# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Friscic, Tomislav' _publ_contact_author_email tomislav.friscic@mcgill.ca _publ_author_name 'Tomislav Friscic' data_(mdppo)2(tfib) _database_code_depnum_ccdc_archive 'CCDC 819334' #TrackingRef '- deposit_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; methyldiphenylphosphine:1,4-diiodotetrafluorobenzene 2/1 ; _chemical_name_common 'methyldiphenylphosphine:1,4-diiodotetrafluorobenzene 2/1' _chemical_melting_point ? _chemical_formula_moiety '2(C13 H13 P O) (C6 F4 I2)' _chemical_formula_sum 'C32 H26 F4 I2 O2 P2' _chemical_formula_weight 834.27 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 5.74470(10) _cell_length_b 16.4119(2) _cell_length_c 32.2290(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3038.60(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 23791 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 2.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 17114 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3408 _reflns_number_gt 2744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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. All non-hydrogen atoms have been refined anisotropically and hydrogen atoms have been placed in positions calculated on the basis of the hybridisation state of the belonging carbon atom. ; _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^)+(0.0237P)^2^+2.5177P] 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 3408 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0657 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.19161(4) 0.975779(12) 0.407760(6) 0.03661(8) Uani 1 1 d . . . P1 P -0.16162(11) 1.21664(4) 0.32127(2) 0.02137(15) Uani 1 1 d . . . F1 F 0.6464(3) 1.07819(11) 0.43060(5) 0.0388(4) Uani 1 1 d . . . F2 F 0.1090(3) 0.90744(10) 0.49954(5) 0.0391(4) Uani 1 1 d . . . O1 O -0.4118(3) 1.23418(11) 0.31353(6) 0.0283(4) Uani 1 1 d . . . C1 C 0.3732(5) 0.99139(17) 0.46300(9) 0.0260(6) Uani 1 1 d . . . C2 C 0.5722(5) 1.03856(16) 0.46458(9) 0.0274(6) Uani 1 1 d . . . C3 C 0.3030(5) 0.95349(16) 0.49905(9) 0.0272(6) Uani 1 1 d . . . C4 C 0.0358(5) 1.27272(16) 0.28938(8) 0.0278(6) Uani 1 1 d . . . H4A H 0.0209 1.2545 0.2605 0.042 Uiso 1 1 calc R . . H4B H 0.1955 1.2635 0.2990 0.042 Uiso 1 1 calc R . . H4C H -0.0008 1.3309 0.2911 0.042 Uiso 1 1 calc R . . C5 C -0.0834(5) 1.23964(15) 0.37430(8) 0.0227(6) Uani 1 1 d . . . C6 C 0.1288(5) 1.21438(18) 0.39133(9) 0.0284(6) Uani 1 1 d . . . H6 H 0.2387 1.1864 0.3745 0.034 Uiso 1 1 calc R . . C7 C 0.1791(5) 1.23013(18) 0.43261(9) 0.0332(7) Uani 1 1 d . . . H7 H 0.3222 1.2121 0.4442 0.040 Uiso 1 1 calc R . . C8 C 0.0214(5) 1.27192(16) 0.45691(9) 0.0329(7) Uani 1 1 d . . . H8 H 0.0565 1.2828 0.4852 0.039 Uiso 1 1 calc R . . C9 C -0.1869(5) 1.29787(18) 0.44026(9) 0.0339(7) Uani 1 1 d . . . H9 H -0.2944 1.3271 0.4570 0.041 Uiso 1 1 calc R . . C10 C -0.2395(5) 1.28130(17) 0.39904(9) 0.0293(6) Uani 1 1 d . . . H10 H -0.3839 1.2988 0.3878 0.035 Uiso 1 1 calc R . . C11 C -0.0937(5) 1.11012(16) 0.31436(8) 0.0224(6) Uani 1 1 d . . . C12 C -0.2522(5) 1.05384(18) 0.33026(9) 0.0277(6) Uani 1 1 d . . . H12 H -0.3901 1.0727 0.3434 0.033 Uiso 1 1 calc R . . C13 C -0.2115(5) 0.97113(18) 0.32715(9) 0.0328(7) Uani 1 1 d . . . H13 H -0.3199 0.9335 0.3385 0.039 Uiso 1 1 calc R . . C14 C -0.0129(5) 0.94321(18) 0.30754(9) 0.0329(7) Uani 1 1 d . . . H14 H 0.0145 0.8863 0.3052 0.039 Uiso 1 1 calc R . . C15 C 0.1466(5) 0.99818(18) 0.29132(10) 0.0324(7) Uani 1 1 d . . . H15 H 0.2824 0.9789 0.2777 0.039 Uiso 1 1 calc R . . C16 C 0.1075(5) 1.08128(17) 0.29505(9) 0.0292(6) Uani 1 1 d . . . H16 H 0.2184 1.1188 0.2844 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03940(14) 0.04215(13) 0.02828(12) 0.00161(9) -0.01214(9) -0.00383(9) P1 0.0181(3) 0.0259(4) 0.0201(3) 0.0009(3) 0.0003(3) 0.0019(3) F1 0.0396(10) 0.0493(11) 0.0275(10) 0.0112(8) -0.0001(8) -0.0085(8) F2 0.0319(9) 0.0461(10) 0.0392(10) 0.0026(8) -0.0044(8) -0.0151(8) O1 0.0186(9) 0.0356(11) 0.0307(11) 0.0019(8) -0.0027(8) 0.0051(8) C1 0.0250(15) 0.0303(15) 0.0227(14) -0.0030(11) -0.0058(11) 0.0033(11) C2 0.0284(16) 0.0320(15) 0.0217(14) 0.0037(11) 0.0028(12) 0.0003(12) C3 0.0223(15) 0.0293(15) 0.0300(16) -0.0006(12) -0.0023(12) -0.0044(12) C4 0.0271(15) 0.0313(15) 0.0250(14) 0.0017(12) 0.0018(12) -0.0013(12) C5 0.0244(14) 0.0208(13) 0.0229(14) -0.0011(10) 0.0030(11) -0.0018(11) C6 0.0246(14) 0.0354(16) 0.0254(15) -0.0031(12) 0.0008(12) 0.0047(12) C7 0.0285(16) 0.0396(17) 0.0313(16) 0.0004(13) -0.0067(13) 0.0004(13) C8 0.0453(19) 0.0331(16) 0.0202(14) -0.0029(12) -0.0005(13) -0.0067(14) C9 0.0416(18) 0.0321(16) 0.0279(16) -0.0063(12) 0.0117(14) 0.0032(14) C10 0.0255(14) 0.0325(16) 0.0299(16) 0.0018(12) 0.0056(12) 0.0032(12) C11 0.0228(14) 0.0275(14) 0.0169(13) -0.0025(11) -0.0024(11) 0.0006(11) C12 0.0254(15) 0.0328(15) 0.0247(15) -0.0005(12) 0.0008(12) -0.0035(12) C13 0.0335(17) 0.0322(16) 0.0328(16) 0.0016(13) -0.0055(13) -0.0074(13) C14 0.0401(18) 0.0289(15) 0.0296(16) -0.0041(12) -0.0075(14) 0.0021(13) C15 0.0301(16) 0.0349(16) 0.0322(17) -0.0065(13) 0.0004(13) 0.0102(13) C16 0.0252(15) 0.0352(16) 0.0271(15) -0.0012(12) 0.0019(12) 0.0000(12) _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 I1 C1 2.079(3) . ? P1 O1 1.4869(19) . ? P1 C4 1.786(3) . ? P1 C11 1.805(3) . ? P1 C5 1.807(3) . ? F1 C2 1.343(3) . ? F2 C3 1.347(3) . ? C1 C3 1.378(4) . ? C1 C2 1.382(4) . ? C2 C3 1.380(4) 5_676 ? C3 C2 1.380(4) 5_676 ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C10 1.381(4) . ? C5 C6 1.400(4) . ? C6 C7 1.386(4) . ? C6 H6 0.9500 . ? C7 C8 1.380(4) . ? C7 H7 0.9500 . ? C8 C9 1.379(4) . ? C8 H8 0.9500 . ? C9 C10 1.389(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.395(4) . ? C11 C16 1.395(4) . ? C12 C13 1.381(4) . ? C12 H12 0.9500 . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C15 C16 1.388(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C4 114.66(12) . . ? O1 P1 C11 112.07(12) . . ? C4 P1 C11 106.91(13) . . ? O1 P1 C5 111.01(12) . . ? C4 P1 C5 106.19(13) . . ? C11 P1 C5 105.39(12) . . ? C3 C1 C2 117.6(2) . . ? C3 C1 I1 121.3(2) . . ? C2 C1 I1 121.0(2) . . ? F1 C2 C3 118.8(2) . 5_676 ? F1 C2 C1 120.3(2) . . ? C3 C2 C1 120.9(3) 5_676 . ? F2 C3 C1 120.3(2) . . ? F2 C3 C2 118.2(2) . 5_676 ? C1 C3 C2 121.4(2) . 5_676 ? P1 C4 H4A 109.5 . . ? P1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? P1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C10 C5 C6 119.1(3) . . ? C10 C5 P1 119.2(2) . . ? C6 C5 P1 121.7(2) . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 120.5(3) . . ? C5 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C16 118.7(3) . . ? C12 C11 P1 117.1(2) . . ? C16 C11 P1 124.2(2) . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.9(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.347 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.080 data_(mdppo)(tfib) _database_code_depnum_ccdc_archive 'CCDC 819335' #TrackingRef '- deposit_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; methyldiphenylphosphine oxide: 1,4-diiodotetrafluorobenzene 1/1 ; _chemical_name_common 'methyldiphenylphosphine oxide' _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 O P, C6 F4 I2' _chemical_formula_sum 'C19 H13 F4 I2 O P' _chemical_formula_weight 618.06 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4440(3) _cell_length_b 10.8391(4) _cell_length_c 11.7728(4) _cell_angle_alpha 111.084(2) _cell_angle_beta 110.207(2) _cell_angle_gamma 97.956(2) _cell_volume 1006.63(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 51240 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.545 _exptl_absorpt_correction_T_max 0.694 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 16805 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 32.07 _reflns_number_total 6858 _reflns_number_gt 5659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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. All non-hydrogen atoms have been refined anisotropically and hydrogen atoms have been placed in positions calculated on the basis of the hybridisation state of the belonging carbon atom. ; _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^)+(0.0372P)^2^+1.2686P] 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 6858 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.52285(2) 0.872893(19) 0.771846(18) 0.03045(6) Uani 1 1 d . . . I2 I 1.16604(2) 1.24407(2) 1.40314(2) 0.03693(6) Uani 1 1 d . . . P1 P 0.20093(9) 0.72523(8) 0.41748(7) 0.02859(14) Uani 1 1 d . . . O1 O 0.2405(3) 0.7139(3) 0.5468(2) 0.0400(5) Uani 1 1 d . . . F1 F 0.8400(2) 1.1253(2) 0.88223(19) 0.0404(4) Uani 1 1 d . . . F2 F 1.0845(2) 1.2657(2) 1.1230(2) 0.0406(4) Uani 1 1 d . . . F3 F 0.8658(2) 0.9848(2) 1.2852(2) 0.0457(5) Uani 1 1 d . . . F4 F 0.6242(3) 0.8436(2) 1.0447(2) 0.0471(5) Uani 1 1 d . . . C1 C 0.1730(4) 0.8883(3) 0.4271(4) 0.0400(7) Uani 1 1 d . . . H1A H 0.0905 0.9048 0.4581 0.060 Uiso 1 1 calc R . . H1B H 0.1410 0.8865 0.3379 0.060 Uiso 1 1 calc R . . H1C H 0.2723 0.9626 0.4906 0.060 Uiso 1 1 calc R . . C2 C 0.3509(3) 0.6990(3) 0.3566(3) 0.0290(5) Uani 1 1 d . . . C3 C 0.4250(4) 0.7933(3) 0.3242(3) 0.0323(6) Uani 1 1 d . . . H3 H 0.3977 0.8766 0.3347 0.039 Uiso 1 1 calc R . . C4 C 0.5382(4) 0.7664(3) 0.2766(3) 0.0373(6) Uani 1 1 d . . . H4 H 0.5877 0.8310 0.2544 0.045 Uiso 1 1 calc R . . C5 C 0.5789(4) 0.6461(4) 0.2615(4) 0.0418(7) Uani 1 1 d . . . H5 H 0.6566 0.6280 0.2291 0.050 Uiso 1 1 calc R . . C6 C 0.5067(4) 0.5514(4) 0.2934(4) 0.0467(8) Uani 1 1 d . . . H6 H 0.5348 0.4684 0.2827 0.056 Uiso 1 1 calc R . . C7 C 0.3928(4) 0.5778(3) 0.3413(4) 0.0383(6) Uani 1 1 d . . . H7 H 0.3437 0.5129 0.3635 0.046 Uiso 1 1 calc R . . C8 C 0.0203(3) 0.5954(3) 0.2851(3) 0.0274(5) Uani 1 1 d . . . C9 C -0.0415(4) 0.5871(3) 0.1555(3) 0.0351(6) Uani 1 1 d . . . H9 H 0.0124 0.6512 0.1353 0.042 Uiso 1 1 calc R . . C10 C -0.1817(4) 0.4854(4) 0.0558(3) 0.0433(7) Uani 1 1 d . . . H10 H -0.2247 0.4809 -0.0319 0.052 Uiso 1 1 calc R . . C11 C -0.2582(4) 0.3908(4) 0.0854(4) 0.0435(7) Uani 1 1 d . . . H11 H -0.3531 0.3206 0.0171 0.052 Uiso 1 1 calc R . . C12 C -0.1974(4) 0.3977(3) 0.2139(4) 0.0386(7) Uani 1 1 d . . . H12 H -0.2507 0.3329 0.2337 0.046 Uiso 1 1 calc R . . C13 C -0.0582(3) 0.5000(3) 0.3130(3) 0.0308(5) Uani 1 1 d . . . H13 H -0.0162 0.5048 0.4009 0.037 Uiso 1 1 calc R . . C14 C 0.7226(3) 0.9810(3) 0.9561(3) 0.0287(5) Uani 1 1 d . . . C15 C 0.8442(4) 1.0891(3) 0.9813(3) 0.0295(5) Uani 1 1 d . . . C16 C 0.9710(3) 1.1621(3) 1.1057(3) 0.0296(5) Uani 1 1 d . . . C17 C 0.9824(3) 1.1311(3) 1.2124(3) 0.0301(5) Uani 1 1 d . . . C18 C 0.8628(4) 1.0223(3) 1.1878(3) 0.0327(6) Uani 1 1 d . . . C19 C 0.7364(4) 0.9484(3) 1.0624(3) 0.0325(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03035(10) 0.03156(9) 0.02668(9) 0.01293(7) 0.01031(7) 0.00588(7) I2 0.03021(10) 0.03832(11) 0.03212(10) 0.01263(8) 0.00601(8) 0.00816(8) P1 0.0266(3) 0.0311(3) 0.0226(3) 0.0111(3) 0.0071(3) 0.0036(3) O1 0.0345(11) 0.0497(13) 0.0241(10) 0.0156(10) 0.0048(9) 0.0009(10) F1 0.0454(11) 0.0416(10) 0.0339(9) 0.0222(8) 0.0145(8) 0.0027(8) F2 0.0357(10) 0.0370(9) 0.0414(10) 0.0180(8) 0.0124(8) -0.0027(8) F3 0.0425(11) 0.0578(12) 0.0329(10) 0.0280(10) 0.0088(8) 0.0009(9) F4 0.0417(11) 0.0511(11) 0.0393(11) 0.0246(10) 0.0109(9) -0.0086(9) C1 0.0433(17) 0.0326(14) 0.0388(16) 0.0107(13) 0.0174(14) 0.0097(13) C2 0.0249(12) 0.0296(12) 0.0256(12) 0.0111(10) 0.0065(10) 0.0024(10) C3 0.0317(14) 0.0316(13) 0.0303(13) 0.0158(11) 0.0091(11) 0.0047(11) C4 0.0328(15) 0.0421(16) 0.0323(15) 0.0179(13) 0.0101(12) 0.0032(12) C5 0.0341(16) 0.0487(18) 0.0370(16) 0.0125(15) 0.0164(14) 0.0110(14) C6 0.0399(18) 0.0389(17) 0.061(2) 0.0228(17) 0.0191(17) 0.0132(14) C7 0.0346(15) 0.0303(14) 0.0481(18) 0.0187(14) 0.0151(14) 0.0065(12) C8 0.0248(12) 0.0306(12) 0.0247(12) 0.0120(10) 0.0095(10) 0.0054(10) C9 0.0299(14) 0.0427(16) 0.0272(13) 0.0169(12) 0.0080(11) 0.0015(12) C10 0.0328(15) 0.057(2) 0.0224(13) 0.0112(14) 0.0025(11) 0.0037(14) C11 0.0293(15) 0.0407(17) 0.0447(18) 0.0078(15) 0.0119(14) 0.0051(13) C12 0.0313(14) 0.0316(14) 0.0523(19) 0.0160(14) 0.0215(14) 0.0050(11) C13 0.0311(13) 0.0312(13) 0.0312(13) 0.0149(11) 0.0137(11) 0.0084(11) C14 0.0296(13) 0.0296(12) 0.0234(12) 0.0103(10) 0.0096(10) 0.0074(10) C15 0.0316(13) 0.0301(12) 0.0296(13) 0.0149(11) 0.0144(11) 0.0088(11) C16 0.0285(13) 0.0273(12) 0.0322(13) 0.0128(11) 0.0134(11) 0.0058(10) C17 0.0261(13) 0.0337(14) 0.0283(13) 0.0133(11) 0.0093(11) 0.0098(11) C18 0.0320(14) 0.0390(15) 0.0310(14) 0.0192(12) 0.0138(11) 0.0101(12) C19 0.0309(13) 0.0325(13) 0.0359(15) 0.0172(12) 0.0156(12) 0.0049(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C14 2.091(3) . ? I2 C17 2.072(3) . ? P1 O1 1.493(2) . ? P1 C1 1.792(3) . ? P1 C8 1.800(3) . ? P1 C2 1.807(3) . ? F1 C15 1.348(3) . ? F2 C16 1.343(3) . ? F3 C18 1.341(3) . ? F4 C19 1.341(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C7 1.393(4) . ? C2 C3 1.395(4) . ? C3 C4 1.387(4) . ? C3 H3 0.9500 . ? C4 C5 1.379(5) . ? C4 H4 0.9500 . ? C5 C6 1.386(5) . ? C5 H5 0.9500 . ? C6 C7 1.394(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.387(4) . ? C8 C9 1.396(4) . ? C9 C10 1.392(4) . ? C9 H9 0.9500 . ? C10 C11 1.385(5) . ? C10 H10 0.9500 . ? C11 C12 1.390(5) . ? C11 H11 0.9500 . ? C12 C13 1.388(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.386(4) . ? C14 C19 1.388(4) . ? C15 C16 1.378(4) . ? C16 C17 1.385(4) . ? C17 C18 1.383(4) . ? C18 C19 1.383(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 113.80(16) . . ? O1 P1 C8 111.68(13) . . ? C1 P1 C8 105.75(15) . . ? O1 P1 C2 112.13(14) . . ? C1 P1 C2 107.36(15) . . ? C8 P1 C2 105.57(13) . . ? P1 C1 H1A 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? P1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 119.1(3) . . ? C7 C2 P1 117.6(2) . . ? C3 C2 P1 123.3(2) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 120.1(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C2 C7 C6 120.1(3) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C13 C8 C9 119.4(3) . . ? C13 C8 P1 118.7(2) . . ? C9 C8 P1 121.9(2) . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.6(3) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.7(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 119.5(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C8 C13 C12 120.7(3) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C19 116.5(3) . . ? C15 C14 I1 123.4(2) . . ? C19 C14 I1 120.0(2) . . ? F1 C15 C16 118.2(2) . . ? F1 C15 C14 119.8(3) . . ? C16 C15 C14 121.9(3) . . ? F2 C16 C15 118.8(2) . . ? F2 C16 C17 119.9(3) . . ? C15 C16 C17 121.3(3) . . ? C18 C17 C16 117.2(3) . . ? C18 C17 I2 120.4(2) . . ? C16 C17 I2 122.5(2) . . ? F3 C18 C17 120.9(3) . . ? F3 C18 C19 117.7(3) . . ? C17 C18 C19 121.4(3) . . ? F4 C19 C18 118.6(3) . . ? F4 C19 C14 119.7(3) . . ? C18 C19 C14 121.7(3) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 32.07 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.262 _refine_diff_density_min -1.311 _refine_diff_density_rms 0.125 data_(mdppo)2(tfbb) _database_code_depnum_ccdc_archive 'CCDC 819336' #TrackingRef '- deposit_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; methyldiphenylphosphine oxide: 1,4-dibromotetrafluorobenzene 2/1 ; _chemical_name_common 'methyldiphenylphosphine oxide' _chemical_melting_point ? _chemical_formula_moiety '2(C13 H13 O P), C6 Br2 F4' _chemical_formula_sum 'C32 H26 Br2 F4 O2 P2' _chemical_formula_weight 740.29 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 5.7074(1) _cell_length_b 16.4007(2) _cell_length_c 31.8690(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2983.11(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 18999 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 2.880 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.758 _exptl_absorpt_correction_T_max 0.922 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14509 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3381 _reflns_number_gt 2875 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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. All non-hydrogen atoms have been refined anisotropically and hydrogen atoms have been placed in positions calculated on the basis of the hybridisation state of the belonging carbon atom. ; _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^)+(0.0258P)^2^+2.3191P] 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 3381 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.20323(5) 0.979620(17) 0.412756(8) 0.04509(10) Uani 1 1 d . . . P1 P -0.16858(8) 1.21211(3) 0.321785(15) 0.02168(12) Uani 1 1 d . . . O1 O -0.4222(2) 1.22799(9) 0.31448(4) 0.0288(3) Uani 1 1 d . . . F1 F 0.1009(2) 0.91044(9) 0.49985(4) 0.0440(3) Uani 1 1 d . . . F2 F 0.3482(3) 0.92398(9) 0.57046(4) 0.0454(4) Uani 1 1 d . . . C1 C 0.3719(4) 0.99202(13) 0.46279(7) 0.0306(5) Uani 1 1 d . . . C2 C 0.2982(4) 0.95494(14) 0.49935(7) 0.0307(5) Uani 1 1 d . . . C3 C 0.4244(4) 0.96229(13) 0.53591(7) 0.0315(5) Uani 1 1 d . . . C4 C 0.0256(4) 1.26896(13) 0.28867(6) 0.0274(4) Uani 1 1 d . . . H4A H 0.0097 1.2500 0.2596 0.041 Uiso 1 1 calc R . . H4B H 0.1875 1.2609 0.2981 0.041 Uiso 1 1 calc R . . H4C H -0.0141 1.3270 0.2902 0.041 Uiso 1 1 calc R . . C5 C -0.0948(3) 1.10581(13) 0.31549(6) 0.0242(4) Uani 1 1 d . . . C6 C -0.2528(4) 1.04910(14) 0.33188(7) 0.0294(4) Uani 1 1 d . . . H6 H -0.3934 1.0673 0.3448 0.035 Uiso 1 1 calc R . . C7 C -0.2054(4) 0.96657(14) 0.32939(8) 0.0362(5) Uani 1 1 d . . . H7 H -0.3122 0.9284 0.3411 0.043 Uiso 1 1 calc R . . C8 C -0.0040(4) 0.93929(14) 0.31004(7) 0.0375(5) Uani 1 1 d . . . H8 H 0.0268 0.8825 0.3082 0.045 Uiso 1 1 calc R . . C9 C 0.1532(4) 0.99484(15) 0.29332(8) 0.0375(5) Uani 1 1 d . . . H9 H 0.2912 0.9760 0.2797 0.045 Uiso 1 1 calc R . . C10 C 0.1100(4) 1.07770(14) 0.29635(7) 0.0316(5) Uani 1 1 d . . . H10 H 0.2200 1.1156 0.2854 0.038 Uiso 1 1 calc R . . C11 C -0.0870(3) 1.23705(12) 0.37508(6) 0.0236(4) Uani 1 1 d . . . C12 C 0.1273(4) 1.21206(14) 0.39211(7) 0.0309(5) Uani 1 1 d . . . H12 H 0.2363 1.1829 0.3753 0.037 Uiso 1 1 calc R . . C13 C 0.1801(4) 1.23014(15) 0.43371(7) 0.0353(5) Uani 1 1 d . . . H13 H 0.3242 1.2123 0.4455 0.042 Uiso 1 1 calc R . . C14 C 0.0241(4) 1.27374(13) 0.45786(7) 0.0344(5) Uani 1 1 d . . . H14 H 0.0607 1.2857 0.4863 0.041 Uiso 1 1 calc R . . C15 C -0.1849(4) 1.30018(15) 0.44098(7) 0.0357(5) Uani 1 1 d . . . H15 H -0.2904 1.3312 0.4576 0.043 Uiso 1 1 calc R . . C16 C -0.2415(4) 1.28157(13) 0.39975(7) 0.0296(5) Uani 1 1 d . . . H16 H -0.3865 1.2994 0.3883 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.04736(16) 0.05361(18) 0.03429(14) -0.00092(11) -0.01563(11) -0.00276(12) P1 0.0174(2) 0.0271(3) 0.0206(2) 0.00051(19) -0.00010(18) 0.00137(19) O1 0.0188(7) 0.0381(9) 0.0297(7) 0.0009(6) -0.0024(6) 0.0031(6) F1 0.0324(7) 0.0520(9) 0.0477(8) 0.0005(7) -0.0027(6) -0.0143(6) F2 0.0478(9) 0.0566(9) 0.0318(7) 0.0097(6) 0.0034(6) -0.0086(7) C1 0.0294(11) 0.0335(12) 0.0289(10) -0.0034(9) -0.0066(9) 0.0029(9) C2 0.0242(10) 0.0318(11) 0.0360(11) -0.0014(9) -0.0004(9) -0.0024(9) C3 0.0321(11) 0.0334(12) 0.0289(10) 0.0030(9) 0.0030(9) 0.0001(9) C4 0.0262(10) 0.0310(11) 0.0249(10) 0.0024(8) 0.0024(8) -0.0002(8) C5 0.0224(9) 0.0302(11) 0.0200(9) -0.0018(8) -0.0036(7) 0.0006(8) C6 0.0270(10) 0.0332(11) 0.0281(10) -0.0002(9) 0.0006(8) -0.0016(9) C7 0.0410(13) 0.0316(12) 0.0360(12) 0.0012(9) -0.0034(10) -0.0063(10) C8 0.0424(13) 0.0295(12) 0.0405(13) -0.0046(10) -0.0094(10) 0.0036(10) C9 0.0320(12) 0.0392(13) 0.0412(13) -0.0082(10) 0.0006(10) 0.0087(10) C10 0.0249(10) 0.0356(12) 0.0344(11) -0.0017(9) 0.0026(9) 0.0005(9) C11 0.0227(9) 0.0277(10) 0.0204(9) 0.0006(8) 0.0020(8) -0.0006(8) C12 0.0253(10) 0.0414(13) 0.0261(10) -0.0044(9) 0.0004(8) 0.0043(9) C13 0.0295(11) 0.0479(14) 0.0285(11) -0.0010(10) -0.0064(9) -0.0006(10) C14 0.0455(13) 0.0365(13) 0.0212(10) -0.0039(9) 0.0006(9) -0.0094(10) C15 0.0414(13) 0.0351(13) 0.0305(11) -0.0063(9) 0.0089(10) 0.0025(10) C16 0.0277(10) 0.0313(12) 0.0299(10) 0.0005(9) 0.0038(9) 0.0044(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.874(2) . ? P1 O1 1.4891(15) . ? P1 C4 1.792(2) . ? P1 C5 1.805(2) . ? P1 C11 1.808(2) . ? F1 C2 1.342(2) . ? F2 C3 1.340(2) . ? C1 C2 1.380(3) . ? C1 C3 1.384(3) 5_676 ? C2 C3 1.375(3) . ? C3 C1 1.384(3) 5_676 ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.397(3) . ? C5 C10 1.397(3) . ? C6 C7 1.383(3) . ? C6 H6 0.9500 . ? C7 C8 1.379(3) . ? C7 H7 0.9500 . ? C8 C9 1.385(4) . ? C8 H8 0.9500 . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.389(3) . ? C11 C12 1.400(3) . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 C14 1.377(3) . ? C13 H13 0.9500 . ? C14 C15 1.378(3) . ? C14 H14 0.9500 . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C4 114.72(9) . . ? O1 P1 C5 112.22(9) . . ? C4 P1 C5 107.04(10) . . ? O1 P1 C11 110.96(9) . . ? C4 P1 C11 106.04(10) . . ? C5 P1 C11 105.24(9) . . ? C2 C1 C3 118.0(2) . 5_676 ? C2 C1 Br1 120.95(17) . . ? C3 C1 Br1 121.06(17) 5_676 . ? F1 C2 C3 118.5(2) . . ? F1 C2 C1 120.3(2) . . ? C3 C2 C1 121.2(2) . . ? F2 C3 C2 119.0(2) . . ? F2 C3 C1 120.1(2) . 5_676 ? C2 C3 C1 120.9(2) . 5_676 ? P1 C4 H4A 109.5 . . ? P1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? P1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 118.9(2) . . ? C6 C5 P1 116.83(16) . . ? C10 C5 P1 124.23(16) . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.9(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C5 120.2(2) . . ? C9 C10 H10 119.9 . . ? C5 C10 H10 119.9 . . ? C16 C11 C12 119.28(19) . . ? C16 C11 P1 119.17(16) . . ? C12 C11 P1 121.54(15) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.3(2) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.3(2) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.299 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.058 data_tfib _database_code_depnum_ccdc_archive 'CCDC 819337' #TrackingRef '- deposit_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-diiodotetrafluorobenzene ; _chemical_name_common 1,4-diiodotetrafluorobenzene _chemical_melting_point ? _chemical_formula_moiety 'C6 F4 I2' _chemical_formula_sum 'C6 F4 I2' _chemical_formula_weight 401.86 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.2187(3) _cell_length_b 11.6168(7) _cell_length_c 5.7876(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.61(3) _cell_angle_gamma 90.00 _cell_volume 417.28(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12663 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 7.542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.642 _exptl_absorpt_correction_T_max 0.922 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4851 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1212 _reflns_number_gt 1037 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0447P)^2^+0.5446P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens . _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1212 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.77869(4) 0.36607(2) 0.07136(4) 0.03307(13) Uani 1 1 d . . . F3 F 0.1230(4) 0.4072(2) 0.6249(4) 0.0342(5) Uani 1 1 d . . . F2 F 0.3367(4) 0.3054(2) 0.2966(5) 0.0364(6) Uani 1 1 d . . . C2 C 0.4211(6) 0.4011(4) 0.3970(7) 0.0281(7) Uani 1 1 d . . . C3 C 0.3094(6) 0.4542(4) 0.5649(6) 0.0266(7) Uani 1 1 d . . . C1 C 0.6128(6) 0.4452(3) 0.3287(6) 0.0263(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03294(18) 0.0368(2) 0.03028(18) -0.00145(9) 0.00853(12) 0.00216(10) F3 0.0258(11) 0.0351(13) 0.0425(13) 0.0000(11) 0.0094(10) -0.0033(10) F2 0.0326(13) 0.0334(14) 0.0432(13) -0.0092(10) 0.0030(10) -0.0048(10) C2 0.0257(18) 0.0267(18) 0.0314(19) 0.0001(15) -0.0016(14) 0.0001(15) C3 0.0206(16) 0.030(2) 0.0295(18) 0.0048(14) 0.0015(13) -0.0037(14) C1 0.0249(17) 0.0265(18) 0.0278(17) 0.0013(14) 0.0046(13) 0.0042(14) _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 I1 C1 2.079(4) . ? F3 C3 1.346(4) . ? F2 C2 1.345(5) . ? C2 C3 1.375(6) . ? C2 C1 1.379(5) . ? C3 C1 1.393(6) 3_666 ? C1 C3 1.393(6) 3_666 ? 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 F2 C2 C3 118.4(4) . . ? F2 C2 C1 120.3(4) . . ? C3 C2 C1 121.3(4) . . ? F3 C3 C2 118.8(4) . . ? F3 C3 C1 120.4(3) . 3_666 ? C2 C3 C1 120.8(4) . 3_666 ? C2 C1 C3 117.9(4) . 3_666 ? C2 C1 I1 121.2(3) . . ? C3 C1 I1 120.9(3) 3_666 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.016 _refine_diff_density_min -1.595 _refine_diff_density_rms 0.191 data_(mdppo)2(ofib) _database_code_depnum_ccdc_archive 'CCDC 878592' #TrackingRef '- deposit_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (mdppo)2(ofib) _chemical_melting_point ? _chemical_formula_moiety '2(C13 H13 O P), C4 F8 I2' _chemical_formula_sum 'C30 H26 F8 I2 O2 P2' _chemical_formula_weight 886.25 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.5465(2) _cell_length_b 5.8340(1) _cell_length_c 24.7421(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.269(1) _cell_angle_gamma 90.00 _cell_volume 1666.28(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13065 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 2.055 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.722 _exptl_absorpt_correction_T_max 0.834 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 16708 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 32.02 _reflns_number_total 5692 _reflns_number_gt 3342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0102P)^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 5692 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0474 _refine_ls_wR_factor_gt 0.0463 _refine_ls_goodness_of_fit_ref 0.849 _refine_ls_restrained_S_all 0.849 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.802683(12) 0.30639(2) 0.113180(5) 0.03585(5) Uani 1 1 d . . . F1 F 0.89696(11) 0.11762(16) 0.01614(4) 0.0428(3) Uani 1 1 d . . . F2 F 1.03276(10) 0.20290(17) 0.07470(5) 0.0460(3) Uani 1 1 d . . . F3 F 0.85212(10) 0.56838(18) -0.00090(4) 0.0435(3) Uani 1 1 d . . . F4 F 0.98551(11) 0.66205(15) 0.05898(4) 0.0431(3) Uani 1 1 d . . . C14 C 0.93176(18) 0.2778(3) 0.05270(8) 0.0336(5) Uani 1 1 d . . . C15 C 0.95452(16) 0.5035(3) 0.02208(7) 0.0293(4) Uani 1 1 d . . . P1 P 0.92899(4) 0.56057(7) 0.304787(18) 0.02642(11) Uani 1 1 d . . . O1 O 0.87688(11) 0.79343(17) 0.31210(5) 0.0307(3) Uani 1 1 d . . . C1 C 0.82462(17) 0.3436(2) 0.28782(7) 0.0322(5) Uani 1 1 d . . . H1A H 0.7835 0.3856 0.2542 0.048 Uiso 1 1 calc R . . H1B H 0.7691 0.3297 0.3170 0.048 Uiso 1 1 calc R . . H1C H 0.8642 0.1967 0.2830 0.048 Uiso 1 1 calc R . . C2 C 1.00585(16) 0.4641(3) 0.36510(7) 0.0289(4) Uani 1 1 d . . . C3 C 0.9867(2) 0.2534(3) 0.38902(8) 0.0432(6) Uani 1 1 d . . . H3 H 0.9340 0.1475 0.3727 0.052 Uiso 1 1 calc R . . C4 C 1.0446(2) 0.1977(3) 0.43681(9) 0.0540(7) Uani 1 1 d . . . H4 H 1.0308 0.0534 0.4532 0.065 Uiso 1 1 calc R . . C5 C 1.1209(2) 0.3453(4) 0.46068(8) 0.0542(7) Uani 1 1 d . . . H5 H 1.1588 0.3054 0.4938 0.065 Uiso 1 1 calc R . . C6 C 1.1429(2) 0.5514(4) 0.43678(9) 0.0595(7) Uani 1 1 d . . . H6 H 1.1983 0.6527 0.4527 0.071 Uiso 1 1 calc R . . C7 C 1.0849(2) 0.6133(3) 0.38932(8) 0.0459(6) Uani 1 1 d . . . H7 H 1.0993 0.7583 0.3734 0.055 Uiso 1 1 calc R . . C8 C 1.03164(16) 0.5624(3) 0.25131(7) 0.0281(4) Uani 1 1 d . . . C9 C 1.03432(18) 0.7497(3) 0.21564(8) 0.0354(5) Uani 1 1 d . . . H9 H 0.9836 0.8758 0.2205 0.042 Uiso 1 1 calc R . . C10 C 1.1107(2) 0.7501(3) 0.17351(8) 0.0421(5) Uani 1 1 d . . . H10 H 1.1122 0.8771 0.1495 0.051 Uiso 1 1 calc R . . C11 C 1.18465(19) 0.5688(4) 0.16593(8) 0.0449(5) Uani 1 1 d . . . H11 H 1.2367 0.5701 0.1367 0.054 Uiso 1 1 calc R . . C12 C 1.1829(2) 0.3846(3) 0.20112(9) 0.0455(6) Uani 1 1 d . . . H12 H 1.2343 0.2597 0.1961 0.055 Uiso 1 1 calc R . . C13 C 1.10723(19) 0.3808(3) 0.24327(8) 0.0371(5) Uani 1 1 d . . . H13 H 1.1066 0.2531 0.2671 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.04247(9) 0.03281(7) 0.03262(7) 0.00130(6) 0.00912(5) 0.00064(7) F1 0.0534(8) 0.0309(6) 0.0448(7) -0.0073(5) 0.0161(6) -0.0042(5) F2 0.0398(8) 0.0475(7) 0.0507(7) 0.0223(6) 0.0014(6) 0.0111(6) F3 0.0331(7) 0.0503(7) 0.0472(7) 0.0166(6) 0.0029(5) 0.0118(6) F4 0.0649(9) 0.0322(6) 0.0328(6) -0.0077(5) 0.0113(6) -0.0082(6) C14 0.0342(12) 0.0311(10) 0.0354(11) 0.0020(8) 0.0001(9) 0.0061(9) C15 0.0321(12) 0.0270(9) 0.0287(10) 0.0001(7) -0.0020(8) 0.0037(8) P1 0.0281(3) 0.0224(2) 0.0286(3) -0.00027(19) -0.0014(2) -0.0003(2) O1 0.0371(8) 0.0218(6) 0.0333(7) -0.0009(5) 0.0019(6) 0.0055(6) C1 0.0336(12) 0.0254(9) 0.0373(11) -0.0007(8) -0.0062(9) -0.0010(8) C2 0.0297(11) 0.0283(9) 0.0287(10) -0.0028(7) 0.0003(8) 0.0012(8) C3 0.0574(16) 0.0350(11) 0.0369(12) 0.0059(8) -0.0079(11) -0.0071(10) C4 0.0731(19) 0.0478(13) 0.0408(13) 0.0161(11) -0.0096(12) 0.0018(13) C5 0.0597(17) 0.0706(16) 0.0318(12) 0.0054(11) -0.0138(12) 0.0046(13) C6 0.0543(17) 0.0698(16) 0.0533(15) -0.0038(13) -0.0242(13) -0.0171(13) C7 0.0489(15) 0.0462(12) 0.0423(13) 0.0052(10) -0.0089(11) -0.0153(11) C8 0.0315(12) 0.0272(9) 0.0254(10) -0.0009(8) -0.0022(8) 0.0006(9) C9 0.0395(13) 0.0322(10) 0.0343(11) 0.0028(7) -0.0012(10) 0.0025(9) C10 0.0492(15) 0.0440(12) 0.0332(12) 0.0067(8) 0.0035(11) -0.0068(10) C11 0.0382(14) 0.0619(14) 0.0349(12) -0.0041(11) 0.0074(10) -0.0013(12) C12 0.0419(15) 0.0471(12) 0.0478(14) -0.0034(10) 0.0068(11) 0.0140(11) C13 0.0401(14) 0.0342(10) 0.0373(12) 0.0029(8) 0.0037(10) 0.0063(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C14 2.142(2) . ? F1 C14 1.355(2) . ? F2 C14 1.349(2) . ? F3 C15 1.355(2) . ? F4 C15 1.3427(18) . ? C14 C15 1.545(2) . ? C15 C15 1.533(4) 3_765 ? P1 O1 1.4983(11) . ? P1 C1 1.7914(16) . ? P1 C8 1.7958(19) . ? P1 C2 1.8089(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.385(2) . ? C2 C7 1.387(2) . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.357(3) . ? C4 H4 0.9500 . ? C5 C6 1.366(3) . ? C5 H5 0.9500 . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.390(2) . ? C8 C9 1.405(2) . ? C9 C10 1.380(3) . ? C9 H9 0.9500 . ? C10 C11 1.375(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 C13 1.375(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 F2 C14 F1 106.68(14) . . ? F2 C14 C15 108.61(16) . . ? F1 C14 C15 108.16(14) . . ? F2 C14 I1 110.61(12) . . ? F1 C14 I1 108.63(13) . . ? C15 C14 I1 113.88(12) . . ? F4 C15 F3 108.05(13) . . ? F4 C15 C15 109.06(19) . 3_765 ? F3 C15 C15 108.28(17) . 3_765 ? F4 C15 C14 107.43(14) . . ? F3 C15 C14 106.72(15) . . ? C15 C15 C14 116.98(18) 3_765 . ? O1 P1 C1 113.53(8) . . ? O1 P1 C8 110.91(8) . . ? C1 P1 C8 106.44(8) . . ? O1 P1 C2 111.92(7) . . ? C1 P1 C2 106.79(8) . . ? C8 P1 C2 106.85(8) . . ? P1 C1 H1A 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? P1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 118.83(16) . . ? C3 C2 P1 123.27(13) . . ? C7 C2 P1 117.86(13) . . ? C4 C3 C2 119.63(18) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 121.31(19) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.67(19) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 120.3(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 120.23(19) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C13 C8 C9 118.70(19) . . ? C13 C8 P1 121.86(14) . . ? C9 C8 P1 119.43(14) . . ? C10 C9 C8 119.95(19) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 120.71(19) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 120.51(19) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.489 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.076