data_i14220 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H26 O5 S' _chemical_formula_sum 'C27 H26 O5 S' _chemical_formula_weight 462.54 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 4.65980(10) _cell_length_b 11.2839(3) _cell_length_c 12.0321(3) _cell_angle_alpha 115.307(2) _cell_angle_beta 97.601(2) _cell_angle_gamma 94.255(2) _cell_volume 560.85(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 7518 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 31.49 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description niddle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method ? _exptl_crystal_F_000 244 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.9474 _exptl_absorpt_correction_T_max 0.968 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_number 10062 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.904 _diffrn_reflns_theta_max 27.097 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 1 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1 _diffrn_reflns_point_group_measured_fraction_full 0.714 _diffrn_reflns_point_group_measured_fraction_max 0.692 _reflns_number_total 3396 _reflns_number_gt 3188 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+0.1766P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3396 _refine_ls_number_parameters 299 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details ; Flack x determined using 847 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.07(4) _refine_diff_density_max 0.227 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group S S 0.02859(11) 0.72699(6) 0.44237(5) 0.01751(14) Uani 1 d . . O2 O -0.1567(3) 0.84830(16) 0.78183(15) 0.0148(4) Uani 1 d . . O3 O 0.2170(3) 0.77669(15) 0.86817(14) 0.0127(3) Uani 1 d . . O4 O 0.2014(3) 0.47962(16) 0.70746(15) 0.0131(3) Uani 1 d . . O5 O -0.3113(3) 0.59268(15) 0.53090(14) 0.0130(3) Uani 1 d . . O6 O -0.0431(3) 0.29578(16) 0.52645(15) 0.0163(4) Uani 1 d . . C1 C -0.1778(5) 0.7219(2) 0.5602(2) 0.0129(5) Uani 1 d . . H1 H -0.3389 0.7762 0.5622 0.015 Uiso 1 calc . . C2 C 0.0221(5) 0.7907(2) 0.6891(2) 0.0132(5) Uani 1 d . . H2 H 0.167 0.8619 0.6912 0.016 Uiso 1 calc . . C3 C 0.1826(5) 0.7016(2) 0.7348(2) 0.0126(5) Uani 1 d . . H3 H 0.379 0.6947 0.7095 0.015 Uiso 1 calc . . C4 C 0.0122(5) 0.5653(2) 0.6864(2) 0.0124(5) Uani 1 d . . H4 H -0.1561 0.5698 0.731 0.015 Uiso 1 calc . . C5 C -0.1010(5) 0.5126(2) 0.5473(2) 0.0130(4) Uani 1 d . . H5 H 0.0642 0.5171 0.5033 0.016 Uiso 1 calc . . C6 C -0.2485(5) 0.3707(2) 0.4955(2) 0.0158(5) Uani 1 d . . H6A H -0.4248 0.3674 0.5325 0.019 Uiso 1 calc . . H6B H -0.3094 0.333 0.4037 0.019 Uiso 1 calc . . C7 C 0.0471(5) 0.3481(2) 0.6570(2) 0.0140(5) Uani 1 d . . H7 H -0.1281 0.3492 0.697 0.017 Uiso 1 calc . . C8 C 0.2518(5) 0.2646(2) 0.6875(2) 0.0149(5) Uani 1 d . . C9 C 0.3818(5) 0.3066(2) 0.8110(2) 0.0188(5) Uani 1 d . . H9 H 0.3428 0.3871 0.8737 0.023 Uiso 1 calc . . C10 C 0.5696(5) 0.2316(3) 0.8438(2) 0.0219(6) Uani 1 d . . H10 H 0.6565 0.2604 0.9288 0.026 Uiso 1 calc . . C11 C 0.6292(6) 0.1150(3) 0.7522(3) 0.0240(6) Uani 1 d . . H11 H 0.7584 0.064 0.7741 0.029 Uiso 1 calc . . C12 C 0.5004(6) 0.0733(3) 0.6295(3) 0.0250(6) Uani 1 d . . H12 H 0.5417 -0.0067 0.5669 0.03 Uiso 1 calc . . C13 C 0.3100(5) 0.1470(2) 0.5955(2) 0.0194(5) Uani 1 d . . H13 H 0.2211 0.1171 0.5106 0.023 Uiso 1 calc . . C14 C -0.0490(5) 0.8303(2) 0.8899(2) 0.0129(5) Uani 1 d . . H14 H -0.1934 0.7662 0.8987 0.015 Uiso 1 calc . . C15 C 0.0114(5) 0.9589(2) 1.0071(2) 0.0146(5) Uani 1 d . . C16 C 0.2071(6) 1.0636(2) 1.0176(2) 0.0217(5) Uani 1 d . . H16 H 0.3024 1.0549 0.95 0.026 Uiso 1 calc . . C17 C 0.2628(6) 1.1805(3) 1.1269(3) 0.0283(6) Uani 1 d . . H17 H 0.3952 1.2526 1.1339 0.034 Uiso 1 calc . . C18 C 0.1260(6) 1.1933(3) 1.2267(3) 0.0295(7) Uani 1 d . . H18 H 0.166 1.2735 1.3018 0.035 Uiso 1 calc . . C19 C -0.0668(6) 1.0895(3) 1.2163(3) 0.0275(6) Uani 1 d . . H19 H -0.1598 1.0979 1.2844 0.033 Uiso 1 calc . . C20 C -0.1268(6) 0.9716(3) 1.1060(2) 0.0208(5) Uani 1 d . . H20 H -0.262 0.9002 1.0986 0.025 Uiso 1 calc . . C21 C -0.2721(5) 0.6875(2) 0.3192(2) 0.0154(5) Uani 1 d . . C22 C -0.4040(5) 0.5572(2) 0.2469(2) 0.0172(5) Uani 1 d . . H22 H -0.3299 0.4879 0.2614 0.021 Uiso 1 calc . . C23 C -0.6449(5) 0.5283(2) 0.1531(2) 0.0184(5) Uani 1 d . . H23 H -0.737 0.4391 0.1056 0.022 Uiso 1 calc . . C24 C -0.7535(5) 0.6271(3) 0.1275(2) 0.0157(5) Uani 1 d . . C25 C -0.6164(5) 0.7570(3) 0.2001(2) 0.0178(5) Uani 1 d . . H25 H -0.6876 0.8262 0.1844 0.021 Uiso 1 calc . . C26 C -0.3787(5) 0.7874(3) 0.2947(2) 0.0164(5) Uani 1 d . . H26 H -0.2881 0.8767 0.3429 0.02 Uiso 1 calc . . C27 C -1.0087(5) 0.5945(3) 0.0235(2) 0.0204(5) Uani 1 d . . H27A H -0.9407 0.6073 -0.0448 0.031 Uiso 1 calc . . H27B H -1.1545 0.6529 0.0549 0.031 Uiso 1 calc . . H27C H -1.0971 0.502 -0.0074 0.031 Uiso 1 calc . . 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 S 0.0138(3) 0.0272(3) 0.0139(3) 0.0118(3) 0.0022(2) 0.0004(2) O2 0.0169(9) 0.0165(9) 0.0121(8) 0.0063(7) 0.0043(7) 0.0069(7) O3 0.0120(8) 0.0138(8) 0.0103(7) 0.0036(6) 0.0006(6) 0.0036(6) O4 0.0123(8) 0.0116(8) 0.0141(8) 0.0047(7) 0.0003(6) 0.0032(6) O5 0.0107(8) 0.0148(8) 0.0133(8) 0.0064(7) 0.0009(6) 0.0023(7) O6 0.0178(8) 0.0152(8) 0.0130(8) 0.0037(7) 0.0014(7) 0.0048(7) C1 0.0131(11) 0.0155(12) 0.0106(11) 0.0059(9) 0.0032(9) 0.0021(9) C2 0.0129(11) 0.0137(11) 0.0131(11) 0.0055(9) 0.0048(9) 0.0024(9) C3 0.0119(11) 0.0148(12) 0.0101(10) 0.0045(9) 0.0024(9) 0.0023(9) C4 0.0119(11) 0.0152(11) 0.0116(10) 0.0067(9) 0.0030(9) 0.0046(9) C5 0.0116(10) 0.0161(12) 0.0115(10) 0.0060(9) 0.0024(8) 0.0041(9) C6 0.0143(11) 0.0173(12) 0.0142(11) 0.0063(10) -0.0005(9) 0.0032(10) C7 0.0144(11) 0.0121(11) 0.0138(11) 0.0044(9) 0.0023(9) 0.0017(9) C8 0.0123(11) 0.0140(11) 0.0202(12) 0.0090(10) 0.0045(9) -0.0003(9) C9 0.0197(12) 0.0179(13) 0.0206(13) 0.0090(10) 0.0061(10) 0.0047(10) C10 0.0207(13) 0.0233(13) 0.0247(14) 0.0148(11) 0.0010(11) 0.0005(11) C11 0.0212(13) 0.0186(13) 0.0382(16) 0.0183(12) 0.0039(12) 0.0050(11) C12 0.0273(14) 0.0138(13) 0.0320(15) 0.0072(12) 0.0075(12) 0.0063(11) C13 0.0214(13) 0.0134(12) 0.0209(13) 0.0055(10) 0.0034(10) 0.0013(10) C14 0.0130(11) 0.0143(11) 0.0120(11) 0.0061(9) 0.0028(9) 0.0028(9) C15 0.0138(11) 0.0163(12) 0.0131(11) 0.0064(10) -0.0010(9) 0.0058(9) C16 0.0236(13) 0.0176(13) 0.0220(13) 0.0074(11) 0.0025(11) 0.0023(11) C17 0.0257(14) 0.0173(14) 0.0338(16) 0.0061(12) -0.0023(12) 0.0015(12) C18 0.0267(15) 0.0253(15) 0.0204(14) -0.0033(12) -0.0051(11) 0.0114(12) C19 0.0296(15) 0.0313(16) 0.0167(13) 0.0045(12) 0.0055(11) 0.0117(13) C20 0.0233(13) 0.0216(13) 0.0167(12) 0.0072(11) 0.0046(10) 0.0057(11) C21 0.0132(11) 0.0255(13) 0.0090(10) 0.0093(10) 0.0019(9) 0.0017(10) C22 0.0214(13) 0.0179(12) 0.0150(11) 0.0090(10) 0.0047(10) 0.0064(10) C23 0.0201(12) 0.0201(13) 0.0134(11) 0.0069(10) 0.0012(10) -0.0001(10) C24 0.0148(11) 0.0245(14) 0.0129(11) 0.0112(10) 0.0070(10) 0.0060(10) C25 0.0189(12) 0.0209(13) 0.0193(12) 0.0125(11) 0.0069(10) 0.0072(10) C26 0.0177(12) 0.0159(12) 0.0162(12) 0.0073(10) 0.0054(10) 0.0010(10) C27 0.0192(13) 0.0266(14) 0.0162(12) 0.0107(11) 0.0015(10) 0.0039(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S C21 1.776(2) . ? S C1 1.833(2) . ? O2 C14 1.432(3) . ? O2 C2 1.438(3) . ? O3 C14 1.425(3) . ? O3 C3 1.438(3) . ? O4 C7 1.430(3) . ? O4 C4 1.433(3) . ? O5 C1 1.416(3) . ? O5 C5 1.431(3) . ? O6 C7 1.410(3) . ? O6 C6 1.437(3) . ? C1 C2 1.535(3) . ? C1 H1 1 . ? C2 C3 1.532(3) . ? C2 H2 1 . ? C3 C4 1.506(3) . ? C3 H3 1 . ? C4 C5 1.517(3) . ? C4 H4 1 . ? C5 C6 1.515(3) . ? C5 H5 1 . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.506(3) . ? C7 H7 1 . ? C8 C9 1.384(3) . ? C8 C13 1.391(3) . ? C9 C10 1.394(3) . ? C9 H9 0.95 . ? C10 C11 1.385(4) . ? C10 H10 0.95 . ? C11 C12 1.376(4) . ? C11 H11 0.95 . ? C12 C13 1.396(3) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 C15 1.503(3) . ? C14 H14 1 . ? C15 C20 1.386(3) . ? C15 C16 1.387(3) . ? C16 C17 1.383(4) . ? C16 H16 0.95 . ? C17 C18 1.391(4) . ? C17 H17 0.95 . ? C18 C19 1.372(4) . ? C18 H18 0.95 . ? C19 C20 1.395(4) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 C22 1.388(3) . ? C21 C26 1.390(3) . ? C22 C23 1.391(3) . ? C22 H22 0.95 . ? C23 C24 1.389(3) . ? C23 H23 0.95 . ? C24 C25 1.393(4) . ? C24 C27 1.505(3) . ? C25 C26 1.384(3) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 S C1 98.10(11) . . ? C14 O2 C2 108.93(16) . . ? C14 O3 C3 105.60(16) . . ? C7 O4 C4 109.89(16) . . ? C1 O5 C5 111.79(16) . . ? C7 O6 C6 111.01(17) . . ? O5 C1 C2 113.49(19) . . ? O5 C1 S 113.18(15) . . ? C2 C1 S 108.82(15) . . ? O5 C1 H1 107 . . ? C2 C1 H1 107 . . ? S C1 H1 107 . . ? O2 C2 C3 102.71(17) . . ? O2 C2 C1 108.32(18) . . ? C3 C2 C1 116.74(19) . . ? O2 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? C1 C2 H2 109.6 . . ? O3 C3 C4 113.08(18) . . ? O3 C3 C2 101.41(16) . . ? C4 C3 C2 112.57(18) . . ? O3 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? O4 C4 C3 109.04(17) . . ? O4 C4 C5 109.55(17) . . ? C3 C4 C5 109.11(17) . . ? O4 C4 H4 109.7 . . ? C3 C4 H4 109.7 . . ? C5 C4 H4 109.7 . . ? O5 C5 C6 109.23(18) . . ? O5 C5 C4 107.88(17) . . ? C6 C5 C4 109.42(18) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 108.10(18) . . ? O6 C6 H6A 110.1 . . ? C5 C6 H6A 110.1 . . ? O6 C6 H6B 110.1 . . ? C5 C6 H6B 110.1 . . ? H6A C6 H6B 108.4 . . ? O6 C7 O4 110.99(18) . . ? O6 C7 C8 110.11(18) . . ? O4 C7 C8 107.41(18) . . ? O6 C7 H7 109.4 . . ? O4 C7 H7 109.4 . . ? C8 C7 H7 109.4 . . ? C9 C8 C13 119.8(2) . . ? C9 C8 C7 118.4(2) . . ? C13 C8 C7 121.8(2) . . ? C8 C9 C10 120.4(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 119.8(2) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 119.7(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 121.0(2) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C8 C13 C12 119.3(2) . . ? C8 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? O3 C14 O2 106.06(16) . . ? O3 C14 C15 109.45(18) . . ? O2 C14 C15 111.95(18) . . ? O3 C14 H14 109.8 . . ? O2 C14 H14 109.8 . . ? C15 C14 H14 109.8 . . ? C20 C15 C16 120.0(2) . . ? C20 C15 C14 119.4(2) . . ? C16 C15 C14 120.6(2) . . ? C17 C16 C15 119.7(2) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 119.8(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 119.8(3) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C26 119.3(2) . . ? C22 C21 S 120.57(18) . . ? C26 C21 S 120.10(19) . . ? C21 C22 C23 119.9(2) . . ? C21 C22 H22 120 . . ? C23 C22 H22 120 . . ? C24 C23 C22 121.3(2) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C23 C24 C25 117.9(2) . . ? C23 C24 C27 121.0(2) . . ? C25 C24 C27 121.0(2) . . ? C26 C25 C24 121.3(2) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 C26 C21 120.1(2) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF