . no C2 C3 H3 121.00 . . . no C5 C3 H3 121.00 . . . no 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 C7 C1 C2 C3 1.3(4) . . . . no C7 C1 C2 C6 -176.8(2) . . . . no C2 C1 C7 F1 179.3(2) . . . . no C2 C1 C7 C4 -0.9(4) . . . . no C1 C2 C3 C5 -0.8(4) . . . . no C6 C2 C3 C5 177.4(2) . . . . no C1 C2 C6 O1 177.8(3) . . . . no C1 C2 C6 O2 -1.4(4) . . . . no C3 C2 C6 O1 -0.5(4) . . . . no C3 C2 C6 O2 -179.6(2) . . . . no C2 C3 C5 F3 -179.8(2) . . . . no C2 C3 C5 C4 -0.2(4) . . . . no F2 C4 C5 F3 0.7(4) . . . . no F2 C4 C5 C3 -178.9(2) . . . . no C7 C4 C5 F3 -179.8(2) . . . . no C7 C4 C5 C3 0.7(4) . . . . no F2 C4 C7 F1 -0.7(4) . . . . no F2 C4 C7 C1 179.4(2) . . . . no C5 C4 C7 F1 179.8(2) . . . . no C5 C4 C7 C1 -0.1(4) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F1 F2 2.678(3) . . no F1 O1 2.861(3) . 1_645 no F1 O2 3.186(3) . 1_545 no F1 C5 3.221(3) . 1_655 no F1 C6 3.173(3) . 1_545 no F2 F3 2.942(2) . 2_545 no F2 F1 2.678(3) . . no F2 F3 2.684(3) . . no F2 C4 3.254(4) . 2_645 no F2 C5 3.022(3) . 2_645 no F3 C7 3.232(3) . 1_455 no F3 F2 2.684(3) . . no F3 F2 2.942(2) . 2_555 no F1 H2 2.8300 . 3_765 no F3 H3 2.7200 . 2_545 no O1 F1 2.861(3) . 1_465 no O1 C4 3.255(4) . 1_565 no O1 C7 3.256(3) . 1_565 no O1 C6 3.292(3) . 3_675 no O1 O1 3.172(3) . 3_675 no O1 O2 2.651(3) . 3_675 no O2 O1 2.651(3) . 3_675 no O2 F1 3.186(3) . 1_565 no O2 C1 3.385(3) . 3_665 no O1 H2 1.8300 . 3_675 no O1 H3 2.4900 . . no O2 H1 2.4600 . . no O2 H1 2.7600 . 3_765 no C1 C3 3.504(4) . 1_655 no C1 O2 3.385(3) . 3_665 no C1 C6 3.470(4) . 3_665 no C3 C1 3.504(4) . 1_455 no C4 O1 3.255(4) . 1_545 no C4 F2 3.254(4) . 2_655 no C5 F1 3.221(3) . 1_455 no C5 C7 3.538(4) . 1_455 no C5 F2 3.022(3) . 2_655 no C6 F1 3.173(3) . 1_565 no C6 C7 3.595(4) . 1_565 no C6 O1 3.292(3) . 3_675 no C6 C1 3.470(4) . 3_665 no C7 C5 3.538(4) . 1_655 no C7 F3 3.232(3) . 1_655 no C7 O1 3.256(3) . 1_545 no C7 C6 3.595(4) . 1_545 no C6 H2 2.7800 . 3_675 no H1 O2 2.4600 . . no H1 O2 2.7600 . 3_765 no H2 F1 2.8300 . 3_765 no H2 O1 1.8300 . 3_675 no H2 C6 2.7800 . 3_675 no H3 O1 2.4900 . . no H3 F3 2.7200 . 2_555 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O2 H2 O1 0.8200 1.8300 2.651(3) 177.00 3_675 yes data_datam9 _database_code_depnum_ccdc_archive 'CCDC 881266' #TrackingRef '11185_web_deposit_cif_file_8_RiteshDubey_1336563816.345TFBA_II.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 F3 O2' # 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 'C7 H3 F3 O2' _chemical_formula_iupac ? _chemical_formula_weight 176.09 _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 C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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 6.5824(9) _cell_length_b 8.3582(11) _cell_length_c 12.7456(17) _cell_angle_alpha 105.719(7) _cell_angle_beta 91.945(7) _cell_angle_gamma 98.065(7) _cell_volume 666.42(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5913 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.50 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.120 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.181 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.979 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 # number of measured reflections (redundant set) _diffrn_reflns_number 7029 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3058 # number of observed reflections (> n sig(I)) _reflns_number_gt 2315 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0496P)^2^+0.2153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 3058 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.212 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F Uani 0.30708(17) 0.78145(15) 0.77814(10) 1.000 0.0380(4) d . . . F2 F Uani 0.22637(19) 1.09131(15) 0.78976(10) 1.000 0.0415(4) d . . . F3 F Uani -0.1257(2) 1.18887(15) 0.86766(10) 1.000 0.0435(4) d . . . O1 O Uani -0.4814(2) 0.71020(18) 0.98681(11) 1.000 0.0348(5) d . . . O2 O Uani -0.2863(2) 0.50709(17) 0.93512(12) 1.000 0.0372(5) d . . . C1 C Uani -0.1849(3) 0.7661(2) 0.89628(14) 1.000 0.0264(5) d . . . C2 C Uani -0.0048(3) 0.7142(2) 0.85462(15) 1.000 0.0271(6) d . . . C3 C Uani 0.1293(3) 0.8243(2) 0.81745(15) 1.000 0.0283(6) d . . . C4 C Uani 0.0890(3) 0.9837(2) 0.82231(14) 1.000 0.0299(6) d . . . C5 C Uani -0.0910(3) 1.0322(2) 0.86267(15) 1.000 0.0310(6) d . . . C6 C Uani -0.2299(3) 0.9261(2) 0.89970(15) 1.000 0.0290(6) d . . . C7 C Uani -0.3257(3) 0.6509(2) 0.94174(14) 1.000 0.0271(5) d . . . F4 F Uani 0.21462(18) 0.34235(16) 0.39922(10) 1.000 0.0408(4) d . . . F5 F Uani 0.10176(16) 0.46193(14) 0.60371(10) 1.000 0.0373(4) d . . . F6 F Uani 0.31947(18) 0.42597(14) 0.77585(9) 1.000 0.0372(4) d . . . O3 O Uani 0.8753(2) 0.10550(18) 0.61883(11) 1.000 0.0314(4) d . . . O4 O Uani 0.8387(2) 0.08222(18) 0.43992(11) 1.000 0.0324(4) d . . . C8 C Uani 0.6069(3) 0.2224(2) 0.55492(15) 1.000 0.0233(5) d . . . C9 C Uani 0.4943(3) 0.2412(2) 0.46558(16) 1.000 0.0256(5) d . . . C10 C Uani 0.3258(3) 0.3216(2) 0.48333(16) 1.000 0.0268(6) d . . . C11 C Uani 0.2671(3) 0.3839(2) 0.58794(16) 1.000 0.0277(5) d . . . C12 C Uani 0.3804(3) 0.3648(2) 0.67548(15) 1.000 0.0255(5) d . . . C13 C Uani 0.5505(3) 0.2841(2) 0.66102(15) 1.000 0.0250(5) d . . . C14 C Uani 0.7848(3) 0.1305(2) 0.53322(15) 1.000 0.0238(5) d . . . H1 H Uiso -0.55120 0.63710 1.01050 1.000 0.0520 c R . . H2 H Uiso 0.027(3) 0.602(3) 0.8537(18) 1.000 0.040(6) d . . . H6 H Uiso -0.354(3) 0.964(3) 0.9294(17) 1.000 0.034(6) d . . . H3 H Uiso 0.96920 0.04780 0.59920 1.000 0.0470 c R . . H9 H Uiso 0.534(3) 0.204(2) 0.3923(17) 1.000 0.026(5) d . . . H13 H Uiso 0.626(3) 0.274(3) 0.7219(17) 1.000 0.029(5) 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 F1 0.0316(6) 0.0451(7) 0.0408(7) 0.0153(5) 0.0115(5) 0.0089(5) F2 0.0496(7) 0.0354(7) 0.0386(7) 0.0147(5) 0.0059(6) -0.0053(5) F3 0.0670(9) 0.0267(6) 0.0420(7) 0.0132(5) 0.0089(6) 0.0160(6) O1 0.0369(8) 0.0344(8) 0.0357(8) 0.0109(6) 0.0142(6) 0.0094(6) O2 0.0394(8) 0.0282(8) 0.0461(8) 0.0114(6) 0.0118(7) 0.0081(6) C1 0.0305(9) 0.0255(9) 0.0210(8) 0.0030(7) 0.0007(7) 0.0043(8) C2 0.0305(10) 0.0253(10) 0.0253(9) 0.0056(7) 0.0024(8) 0.0070(8) C3 0.0275(9) 0.0339(11) 0.0235(9) 0.0072(8) 0.0029(7) 0.0063(8) C4 0.0386(11) 0.0272(10) 0.0219(9) 0.0077(7) 0.0005(8) -0.0024(8) C5 0.0464(12) 0.0234(10) 0.0234(9) 0.0063(7) -0.0007(8) 0.0069(8) C6 0.0346(10) 0.0298(10) 0.0229(9) 0.0051(8) 0.0026(8) 0.0104(8) C7 0.0301(9) 0.0262(10) 0.0234(9) 0.0032(7) 0.0040(8) 0.0061(8) F4 0.0374(6) 0.0517(8) 0.0404(7) 0.0187(6) -0.0026(5) 0.0201(6) F5 0.0281(6) 0.0370(7) 0.0504(7) 0.0104(5) 0.0061(5) 0.0202(5) F6 0.0418(7) 0.0377(7) 0.0330(6) 0.0040(5) 0.0121(5) 0.0190(5) O3 0.0271(7) 0.0385(8) 0.0317(7) 0.0093(6) 0.0033(6) 0.0164(6) O4 0.0296(7) 0.0408(8) 0.0310(7) 0.0104(6) 0.0081(6) 0.0172(6) C8 0.0201(8) 0.0198(9) 0.0309(9) 0.0084(7) 0.0033(7) 0.0027(7) C9 0.0251(9) 0.0235(9) 0.0292(10) 0.0086(8) 0.0058(8) 0.0039(7) C10 0.0226(9) 0.0267(10) 0.0343(10) 0.0137(8) -0.0006(8) 0.0048(7) C11 0.0194(8) 0.0205(9) 0.0439(11) 0.0084(8) 0.0051(8) 0.0062(7) C12 0.0255(9) 0.0208(9) 0.0293(9) 0.0040(7) 0.0080(7) 0.0052(7) C13 0.0251(9) 0.0229(9) 0.0275(9) 0.0064(7) 0.0028(7) 0.0060(7) C14 0.0197(8) 0.0226(9) 0.0287(9) 0.0061(7) 0.0025(7) 0.0044(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C3 1.345(2) . . yes F2 C4 1.341(2) . . yes F3 C5 1.346(2) . . yes F4 C10 1.341(2) . . yes F5 C11 1.339(2) . . yes F6 C12 1.340(2) . . yes O1 C7 1.286(2) . . yes O2 C7 1.246(2) . . yes O1 H1 0.8400 . . no O3 C14 1.305(2) . . yes O4 C14 1.230(2) . . yes O3 H3 0.8400 . . no C1 C7 1.487(3) . . no C1 C6 1.400(3) . . no C1 C2 1.392(3) . . no C2 C3 1.374(3) . . no C3 C4 1.380(3) . . no C4 C5 1.377(3) . . no C5 C6 1.369(3) . . no C2 H2 0.99(3) . . no C6 H6 0.97(2) . . no C8 C13 1.394(3) . . no C8 C14 1.482(3) . . no C8 C9 1.394(3) . . no C9 C10 1.370(3) . . no C10 C11 1.383(3) . . no C11 C12 1.378(3) . . no C12 C13 1.379(3) . . no C9 H9 0.96(2) . . no C13 H13 0.94(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.00 . . . no C14 O3 H3 109.00 . . . no C2 C1 C6 121.04(17) . . . no C6 C1 C7 120.16(17) . . . no C2 C1 C7 118.75(16) . . . no C1 C2 C3 118.46(16) . . . no C2 C3 C4 121.17(18) . . . no F1 C3 C2 120.83(16) . . . yes F1 C3 C4 117.98(16) . . . yes C3 C4 C5 119.56(17) . . . no F2 C4 C3 120.03(17) . . . yes F2 C4 C5 120.40(16) . . . yes C4 C5 C6 121.25(17) . . . no F3 C5 C6 120.30(17) . . . yes F3 C5 C4 118.42(16) . . . yes C1 C6 C5 118.51(18) . . . no O2 C7 C1 119.27(17) . . . yes O1 C7 O2 124.61(17) . . . yes O1 C7 C1 116.12(16) . . . yes C3 C2 H2 121.0(12) . . . no C1 C2 H2 120.6(12) . . . no C1 C6 H6 121.7(15) . . . no C5 C6 H6 119.8(15) . . . no C9 C8 C13 121.00(18) . . . no C9 C8 C14 117.88(17) . . . no C13 C8 C14 121.09(17) . . . no C8 C9 C10 118.97(18) . . . no F4 C10 C11 118.53(17) . . . yes C9 C10 C11 121.00(18) . . . no F4 C10 C9 120.47(17) . . . yes F5 C11 C12 120.49(17) . . . yes C10 C11 C12 119.34(18) . . . no F5 C11 C10 120.17(17) . . . yes F6 C12 C13 120.56(16) . . . yes C11 C12 C13 121.42(17) . . . no F6 C12 C11 118.01(17) . . . yes C8 C13 C12 118.26(17) . . . no O3 C14 C8 115.36(16) . . . yes O4 C14 C8 120.75(17) . . . yes O3 C14 O4 123.90(18) . . . yes C8 C9 H9 122.3(12) . . . no C10 C9 H9 118.7(12) . . . no C8 C13 H13 121.9(13) . . . no C12 C13 H13 119.8(13) . . . no 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 C6 C1 C2 C3 0.5(3) . . . . no C7 C1 C2 C3 -176.99(17) . . . . no C2 C1 C6 C5 -1.0(3) . . . . no C7 C1 C6 C5 176.38(17) . . . . no C2 C1 C7 O1 174.75(16) . . . . no C2 C1 C7 O2 -4.6(3) . . . . no C6 C1 C7 O1 -2.7(3) . . . . no C6 C1 C7 O2 177.92(17) . . . . no C1 C2 C3 F1 178.86(16) . . . . no C1 C2 C3 C4 0.9(3) . . . . no F1 C3 C4 F2 -0.9(3) . . . . no F1 C3 C4 C5 -179.64(16) . . . . no C2 C3 C4 F2 177.20(17) . . . . no C2 C3 C4 C5 -1.6(3) . . . . no F2 C4 C5 F3 0.5(3) . . . . no F2 C4 C5 C6 -177.79(17) . . . . no C3 C4 C5 F3 179.30(16) . . . . no C3 C4 C5 C6 1.0(3) . . . . no F3 C5 C6 C1 -177.99(16) . . . . no C4 C5 C6 C1 0.3(3) . . . . no C13 C8 C9 C10 -0.1(3) . . . . no C14 C8 C9 C10 178.22(17) . . . . no C9 C8 C13 C12 -0.2(3) . . . . no C14 C8 C13 C12 -178.40(17) . . . . no C9 C8 C14 O3 -175.07(16) . . . . no C9 C8 C14 O4 4.6(3) . . . . no C13 C8 C14 O3 3.2(3) . . . . no C13 C8 C14 O4 -177.10(18) . . . . no C8 C9 C10 F4 179.74(16) . . . . no C8 C9 C10 C11 0.1(3) . . . . no F4 C10 C11 F5 0.5(3) . . . . no F4 C10 C11 C12 -179.54(16) . . . . no C9 C10 C11 F5 -179.90(16) . . . . no C9 C10 C11 C12 0.1(3) . . . . no F5 C11 C12 F6 0.2(3) . . . . no F5 C11 C12 C13 179.66(16) . . . . no C10 C11 C12 F6 -179.79(16) . . . . no C10 C11 C12 C13 -0.4(3) . . . . no F6 C12 C13 C8 179.81(16) . . . . no C11 C12 C13 C8 0.4(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 0.8400 1.7900 2.633(2) 175.00 2_467 yes O3 H3 O4 0.8400 1.7800 2.618(2) 177.00 2_756 yes C9 H9 F1 0.96(2) 2.47(2) 3.380(2) 158.8(14) 2_666 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; _iucr_refine_instructions_details ; ; data_datam10 _database_code_depnum_ccdc_archive 'CCDC 881267' #TrackingRef '11186_web_deposit_cif_file_9_RiteshDubey_1336563816.2345TeFBA.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H F4 O2, C7 H2 F4 O2' # 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 'C14 H3 F8 O4' _chemical_formula_iupac ? _chemical_formula_weight 387.16 _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 4.7350(6) _cell_length_b 5.9700(7) _cell_length_c 24.651(3) _cell_angle_alpha 84.773(6) _cell_angle_beta 87.020(6) _cell_angle_gamma 82.885(6) _cell_volume 688.00(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 6288 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.6 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 0.205 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9798 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' # number of measured reflections (redundant set) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_reflns_number 7297 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; _reflns_number_total 3149 # number of observed reflections (> n sig(I)) _reflns_number_gt 2387 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 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^)+(0.0592P)^2^+0.1545P] 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 3149 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.235 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.054 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F1A F Uani 0.4040(4) 0.6145(4) 0.44974(8) 0.549(3) 0.0475(8) . . F2 F Uani 0.4386(3) 0.9317(2) 0.37371(6) 1.000 0.0600(5) . . F3 F Uani 0.1379(3) 0.9545(2) 0.28281(6) 1.000 0.0656(5) . . F4 F Uani -0.2050(3) 0.6344(3) 0.27022(5) 1.000 0.0610(5) . . O1 O Uani 0.1980(3) 0.2366(3) 0.48744(6) 1.000 0.0517(5) . . O2 O Uani -0.1215(3) 0.1024(3) 0.43918(6) 1.000 0.0500(5) . . C1 C Uani 0.0770(4) 0.4292(3) 0.40249(7) 1.000 0.0351(5) . . C2 C Uani 0.2514(4) 0.5968(3) 0.40828(8) 1.000 0.0384(6) . . C3 C Uani 0.2708(4) 0.7701(3) 0.36789(9) 1.000 0.0420(6) . . C4 C Uani 0.1201(4) 0.7844(3) 0.32122(8) 1.000 0.0435(6) . . C5 C Uani -0.0528(4) 0.6186(4) 0.31518(8) 1.000 0.0425(6) . . C6 C Uani -0.0741(4) 0.4435(3) 0.35465(8) 1.000 0.0371(6) . . C7 C Uani 0.0454(4) 0.2423(3) 0.44539(8) 1.000 0.0372(6) . . F1B F Uani -0.2454(5) 0.3078(4) 0.34131(10) 0.451(3) 0.0416(8) . . F5 F Uani 1.2200(2) 0.29388(17) 0.07195(4) 1.000 0.0383(3) . . F6 F Uani 1.0614(2) 0.00639(17) 0.15294(5) 1.000 0.0446(4) . . F7 F Uani 0.6078(3) 0.1237(2) 0.22031(5) 1.000 0.0495(4) . . F8 F Uani 0.3133(2) 0.5410(2) 0.20693(5) 1.000 0.0442(4) . . O3 O Uani 1.1608(3) 0.7144(2) 0.02591(5) 1.000 0.0360(4) . . O4 O Uani 0.7609(3) 0.9384(2) 0.04613(5) 1.000 0.0374(4) . . C8 C Uani 0.8459(3) 0.5821(3) 0.09601(7) 1.000 0.0271(5) . . C9 C Uani 0.9956(3) 0.3656(3) 0.10380(7) 1.000 0.0282(5) . . C10 C Uani 0.9143(4) 0.2140(3) 0.14570(7) 1.000 0.0319(5) . . C11 C Uani 0.6855(4) 0.2721(3) 0.18029(7) 1.000 0.0329(5) . . C12 C Uani 0.5371(3) 0.4872(3) 0.17268(7) 1.000 0.0315(5) . . C13 C Uani 0.6147(4) 0.6391(3) 0.13141(7) 1.000 0.0300(5) . . C14 C Uani 0.9195(3) 0.7608(3) 0.05304(7) 1.000 0.0285(5) . . H1 H Uiso 0.17251 0.12467 0.50812 1.000 0.0775 . . H3 H Uiso 1.199(5) 0.836(5) 0.0011(12) 1.000 0.072(8) . . H13 H Uiso 0.500(4) 0.800(3) 0.1281(7) 1.000 0.022(4) . . 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 F1A 0.0471(13) 0.0570(14) 0.0434(12) -0.0105(10) -0.0096(10) -0.0181(10) F2 0.0468(7) 0.0496(7) 0.0892(10) -0.0207(7) 0.0103(7) -0.0228(6) F3 0.0629(9) 0.0594(8) 0.0674(9) 0.0156(7) 0.0151(7) -0.0022(7) F4 0.0516(8) 0.0892(10) 0.0419(7) -0.0090(7) -0.0091(6) -0.0015(7) O1 0.0551(9) 0.0575(10) 0.0458(8) -0.0020(7) -0.0074(7) -0.0197(8) O2 0.0513(9) 0.0543(9) 0.0491(8) -0.0083(7) -0.0004(7) -0.0226(7) C1 0.0290(9) 0.0399(10) 0.0376(9) -0.0133(8) 0.0054(8) -0.0048(7) C2 0.0295(9) 0.0459(11) 0.0427(10) -0.0188(9) 0.0031(8) -0.0064(8) C3 0.0306(9) 0.0394(10) 0.0588(12) -0.0199(10) 0.0103(9) -0.0089(8) C4 0.0357(10) 0.0446(11) 0.0475(11) -0.0057(9) 0.0134(9) 0.0007(8) C5 0.0317(10) 0.0590(12) 0.0367(10) -0.0142(9) 0.0027(8) 0.0001(9) C6 0.0288(9) 0.0449(10) 0.0401(10) -0.0178(9) 0.0035(8) -0.0063(8) C7 0.0305(9) 0.0446(11) 0.0387(10) -0.0155(8) 0.0050(8) -0.0072(8) F1B 0.0423(14) 0.0422(14) 0.0442(14) -0.0089(11) -0.0028(11) -0.0165(11) F5 0.0355(6) 0.0356(6) 0.0413(6) -0.0069(5) 0.0050(5) 0.0054(4) F6 0.0466(7) 0.0283(5) 0.0549(7) 0.0034(5) -0.0038(5) 0.0064(5) F7 0.0491(7) 0.0472(7) 0.0486(7) 0.0136(5) 0.0045(5) -0.0077(5) F8 0.0360(6) 0.0521(7) 0.0424(6) -0.0046(5) 0.0111(5) -0.0017(5) O3 0.0305(7) 0.0344(7) 0.0402(7) 0.0029(6) 0.0047(5) 0.0001(5) O4 0.0364(7) 0.0314(7) 0.0405(7) 0.0029(5) 0.0042(6) 0.0046(5) C8 0.0264(8) 0.0267(8) 0.0288(8) -0.0052(6) -0.0043(7) -0.0028(6) C9 0.0255(8) 0.0285(8) 0.0313(8) -0.0081(7) -0.0024(7) -0.0009(6) C10 0.0317(9) 0.0247(8) 0.0394(10) -0.0030(7) -0.0076(8) -0.0008(7) C11 0.0351(10) 0.0338(9) 0.0305(9) 0.0028(7) -0.0051(7) -0.0093(7) C12 0.0256(8) 0.0380(9) 0.0314(9) -0.0069(7) 0.0014(7) -0.0043(7) C13 0.0273(8) 0.0289(9) 0.0339(9) -0.0057(7) -0.0029(7) -0.0004(7) C14 0.0268(8) 0.0292(9) 0.0299(8) -0.0055(7) -0.0030(7) -0.0016(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C2 1.301(3) . . yes F1B C6 1.289(3) . . yes F2 C3 1.345(2) . . yes F3 C4 1.331(2) . . yes F4 C5 1.343(2) . . yes F5 C9 1.3381(19) . . yes F6 C10 1.346(2) . . yes F7 C11 1.333(2) . . yes F8 C12 1.3457(19) . . yes O1 C7 1.290(2) . . yes O2 C7 1.243(2) . . yes O1 H1 0.8200 . . no O3 C14 1.306(2) . . yes O4 C14 1.225(2) . . yes O3 H3 0.94(3) . . no C1 C7 1.482(3) . . no C1 C2 1.395(3) . . no C1 C6 1.402(3) . . no C2 C3 1.377(3) . . no C3 C4 1.376(3) . . no C4 C5 1.383(3) . . no C5 C6 1.371(3) . . no C8 C13 1.392(2) . . no C8 C14 1.493(2) . . no C8 C9 1.397(2) . . no C9 C10 1.382(2) . . no C10 C11 1.373(3) . . no C11 C12 1.387(3) . . no C12 C13 1.367(2) . . no C13 H13 1.042(18) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.00 . . . no C14 O3 H3 111.1(16) . . . no C2 C1 C7 122.00(16) . . . no C6 C1 C7 120.06(17) . . . no C2 C1 C6 117.94(16) . . . no F1A C2 C3 112.78(18) . . . yes C1 C2 C3 120.21(18) . . . no F1A C2 C1 127.00(19) . . . yes C2 C3 C4 121.61(17) . . . no F2 C3 C4 118.37(18) . . . yes F2 C3 C2 120.01(18) . . . yes F3 C4 C3 121.00(17) . . . yes F3 C4 C5 120.53(18) . . . yes C3 C4 C5 118.47(18) . . . no F4 C5 C6 120.29(19) . . . yes C4 C5 C6 121.00(18) . . . no F4 C5 C4 118.70(19) . . . yes F1B C6 C5 111.4(2) . . . yes C1 C6 C5 120.77(17) . . . no F1B C6 C1 127.86(19) . . . yes O2 C7 C1 119.46(17) . . . yes O1 C7 O2 124.13(18) . . . yes O1 C7 C1 116.41(17) . . . yes C9 C8 C13 118.19(16) . . . no C13 C8 C14 117.03(15) . . . no C9 C8 C14 124.77(14) . . . no F5 C9 C8 122.87(15) . . . yes C8 C9 C10 120.31(15) . . . no F5 C9 C10 116.81(15) . . . yes F6 C10 C11 119.35(16) . . . yes C9 C10 C11 120.95(16) . . . no F6 C10 C9 119.70(16) . . . yes F7 C11 C12 120.82(16) . . . yes C10 C11 C12 118.79(16) . . . no F7 C11 C10 120.39(16) . . . yes F8 C12 C13 121.07(16) . . . yes C11 C12 C13 120.98(16) . . . no F8 C12 C11 117.95(15) . . . yes C8 C13 C12 120.78(16) . . . no O3 C14 C8 115.41(14) . . . yes O4 C14 C8 120.05(14) . . . yes O3 C14 O4 124.51(16) . . . yes C8 C13 H13 121.2(10) . . . no C12 C13 H13 118.0(10) . . . no 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 C6 C1 C2 F1A 178.9(2) . . . . no C6 C1 C2 C3 0.3(3) . . . . no C7 C1 C2 F1A -0.1(3) . . . . no C7 C1 C2 C3 -178.77(18) . . . . no C2 C1 C6 C5 -0.7(3) . . . . no C7 C1 C6 C5 178.33(18) . . . . no C2 C1 C7 O1 -3.1(3) . . . . no C2 C1 C7 O2 177.12(18) . . . . no C6 C1 C7 O1 177.91(17) . . . . no C6 C1 C7 O2 -1.9(3) . . . . no F1A C2 C3 F2 1.0(3) . . . . no F1A C2 C3 C4 -178.53(19) . . . . no C1 C2 C3 F2 179.81(17) . . . . no C1 C2 C3 C4 0.3(3) . . . . no F2 C3 C4 F3 -0.4(3) . . . . no F2 C3 C4 C5 -179.92(19) . . . . no C2 C3 C4 F3 179.10(18) . . . . no C2 C3 C4 C5 -0.4(3) . . . . no F3 C4 C5 F4 -0.9(3) . . . . no F3 C4 C5 C6 -179.57(18) . . . . no C3 C4 C5 F4 178.61(18) . . . . no C3 C4 C5 C6 -0.1(3) . . . . no F4 C5 C6 C1 -178.02(18) . . . . no C4 C5 C6 C1 0.6(3) . . . . no C13 C8 C9 F5 179.75(15) . . . . no C13 C8 C9 C10 -0.1(2) . . . . no C14 C8 C9 F5 -1.8(3) . . . . no C14 C8 C9 C10 178.39(16) . . . . no C9 C8 C13 C12 0.1(3) . . . . no C14 C8 C13 C12 -178.48(15) . . . . no C9 C8 C14 O3 -8.3(2) . . . . no C9 C8 C14 O4 173.36(16) . . . . no C13 C8 C14 O3 170.16(15) . . . . no C13 C8 C14 O4 -8.2(2) . . . . no F5 C9 C10 F6 0.5(2) . . . . no F5 C9 C10 C11 -179.63(16) . . . . no C8 C9 C10 F6 -179.62(15) . . . . no C8 C9 C10 C11 0.2(3) . . . . no F6 C10 C11 F7 -0.7(3) . . . . no F6 C10 C11 C12 179.47(15) . . . . no C9 C10 C11 F7 179.48(16) . . . . no C9 C10 C11 C12 -0.4(3) . . . . no F7 C11 C12 F8 0.1(3) . . . . no F7 C11 C12 C13 -179.44(16) . . . . no C10 C11 C12 F8 179.92(16) . . . . no C10 C11 C12 C13 0.4(3) . . . . no F8 C12 C13 C8 -179.79(15) . . . . no C11 C12 C13 C8 -0.3(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F1A F2 2.554(3) . . no F1A O1 2.641(3) . . no F1A F1A 2.854(3) . 2_666 no F1A O1 2.777(3) . 2_666 no F1A C7 3.365(3) . 2_566 no F1B F2 2.881(3) . 1_445 no F1B F3 3.026(3) . 1_545 no F1B F4 2.519(3) . . no F1B O2 2.664(3) . . no F1B C2 3.236(3) . 1_455 no F2 C5 3.223(3) . 1_655 no F2 C7 3.070(2) . 1_565 no F2 F1A 2.554(3) . . no F2 F3 2.701(2) . . no F2 O2 3.140(2) . 1_565 no F2 O2 3.026(2) . 1_665 no F2 C1 3.355(2) . 1_565 no F2 F1B 2.881(3) . 1_665 no F3 F2 2.701(2) . . no F3 F4 2.704(2) . . no F3 F1B 3.026(3) . 1_565 no F3 F7 2.874(2) . 1_565 no F3 F7 3.031(2) . 1_465 no F4 F7 3.106(2) . 1_465 no F4 F3 2.704(2) . . no F4 F8 2.8617(18) . . no F4 C11 3.337(2) . 1_455 no F4 F8 2.9649(18) . 1_455 no F4 F1B 2.519(3) . . no F4 C12 3.000(2) . 1_455 no F5 O3 2.6474(16) . . no F5 F6 2.6523(15) . . no F5 O3 3.0934(17) . 2_765 no F5 C14 3.238(2) . 2_765 no F5 C12 3.330(2) . 1_655 no F6 O4 3.1383(18) . 1_545 no F6 C8 3.296(2) . 1_545 no F6 F5 2.6523(15) . . no F6 F7 2.7074(17) . . no F6 F8 3.0958(16) . 1_645 no F6 C13 3.255(2) . 1_645 no F6 C14 3.121(2) . 1_545 no F6 C13 3.323(2) . 1_545 no F7 F3 3.031(2) . 1_645 no F7 F4 3.106(2) . 1_645 no F7 F3 2.874(2) . 1_545 no F7 F8 2.7014(17) . . no F7 F6 2.7074(17) . . no F8 F4 2.9649(18) . 1_655 no F8 C5 3.144(2) . . no F8 C9 3.331(2) . 1_455 no F8 F4 2.8617(18) . . no F8 C4 3.322(2) . . no F8 F6 3.0958(16) . 1_465 no F8 F7 2.7014(17) . . no F6 H13 2.362(19) . 1_645 no O1 F1A 2.777(3) . 2_666 no O1 F1A 2.641(3) . . no O1 O2 2.636(2) . 2_556 no O1 C2 3.391(2) . 2_566 no O2 F2 3.026(2) . 1_445 no O2 F2 3.140(2) . 1_545 no O2 C3 3.140(3) . 1_545 no O2 F1B 2.664(3) . . no O2 O1 2.636(2) . 2_556 no O2 C7 3.364(3) . 2_556 no O3 O4 2.6531(18) . 2_775 no O3 F5 2.6474(16) . . no O3 F5 3.0934(17) . 2_765 no O3 C9 3.408(2) . 2_765 no O4 O4 3.2269(19) . 2_775 no O4 F6 3.1383(18) . 1_565 no O4 C9 3.360(2) . 1_565 no O4 C10 3.237(2) . 1_565 no O4 C14 3.314(2) . 2_775 no O4 O3 2.6531(18) . 2_775 no O2 H1 1.8200 . 2_556 no O4 H13 2.446(18) . . no O4 H3 1.72(3) . 2_775 no C1 F2 3.355(2) . 1_545 no C2 O1 3.391(2) . 2_566 no C2 C6 3.441(3) . 1_655 no C2 F1B 3.236(3) . 1_655 no C3 C5 3.439(3) . 1_655 no C3 C6 3.470(3) . 1_655 no C3 O2 3.140(3) . 1_565 no C3 C7 3.572(3) . 1_565 no C4 F8 3.322(2) . . no C5 F2 3.223(3) . 1_455 no C5 C3 3.439(3) . 1_455 no C5 F8 3.144(2) . . no C6 C2 3.441(3) . 1_455 no C6 C3 3.470(3) . 1_455 no C7 F2 3.070(2) . 1_545 no C7 C3 3.572(3) . 1_545 no C7 F1A 3.365(3) . 2_566 no C7 O2 3.364(3) . 2_556 no C8 F6 3.296(2) . 1_565 no C9 F8 3.331(2) . 1_655 no C9 O4 3.360(2) . 1_545 no C9 C12 3.335(2) . 1_655 no C9 O3 3.408(2) . 2_765 no C10 O4 3.237(2) . 1_545 no C11 F4 3.337(2) . 1_655 no C12 F4 3.000(2) . 1_655 no C12 F5 3.330(2) . 1_455 no C12 C9 3.335(2) . 1_455 no C13 F6 3.255(2) . 1_465 no C13 F6 3.323(2) . 1_565 no C14 O4 3.314(2) . 2_775 no C14 F6 3.121(2) . 1_565 no C14 F5 3.238(2) . 2_765 no C7 H1 2.6800 . 2_556 no C14 H3 2.66(3) . 2_775 no H1 H1 2.4100 . 2_556 no H1 C7 2.6800 . 2_556 no H1 O2 1.8200 . 2_556 no H3 O4 1.72(3) . 2_775 no H3 C14 2.66(3) . 2_775 no H3 H3 2.54(4) . 2_775 no H13 F6 2.362(19) . 1_465 no H13 O4 2.446(18) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 0.8200 1.8200 2.636(2) 173.00 2_556 yes O3 H3 O4 0.94(3) 1.72(3) 2.6531(18) 175(2) 2_775 yes C13 H13 F6 1.042(18) 2.362(19) 3.255(2) 143.1(14) 1_465 yes data_24_ss _database_code_depnum_ccdc_archive 'CCDC 881268' #TrackingRef '11187_web_deposit_cif_file_10_RiteshDubey_1336563816.24SS.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 F O2' # 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 'C7 H4 F O2' _chemical_formula_iupac ? _chemical_formula_weight 139.10 _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 C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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 5.0609(10) _cell_length_b 5.3645(11) _cell_length_c 22.703(5) _cell_angle_alpha 90 _cell_angle_beta 95.007(7) _cell_angle_gamma 90 _cell_volume 614.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5051 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 27.7 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.120 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.130 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.985 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 # number of measured reflections (redundant set) _diffrn_reflns_number 5762 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _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 1408 # number of observed reflections (> n sig(I)) _reflns_number_gt 1090 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0597P)^2^+0.3897P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1408 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.208 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F2 F Uani 0.5411(4) 0.2055(5) 0.22301(9) 0.620 0.0472(8) d P . . O1 O Uani 1.3897(3) 0.6312(3) 0.06394(6) 1.000 0.0364(5) d . . . O2 O Uani 1.2597(3) 0.2906(3) 0.01256(6) 1.000 0.0363(5) d . . . C1 C Uani 1.0601(4) 0.3768(4) 0.10098(8) 1.000 0.0267(5) d . . . C2 C Uani 1.0475(4) 0.5222(4) 0.15149(9) 1.000 0.0302(6) d . . . C3 C Uani 0.8699(4) 0.4646(5) 0.19263(9) 1.000 0.0345(7) d . . . C4 C Uani 0.7084(4) 0.2605(4) 0.18293(9) 1.000 0.0338(7) d . . . C5 C Uani 0.7163(4) 0.1110(4) 0.13385(10) 1.000 0.0352(7) d . . . C6 C Uani 0.8943(4) 0.1699(4) 0.09247(9) 1.000 0.0322(6) d . . . C7 C Uani 1.2470(4) 0.4345(4) 0.05608(8) 1.000 0.0276(6) d . . . F1 F Uani 1.2045(6) 0.7133(7) 0.16511(14) 0.380 0.0374(10) d P . . H1 H Uiso 1.48760 0.64560 0.03610 1.000 0.0550 c R . . H5 H Uiso 0.601(5) -0.038(5) 0.1280(10) 1.000 0.039(6) d . . . H6 H Uiso 0.904(4) 0.070(4) 0.0555(10) 1.000 0.031(6) d . . . H3 H Uiso 0.854(5) 0.569(5) 0.2264(11) 1.000 0.045(7) d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0416(12) 0.0608(15) 0.0421(12) 0.0095(11) 0.0201(9) -0.0055(11) O1 0.0384(9) 0.0378(9) 0.0347(8) -0.0040(7) 0.0132(6) -0.0130(7) O2 0.0388(9) 0.0418(9) 0.0296(8) -0.0090(7) 0.0101(6) -0.0090(7) C1 0.0252(9) 0.0288(10) 0.0263(9) 0.0023(8) 0.0040(7) 0.0003(8) C2 0.0277(10) 0.0334(11) 0.0297(10) -0.0017(9) 0.0043(8) -0.0019(8) C3 0.0338(11) 0.0423(13) 0.0278(10) -0.0034(9) 0.0058(8) 0.0015(10) C4 0.0276(10) 0.0421(13) 0.0325(11) 0.0087(9) 0.0073(8) 0.0018(9) C5 0.0338(11) 0.0320(12) 0.0406(12) 0.0050(10) 0.0077(9) -0.0070(9) C6 0.0329(11) 0.0326(11) 0.0319(11) -0.0007(9) 0.0075(8) -0.0027(9) C7 0.0269(10) 0.0293(10) 0.0267(10) 0.0003(8) 0.0026(7) -0.0021(8) F1 0.0389(18) 0.0431(19) 0.0317(16) -0.0106(15) 0.0123(13) -0.0106(15) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.317(4) . . yes F2 C4 1.329(3) . . yes O1 C7 1.282(3) . . yes O2 C7 1.260(2) . . yes O1 H1 0.8400 . . no C1 C7 1.483(3) . . no C1 C2 1.393(3) . . no C1 C6 1.395(3) . . no C2 C3 1.387(3) . . no C3 C4 1.373(3) . . no C4 C5 1.376(3) . . no C5 C6 1.393(3) . . no C3 H3 0.96(3) . . no C5 H5 0.99(3) . . no C6 H6 1.00(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.00 . . . no C2 C1 C7 121.80(19) . . . no C6 C1 C7 118.89(18) . . . no C2 C1 C6 119.31(18) . . . no C1 C2 C3 120.6(2) . . . no F1 C2 C1 124.0(2) . . . yes F1 C2 C3 115.4(2) . . . yes C2 C3 C4 118.8(2) . . . no F2 C4 C3 118.3(2) . . . yes C3 C4 C5 122.40(19) . . . no F2 C4 C5 119.4(2) . . . yes C4 C5 C6 118.68(19) . . . no C1 C6 C5 120.24(19) . . . no O1 C7 C1 117.48(17) . . . yes O2 C7 C1 119.38(19) . . . yes O1 C7 O2 123.14(18) . . . yes C2 C3 H3 120.9(16) . . . no C4 C3 H3 120.3(15) . . . no C4 C5 H5 121.3(14) . . . no C6 C5 H5 120.0(14) . . . no C1 C6 H6 118.0(12) . . . no C5 C6 H6 121.7(12) . . . no 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 C6 C1 C2 C3 -0.9(3) . . . . no C7 C1 C2 C3 179.7(2) . . . . no C2 C1 C6 C5 0.6(3) . . . . no C7 C1 C6 C5 -179.9(2) . . . . no C2 C1 C7 O1 -3.2(3) . . . . no C2 C1 C7 O2 176.66(19) . . . . no C6 C1 C7 O1 177.39(19) . . . . no C6 C1 C7 O2 -2.8(3) . . . . no C1 C2 C3 C4 0.6(3) . . . . no C2 C3 C4 F2 179.2(2) . . . . no C2 C3 C4 C5 0.0(3) . . . . no F2 C4 C5 C6 -179.5(2) . . . . no C3 C4 C5 C6 -0.2(3) . . . . no C4 C5 C6 C1 -0.1(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 0.8400 1.7900 2.623(2) 168.00 3_865 yes C3 H3 F2 0.96(3) 2.50(3) 3.219(3) 132(2) 2_655 yes C5 H5 O1 0.99(3) 2.48(3) 3.379(3) 151.0(18) 1_445 yes C6 H6 O2 1.00(2) 2.57(2) 3.474(3) 150.6(16) 3_755 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; _iucr_refine_instructions_details ; ; #===END