# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_2007src1393 #TrackingRef 'web_deposit_cif_file_0_MuhammadSohail_1362321010.Muhammad Sohail (6-9).cif' # It was not possible to determine the absolute # configuration of the crystal structure from the # diffraction data. _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dr P. G. Taylor ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 F N O2 Si' _chemical_formula_weight 203.29 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 0.0000 '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' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 2(1) 2(1) 2(1)' 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' _cell_length_a 8.6460(2) _cell_length_b 8.9974(3) _cell_length_c 12.8915(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1002.85(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9296 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6325 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9929 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1344 _reflns_number_gt 1173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON/PLUTON (Spek, A. L., 1998)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0135P)^2^+0.9275P] 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_abs_structure_Flack ? _chemical_absolute_configuration unk _refine_ls_number_reflns 1344 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.000 _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 C1 C 0.1874(3) 0.2335(4) 0.3039(2) 0.0234(6) Uani 1 1 d . . . C2 C 0.2711(4) 0.1982(4) 0.4019(3) 0.0284(7) Uani 1 1 d . . . H2A H 0.3411 0.1128 0.3897 0.034 Uiso 1 1 calc R . . H2B H 0.1951 0.1684 0.4555 0.034 Uiso 1 1 calc R . . C3 C 0.3645(4) 0.3282(4) 0.4416(3) 0.0327(8) Uani 1 1 d . . . H3A H 0.4261 0.2976 0.5028 0.039 Uiso 1 1 calc R . . H3B H 0.2947 0.4099 0.4628 0.039 Uiso 1 1 calc R . . C4 C 0.4716(4) 0.3806(4) 0.3552(3) 0.0330(8) Uani 1 1 d . . . H4A H 0.5277 0.4704 0.3787 0.040 Uiso 1 1 calc R . . H4B H 0.5492 0.3022 0.3410 0.040 Uiso 1 1 calc R . . C5 C 0.3870(4) 0.4157(4) 0.2571(3) 0.0268(7) Uani 1 1 d . . . C6 C 0.1609(4) 0.3707(4) 0.1423(2) 0.0231(7) Uani 1 1 d . . . H6A H 0.2339 0.3648 0.0833 0.028 Uiso 1 1 calc R . . H6B H 0.1229 0.4743 0.1458 0.028 Uiso 1 1 calc R . . C7 C 0.0389(4) 0.0514(4) 0.0771(3) 0.0305(8) Uani 1 1 d . . . H7A H -0.0139 0.0254 0.0124 0.046 Uiso 1 1 calc R . . H7B H 0.0047 -0.0156 0.1325 0.046 Uiso 1 1 calc R . . H7C H 0.1509 0.0416 0.0677 0.046 Uiso 1 1 calc R . . C8 C -0.1970(4) 0.2797(4) 0.1780(3) 0.0307(8) Uani 1 1 d . . . H8A H -0.1976 0.3793 0.2086 0.046 Uiso 1 1 calc R . . H8B H -0.2123 0.2054 0.2326 0.046 Uiso 1 1 calc R . . H8C H -0.2808 0.2718 0.1270 0.046 Uiso 1 1 calc R . . N1 N 0.2477(3) 0.3395(3) 0.2382(2) 0.0227(6) Uani 1 1 d . . . O1 O 0.0674(2) 0.1700(2) 0.27854(18) 0.0260(5) Uani 1 1 d . . . O2 O 0.4314(3) 0.5056(3) 0.1933(2) 0.0347(6) Uani 1 1 d . . . F1 F -0.0430(2) 0.3208(2) -0.00151(16) 0.0363(5) Uani 1 1 d . . . Si1 Si -0.00857(9) 0.24654(10) 0.11283(6) 0.0233(2) 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 C1 0.0209(13) 0.0227(15) 0.0265(14) -0.0016(14) 0.0037(12) 0.0043(13) C2 0.0227(14) 0.0366(18) 0.0259(16) 0.0034(15) 0.0020(14) 0.0059(14) C3 0.0264(16) 0.042(2) 0.0296(17) -0.0085(17) -0.0031(15) 0.0053(16) C4 0.0214(16) 0.0339(18) 0.044(2) -0.0117(16) -0.0025(15) -0.0011(14) C5 0.0242(15) 0.0207(16) 0.0356(19) -0.0095(15) 0.0067(14) -0.0001(13) C6 0.0242(15) 0.0224(15) 0.0227(15) 0.0016(13) 0.0034(13) -0.0018(13) C7 0.0309(17) 0.0307(17) 0.0299(17) -0.0074(15) 0.0016(14) -0.0014(15) C8 0.0236(15) 0.0292(19) 0.0394(19) 0.0016(16) -0.0001(14) 0.0000(13) N1 0.0205(12) 0.0217(13) 0.0259(14) -0.0010(12) 0.0019(11) -0.0022(10) O1 0.0215(10) 0.0260(12) 0.0305(12) 0.0047(10) 0.0002(10) -0.0044(10) O2 0.0309(12) 0.0277(13) 0.0456(15) -0.0029(12) 0.0094(12) -0.0089(11) F1 0.0393(11) 0.0409(11) 0.0289(10) 0.0095(9) -0.0058(9) -0.0012(10) Si1 0.0233(4) 0.0233(4) 0.0234(4) 0.0016(4) 0.0006(3) -0.0004(4) _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 C1 O1 1.229(4) . ? C1 N1 1.377(4) . ? C1 C2 1.491(4) . ? C2 C3 1.511(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.494(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O2 1.216(4) . ? C5 N1 1.407(4) . ? C6 N1 1.474(4) . ? C6 Si1 1.881(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 Si1 1.861(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 Si1 1.857(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? F1 Si1 1.645(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 118.6(3) . . ? O1 C1 C2 122.4(3) . . ? N1 C1 C2 119.0(3) . . ? C1 C2 C3 112.4(3) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 108.4(3) . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C5 C4 C3 112.8(3) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? O2 C5 N1 118.5(3) . . ? O2 C5 C4 124.0(3) . . ? N1 C5 C4 117.5(3) . . ? N1 C6 Si1 117.0(2) . . ? N1 C6 H6A 108.1 . . ? Si1 C6 H6A 108.1 . . ? N1 C6 H6B 108.1 . . ? Si1 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 N1 C5 123.7(3) . . ? C1 N1 C6 117.0(3) . . ? C5 N1 C6 119.2(3) . . ? F1 Si1 C8 100.44(14) . . ? F1 Si1 C7 101.60(14) . . ? C8 Si1 C7 117.17(15) . . ? F1 Si1 C6 94.63(13) . . ? C8 Si1 C6 119.79(15) . . ? C7 Si1 C6 116.00(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.325 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 927438' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_2008src0138 #TrackingRef 'web_deposit_cif_file_0_MuhammadSohail_1362321010.Muhammad Sohail (6-9).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Professor Peter Taylor ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 F3 N O5 S Si' _chemical_formula_weight 333.36 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3636(2) _cell_length_b 8.8564(4) _cell_length_c 18.6451(8) _cell_angle_alpha 91.671(2) _cell_angle_beta 94.616(3) _cell_angle_gamma 93.374(3) _cell_volume 1373.40(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 21313 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9388 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission from SADABS: 0.5598 and 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19824 _diffrn_reflns_av_R_equivalents 0.0946 _diffrn_reflns_av_sigmaI/netI 0.0924 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5555 _reflns_number_gt 3821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON/PLUTON (Spek, A. L., 1998)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0000P)^2^+9.8846P] 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 5555 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.1868 _refine_ls_wR_factor_gt 0.1601 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.000 _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 C1 C 0.7326(7) 1.1971(7) -0.1503(3) 0.0235(13) Uani 1 1 d . . . C2 C 0.7543(7) 1.3374(7) -0.1931(3) 0.0265(13) Uani 1 1 d . . . H2A H 0.6843 1.3252 -0.2386 0.032 Uiso 1 1 calc R . . H2B H 0.8671 1.3481 -0.2058 0.032 Uiso 1 1 calc R . . C3 C 0.7151(8) 1.4812(7) -0.1531(3) 0.0268(14) Uani 1 1 d . . . H3A H 0.5984 1.4793 -0.1473 0.032 Uiso 1 1 calc R . . H3B H 0.7442 1.5706 -0.1811 0.032 Uiso 1 1 calc R . . C4 C 0.8087(8) 1.4923(7) -0.0794(3) 0.0270(14) Uani 1 1 d . . . H4A H 0.9246 1.5107 -0.0855 0.032 Uiso 1 1 calc R . . H4B H 0.7736 1.5791 -0.0513 0.032 Uiso 1 1 calc R . . C5 C 0.7831(6) 1.3513(6) -0.0395(3) 0.0201(12) Uani 1 1 d . . . C6 C 0.7266(7) 1.0874(6) -0.0280(3) 0.0221(12) Uani 1 1 d . . . H6A H 0.8091 1.0146 -0.0364 0.027 Uiso 1 1 calc R . . H6B H 0.6191 1.0350 -0.0387 0.027 Uiso 1 1 calc R . . C7 C 0.5761(7) 1.2317(7) 0.1111(3) 0.0267(14) Uani 1 1 d . . . H7A H 0.5302 1.1522 0.1402 0.040 Uiso 1 1 calc R . . H7B H 0.4948 1.2590 0.0737 0.040 Uiso 1 1 calc R . . H7C H 0.6107 1.3209 0.1420 0.040 Uiso 1 1 calc R . . C8 C 0.9492(7) 1.1653(7) 0.1211(3) 0.0283(14) Uani 1 1 d . . . H8A H 0.9614 1.2542 0.1541 0.042 Uiso 1 1 calc R . . H8B H 1.0349 1.1703 0.0882 0.042 Uiso 1 1 calc R . . H8C H 0.9562 1.0732 0.1489 0.042 Uiso 1 1 calc R . . C9 C 0.7689(7) 0.7401(7) 0.1802(3) 0.0287(14) Uani 1 1 d . . . N1 N 0.7454(5) 1.2183(5) -0.0747(3) 0.0197(10) Uani 1 1 d . . . O1 O 0.7073(5) 1.0706(5) -0.1762(2) 0.0322(10) Uani 1 1 d . . . O2 O 0.7992(5) 1.3526(4) 0.0283(2) 0.0234(9) Uani 1 1 d . . . O3 O 0.6830(5) 0.9486(4) 0.0960(2) 0.0239(9) Uani 1 1 d . . . O4 O 0.6118(5) 0.6890(5) 0.0565(2) 0.0311(10) Uani 1 1 d . . . O5 O 0.8914(5) 0.7883(5) 0.0594(2) 0.0303(10) Uani 1 1 d . . . F1 F 0.8809(4) 0.8306(4) 0.2162(2) 0.0352(9) Uani 1 1 d . . . F2 F 0.8159(5) 0.5980(4) 0.1833(2) 0.0397(10) Uani 1 1 d . . . F3 F 0.6347(5) 0.7473(5) 0.2134(2) 0.0424(10) Uani 1 1 d . . . Si1 Si 0.75085(19) 1.16167(19) 0.06848(9) 0.0213(4) Uani 1 1 d . . . S1 S 0.73643(17) 0.79370(16) 0.08698(8) 0.0216(3) Uani 1 1 d . . . C101 C 0.7920(7) 0.7175(7) 0.6491(3) 0.0213(12) Uani 1 1 d . . . C102 C 0.8343(7) 0.8636(7) 0.6911(3) 0.0268(14) Uani 1 1 d . . . H10A H 0.9522 0.8743 0.7025 0.032 Uiso 1 1 calc R . . H10B H 0.7834 0.8598 0.7372 0.032 Uiso 1 1 calc R . . C103 C 0.7813(7) 1.0018(7) 0.6513(3) 0.0272(14) Uani 1 1 d . . . H10C H 0.8245 1.0948 0.6787 0.033 Uiso 1 1 calc R . . H10D H 0.6625 1.0016 0.6473 0.033 Uiso 1 1 calc R . . C104 C 0.8418(7) 1.0013(7) 0.5760(3) 0.0255(13) Uani 1 1 d . . . H10E H 0.7939 1.0833 0.5482 0.031 Uiso 1 1 calc R . . H10F H 0.9600 1.0205 0.5800 0.031 Uiso 1 1 calc R . . C105 C 0.7983(6) 0.8543(6) 0.5379(3) 0.0204(12) Uani 1 1 d . . . C106 C 0.7324(7) 0.5903(6) 0.5271(3) 0.0204(12) Uani 1 1 d . . . H10G H 0.6273 0.5423 0.5377 0.025 Uiso 1 1 calc R . . H10H H 0.8154 0.5163 0.5360 0.025 Uiso 1 1 calc R . . C107 C 0.9045(7) 0.6424(7) 0.3796(3) 0.0281(14) Uani 1 1 d . . . H10I H 0.8964 0.5512 0.3482 0.042 Uiso 1 1 calc R . . H10J H 1.0003 0.6410 0.4135 0.042 Uiso 1 1 calc R . . H10K H 0.9127 0.7322 0.3503 0.042 Uiso 1 1 calc R . . C108 C 0.5367(7) 0.7115(7) 0.3845(3) 0.0239(13) Uani 1 1 d . . . H10L H 0.5620 0.7997 0.3560 0.036 Uiso 1 1 calc R . . H10M H 0.4635 0.7389 0.4205 0.036 Uiso 1 1 calc R . . H10N H 0.4854 0.6295 0.3526 0.036 Uiso 1 1 calc R . . C109 C 0.6868(7) 0.2081(7) 0.3193(4) 0.0288(14) Uani 1 1 d . . . N101 N 0.7714(5) 0.7262(5) 0.5735(3) 0.0197(10) Uani 1 1 d . . . O101 O 0.7769(5) 0.5950(5) 0.6751(2) 0.0302(10) Uani 1 1 d . . . O102 O 0.7867(5) 0.8452(4) 0.4698(2) 0.0236(9) Uani 1 1 d . . . O103 O 0.6453(5) 0.4313(4) 0.4040(2) 0.0239(9) Uani 1 1 d . . . O104 O 0.8698(5) 0.2761(5) 0.4359(2) 0.0297(10) Uani 1 1 d . . . O105 O 0.5915(5) 0.1809(5) 0.4469(2) 0.0294(10) Uani 1 1 d . . . F101 F 0.5363(4) 0.2110(5) 0.2903(2) 0.0441(11) Uani 1 1 d . . . F102 F 0.7315(5) 0.0676(4) 0.3148(2) 0.0483(11) Uani 1 1 d . . . F103 F 0.7808(4) 0.2942(4) 0.2799(2) 0.0369(9) Uani 1 1 d . . . Si11 Si 0.72414(19) 0.64775(18) 0.43021(9) 0.0208(4) Uani 1 1 d . . . S101 S 0.70249(17) 0.27825(16) 0.41251(8) 0.0220(3) 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 C1 0.021(3) 0.030(3) 0.021(3) 0.002(3) 0.008(2) 0.005(2) C2 0.029(3) 0.025(3) 0.026(3) 0.004(3) 0.004(3) 0.001(2) C3 0.033(3) 0.021(3) 0.027(3) 0.007(3) 0.003(3) -0.001(2) C4 0.034(3) 0.024(3) 0.023(3) 0.001(3) 0.003(3) 0.002(3) C5 0.017(3) 0.021(3) 0.022(3) -0.001(2) 0.000(2) 0.001(2) C6 0.025(3) 0.019(3) 0.022(3) 0.002(2) 0.003(2) 0.000(2) C7 0.025(3) 0.027(3) 0.028(4) 0.001(3) 0.006(3) 0.005(2) C8 0.028(3) 0.030(3) 0.025(3) 0.001(3) -0.003(3) -0.001(3) C9 0.031(3) 0.029(3) 0.026(4) 0.010(3) -0.001(3) 0.006(3) N1 0.024(2) 0.018(2) 0.017(3) -0.002(2) 0.006(2) 0.0021(19) O1 0.043(3) 0.028(3) 0.025(2) -0.006(2) 0.002(2) 0.004(2) O2 0.032(2) 0.018(2) 0.019(2) 0.0019(17) -0.0010(17) 0.0010(17) O3 0.029(2) 0.019(2) 0.024(2) 0.0066(17) 0.0027(17) 0.0041(17) O4 0.031(2) 0.026(2) 0.034(3) -0.002(2) -0.0049(19) -0.0002(18) O5 0.023(2) 0.033(3) 0.036(3) 0.004(2) 0.0077(19) 0.0040(18) F1 0.039(2) 0.034(2) 0.030(2) 0.0019(17) -0.0103(17) -0.0042(16) F2 0.049(2) 0.027(2) 0.043(2) 0.0144(18) -0.0039(19) 0.0037(17) F3 0.038(2) 0.065(3) 0.027(2) 0.008(2) 0.0136(17) 0.0031(19) Si1 0.0225(8) 0.0228(9) 0.0187(9) -0.0001(7) 0.0007(6) 0.0033(6) S1 0.0219(7) 0.0202(7) 0.0228(8) 0.0031(6) 0.0013(6) 0.0024(5) C101 0.019(3) 0.024(3) 0.022(3) 0.002(2) 0.004(2) 0.005(2) C102 0.027(3) 0.035(4) 0.019(3) 0.006(3) -0.002(2) 0.004(3) C103 0.027(3) 0.026(3) 0.028(4) -0.002(3) -0.003(3) 0.003(2) C104 0.030(3) 0.020(3) 0.027(3) 0.003(3) 0.007(3) 0.002(2) C105 0.018(3) 0.022(3) 0.022(3) 0.008(2) 0.000(2) 0.002(2) C106 0.027(3) 0.016(3) 0.018(3) 0.000(2) 0.002(2) 0.003(2) C107 0.029(3) 0.025(3) 0.030(4) 0.000(3) 0.005(3) 0.001(2) C108 0.027(3) 0.024(3) 0.021(3) 0.004(2) 0.000(2) 0.005(2) C109 0.022(3) 0.033(4) 0.031(4) -0.010(3) 0.006(3) -0.002(3) N101 0.018(2) 0.020(2) 0.021(3) 0.003(2) 0.0026(19) 0.0014(18) O101 0.039(3) 0.026(2) 0.026(2) 0.0053(19) 0.0042(19) 0.0020(19) O102 0.028(2) 0.022(2) 0.021(2) 0.0030(17) 0.0015(17) 0.0027(17) O103 0.025(2) 0.020(2) 0.026(2) -0.0008(17) 0.0006(17) 0.0034(16) O104 0.020(2) 0.032(2) 0.037(3) 0.004(2) -0.0002(19) 0.0062(18) O105 0.028(2) 0.029(2) 0.033(3) 0.007(2) 0.0061(19) 0.0022(18) F101 0.030(2) 0.071(3) 0.028(2) -0.012(2) 0.0002(17) -0.0075(19) F102 0.059(3) 0.031(2) 0.056(3) -0.014(2) 0.019(2) -0.0010(19) F103 0.036(2) 0.047(2) 0.029(2) -0.0020(18) 0.0138(17) -0.0030(17) Si11 0.0221(8) 0.0210(8) 0.0196(9) 0.0024(7) 0.0013(6) 0.0030(6) S101 0.0214(7) 0.0207(7) 0.0242(8) 0.0003(6) 0.0018(6) 0.0030(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.206(7) . ? C1 N1 1.412(7) . ? C1 C2 1.506(8) . ? C2 C3 1.523(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.523(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.486(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O2 1.260(7) . ? C5 N1 1.340(7) . ? C6 N1 1.478(7) . ? C6 Si1 1.889(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 Si1 1.848(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 Si1 1.857(6) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 F1 1.324(7) . ? C9 F3 1.329(7) . ? C9 F2 1.342(7) . ? C9 S1 1.818(6) . ? O2 Si1 1.904(4) . ? O3 S1 1.477(4) . ? O3 Si1 2.030(4) . ? O4 S1 1.424(4) . ? O5 S1 1.436(4) . ? C101 O101 1.206(7) . ? C101 N101 1.412(7) . ? C101 C102 1.501(9) . ? C102 C103 1.519(8) . ? C102 H10A 0.9900 . ? C102 H10B 0.9900 . ? C103 C104 1.529(8) . ? C103 H10C 0.9900 . ? C103 H10D 0.9900 . ? C104 C105 1.477(8) . ? C104 H10E 0.9900 . ? C104 H10F 0.9900 . ? C105 O102 1.267(7) . ? C105 N101 1.347(7) . ? C106 N101 1.466(7) . ? C106 Si11 1.889(6) . ? C106 H10G 0.9900 . ? C106 H10H 0.9900 . ? C107 Si11 1.844(6) . ? C107 H10I 0.9800 . ? C107 H10J 0.9800 . ? C107 H10K 0.9800 . ? C108 Si11 1.849(6) . ? C108 H10L 0.9800 . ? C108 H10M 0.9800 . ? C108 H10N 0.9800 . ? C109 F102 1.322(7) . ? C109 F101 1.331(7) . ? C109 F103 1.340(7) . ? C109 S101 1.820(7) . ? O102 Si11 1.905(4) . ? O103 S101 1.473(4) . ? O103 Si11 2.023(4) . ? O104 S101 1.433(4) . ? O105 S101 1.431(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 C1 N1 119.0(5) . . ? O1 C1 C2 124.7(6) . . ? N1 C1 C2 116.3(5) . . ? C1 C2 C3 113.3(5) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 109.5(5) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 111.2(5) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? O2 C5 N1 118.1(5) . . ? O2 C5 C4 121.1(5) . . ? N1 C5 C4 120.8(5) . . ? N1 C6 Si1 107.6(4) . . ? N1 C6 H6A 110.2 . . ? Si1 C6 H6A 110.2 . . ? N1 C6 H6B 110.2 . . ? Si1 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F1 C9 F3 107.7(5) . . ? F1 C9 F2 108.1(5) . . ? F3 C9 F2 108.4(5) . . ? F1 C9 S1 111.4(4) . . ? F3 C9 S1 110.8(4) . . ? F2 C9 S1 110.3(4) . . ? C5 N1 C1 124.7(5) . . ? C5 N1 C6 114.8(5) . . ? C1 N1 C6 120.4(5) . . ? C5 O2 Si1 114.1(4) . . ? S1 O3 Si1 138.3(3) . . ? C7 Si1 C8 119.6(3) . . ? C7 Si1 C6 119.9(3) . . ? C8 Si1 C6 120.5(3) . . ? C7 Si1 O2 92.4(2) . . ? C8 Si1 O2 92.5(2) . . ? C6 Si1 O2 85.1(2) . . ? C7 Si1 O3 89.1(2) . . ? C8 Si1 O3 94.3(2) . . ? C6 Si1 O3 86.6(2) . . ? O2 Si1 O3 171.16(19) . . ? O4 S1 O5 117.5(3) . . ? O4 S1 O3 113.0(3) . . ? O5 S1 O3 113.7(3) . . ? O4 S1 C9 104.4(3) . . ? O5 S1 C9 104.6(3) . . ? O3 S1 C9 101.2(3) . . ? O101 C101 N101 118.4(5) . . ? O101 C101 C102 125.0(5) . . ? N101 C101 C102 116.7(5) . . ? C101 C102 C103 113.4(5) . . ? C101 C102 H10A 108.9 . . ? C103 C102 H10A 108.9 . . ? C101 C102 H10B 108.9 . . ? C103 C102 H10B 108.9 . . ? H10A C102 H10B 107.7 . . ? C102 C103 C104 110.3(5) . . ? C102 C103 H10C 109.6 . . ? C104 C103 H10C 109.6 . . ? C102 C103 H10D 109.6 . . ? C104 C103 H10D 109.6 . . ? H10C C103 H10D 108.1 . . ? C105 C104 C103 110.5(5) . . ? C105 C104 H10E 109.5 . . ? C103 C104 H10E 109.5 . . ? C105 C104 H10F 109.5 . . ? C103 C104 H10F 109.5 . . ? H10E C104 H10F 108.1 . . ? O102 C105 N101 117.8(5) . . ? O102 C105 C104 120.2(5) . . ? N101 C105 C104 122.0(5) . . ? N101 C106 Si11 108.4(4) . . ? N101 C106 H10G 110.0 . . ? Si11 C106 H10G 110.0 . . ? N101 C106 H10H 110.0 . . ? Si11 C106 H10H 110.0 . . ? H10G C106 H10H 108.4 . . ? Si11 C107 H10I 109.5 . . ? Si11 C107 H10J 109.5 . . ? H10I C107 H10J 109.5 . . ? Si11 C107 H10K 109.5 . . ? H10I C107 H10K 109.5 . . ? H10J C107 H10K 109.5 . . ? Si11 C108 H10L 109.5 . . ? Si11 C108 H10M 109.5 . . ? H10L C108 H10M 109.5 . . ? Si11 C108 H10N 109.5 . . ? H10L C108 H10N 109.5 . . ? H10M C108 H10N 109.5 . . ? F102 C109 F101 108.6(5) . . ? F102 C109 F103 108.1(5) . . ? F101 C109 F103 107.8(5) . . ? F102 C109 S101 110.9(5) . . ? F101 C109 S101 110.6(4) . . ? F103 C109 S101 110.7(4) . . ? C105 N101 C101 123.8(5) . . ? C105 N101 C106 114.7(5) . . ? C101 N101 C106 121.3(5) . . ? C105 O102 Si11 114.2(4) . . ? S101 O103 Si11 138.3(3) . . ? C107 Si11 C108 118.8(3) . . ? C107 Si11 C106 120.3(3) . . ? C108 Si11 C106 120.9(3) . . ? C107 Si11 O102 92.3(2) . . ? C108 Si11 O102 92.6(2) . . ? C106 Si11 O102 84.8(2) . . ? C107 Si11 O103 94.9(2) . . ? C108 Si11 O103 89.0(2) . . ? C106 Si11 O103 86.6(2) . . ? O102 Si11 O103 170.76(19) . . ? O105 S101 O104 118.0(3) . . ? O105 S101 O103 112.1(2) . . ? O104 S101 O103 114.0(3) . . ? O105 S101 C109 104.5(3) . . ? O104 S101 C109 104.9(3) . . ? O103 S101 C109 101.0(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.472 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 927439' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_2009src0169 #TrackingRef 'web_deposit_cif_file_0_MuhammadSohail_1362321010.Muhammad Sohail (6-9).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 I N O2 Si' _chemical_formula_weight 311.19 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' N N 0.0061 0.0033 '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' Si Si 0.0817 0.0704 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4342(3) _cell_length_b 7.2543(2) _cell_length_c 9.6610(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.079(2) _cell_angle_gamma 90.00 _cell_volume 575.73(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8450 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 2.857 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6273 _exptl_absorpt_correction_T_max 0.8943 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6956 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2582 _reflns_number_gt 2426 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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. ADDSYM suggest space group P21/m, resulting in a glide plane along the plane of the molecule. However, as C4 is out of the plane of the rest of the moelcule, this would mean that this atom appears as disordered. Therefore it was deemed more correct to keep the structure in P21. Instead the Flack parameter suggested a 'racemic twin', suggesting that whether C4 is above or below the plane of the ring is dependent upon its neighbours within a layer and therefore each layer can take a different conformation. The 'racemic twin' refined with a batch scale factor of 0.48158. ; _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^)+(0.0000P)^2^+0.7104P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(4) _refine_ls_number_reflns 2582 _refine_ls_number_parameters 121 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0495 _refine_ls_wR_factor_gt 0.0481 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.002 _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 C2 C 1.0658(4) 0.2828(14) 0.3683(3) 0.0157(13) Uani 1 1 d . . . C3 C 1.1481(5) 0.2637(6) 0.5196(4) 0.0224(13) Uani 1 1 d . . . H3A H 1.1565 0.1315 0.5458 0.027 Uiso 1 1 calc R . . H3B H 1.0831 0.3261 0.5791 0.027 Uiso 1 1 calc R . . C4 C 1.3174(4) 0.3480(5) 0.5476(4) 0.0224(11) Uani 1 1 d . . . H4A H 1.3088 0.4836 0.5372 0.027 Uiso 1 1 calc R . . H4B H 1.3767 0.3197 0.6459 0.027 Uiso 1 1 calc R . . C5 C 1.4095(4) 0.2709(9) 0.4436(4) 0.0216(15) Uani 1 1 d . . . H5A H 1.5162 0.3338 0.4578 0.026 Uiso 1 1 calc R . . H5B H 1.4305 0.1382 0.4638 0.026 Uiso 1 1 calc R . . C6 C 1.3205(4) 0.2929(18) 0.2912(3) 0.0163(9) Uani 1 1 d . . . C7 C 1.0460(3) 0.3053(19) 0.1184(3) 0.0151(6) Uani 1 1 d . . . H7A H 1.0686 0.2002 0.0603 0.018 Uiso 1 1 calc R . . H7B H 1.0668 0.4220 0.0723 0.018 Uiso 1 1 calc R . . C8 C 0.7130(13) 0.0831(11) 0.1018(10) 0.0172(16) Uani 1 1 d . . . H8A H 0.7839 -0.0234 0.1323 0.026 Uiso 1 1 calc R . . H8B H 0.6679 0.0759 -0.0009 0.026 Uiso 1 1 calc R . . H8C H 0.6239 0.0827 0.1517 0.026 Uiso 1 1 calc R . . C9 C 0.7221(13) 0.5153(11) 0.1195(11) 0.023(2) Uani 1 1 d . . . H9A H 0.6308 0.5098 0.1666 0.035 Uiso 1 1 calc R . . H9B H 0.6806 0.5387 0.0178 0.035 Uiso 1 1 calc R . . H9C H 0.7961 0.6149 0.1612 0.035 Uiso 1 1 calc R . . N1 N 1.1457(3) 0.2937(14) 0.2658(2) 0.0139(7) Uani 1 1 d . . . O2 O 0.9084(3) 0.2834(12) 0.3305(2) 0.0214(11) Uani 1 1 d . . . O6 O 1.3820(2) 0.3013(11) 0.1909(2) 0.0211(5) Uani 1 1 d . . . Si1 Si 0.83140(10) 0.2964(5) 0.14348(8) 0.0152(2) Uani 1 1 d . . . I1 I 1.18985(2) -0.19733(3) 0.248333(18) 0.01931(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 C2 0.0154(14) 0.015(4) 0.0169(14) -0.002(2) 0.0038(11) -0.003(2) C3 0.0243(19) 0.028(4) 0.0129(15) 0.0029(15) 0.0010(13) -0.0001(16) C4 0.0176(18) 0.028(3) 0.0175(17) -0.0053(14) -0.0045(14) -0.0010(14) C5 0.0132(16) 0.028(5) 0.0194(15) -0.0016(17) -0.0048(12) 0.0030(16) C6 0.0120(14) 0.013(3) 0.0241(14) 0.000(4) 0.0038(11) -0.006(3) C7 0.0170(14) 0.0162(14) 0.0109(12) 0.000(5) 0.0006(10) -0.005(5) C8 0.013(3) 0.021(3) 0.019(3) -0.002(2) 0.007(2) -0.004(3) C9 0.021(4) 0.020(3) 0.025(4) 0.002(3) -0.001(3) -0.002(3) N1 0.0123(11) 0.0138(18) 0.0148(11) -0.004(3) 0.0013(9) 0.002(3) O2 0.0121(10) 0.036(3) 0.0161(10) 0.0050(19) 0.0039(8) 0.0007(19) O6 0.0142(10) 0.0247(12) 0.0253(11) -0.002(4) 0.0062(9) 0.006(4) Si1 0.0119(4) 0.0170(5) 0.0162(4) 0.0032(11) 0.0020(3) 0.0024(11) I1 0.02050(11) 0.01563(10) 0.02004(10) -0.0010(2) 0.00093(7) -0.0005(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 O2 1.295(4) . ? C2 N1 1.320(4) . ? C2 C3 1.476(4) . ? C3 C4 1.520(5) . ? C4 C5 1.510(5) . ? C5 C6 1.502(5) . ? C6 O6 1.200(4) . ? C6 N1 1.438(4) . ? C7 N1 1.484(3) . ? C7 Si1 1.881(3) . ? C8 Si1 1.837(9) . ? C9 Si1 1.824(9) . ? O2 Si1 1.779(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C2 N1 117.0(3) . . ? O2 C2 C3 120.1(3) . . ? N1 C2 C3 122.9(3) . . ? C2 C3 C4 110.5(4) . . ? C5 C4 C3 109.7(3) . . ? C6 C5 C4 113.2(4) . . ? O6 C6 N1 118.4(3) . . ? O6 C6 C5 125.8(3) . . ? N1 C6 C5 115.7(3) . . ? N1 C7 Si1 103.13(18) . . ? C2 N1 C6 123.3(3) . . ? C2 N1 C7 116.7(2) . . ? C6 N1 C7 120.0(2) . . ? C2 O2 Si1 113.7(2) . . ? O2 Si1 C9 103.5(4) . . ? O2 Si1 C8 103.5(4) . . ? C9 Si1 C8 118.13(16) . . ? O2 Si1 C7 89.55(11) . . ? C9 Si1 C7 115.3(6) . . ? C8 Si1 C7 119.5(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.510 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 927440' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_2007src1682 #TrackingRef 'web_deposit_cif_file_0_MuhammadSohail_1362321010.Muhammad Sohail (6-9).cif' #TrackingRef 'web_deposit_cif_file_0_MuhammadSohail_1362321010.Muhammad Sohail (6-9).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Prof. Peter Taylor ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H11 F2 N O2 Si' _chemical_formula_weight 207.26 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/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 12.7138(4) _cell_length_b 7.4295(3) _cell_length_c 9.7496(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.419(2) _cell_angle_gamma 90.00 _cell_volume 920.10(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5837 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9899 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 8251 reflections reduced R(int) from 0.3941 to 0.0624 Ratio of minimum to maximum apparent transmission: 0.729767 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9042 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2101 _reflns_number_gt 1714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON/PLUTON (Spek, A. L., 1998)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0190P)^2^+1.7725P] 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 2101 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _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 C1 C 0.73552(19) -0.0951(3) 0.9515(3) 0.0195(5) Uani 1 1 d . . . C2 C 0.88705(19) 0.0249(4) 1.0849(3) 0.0207(5) Uani 1 1 d . . . C3 C 0.8925(2) -0.1474(4) 1.1651(3) 0.0251(6) Uani 1 1 d . . . H3A H 0.8497 -0.1347 1.2470 0.030 Uiso 1 1 calc R . . H3B H 0.9663 -0.1686 1.1975 0.030 Uiso 1 1 calc R . . C4 C 0.8537(2) -0.3094(4) 1.0828(3) 0.0244(6) Uani 1 1 d . . . H4A H 0.8533 -0.4172 1.1425 0.029 Uiso 1 1 calc R . . H4B H 0.9013 -0.3331 1.0070 0.029 Uiso 1 1 calc R . . C5 C 0.7424(2) -0.2714(4) 1.0244(3) 0.0241(6) Uani 1 1 d . . . H5A H 0.7209 -0.3687 0.9597 0.029 Uiso 1 1 calc R . . H5B H 0.6929 -0.2714 1.1001 0.029 Uiso 1 1 calc R . . C6 C 0.79278(19) 0.2065(3) 0.9030(3) 0.0200(5) Uani 1 1 d . . . H6A H 0.8517 0.2224 0.8409 0.024 Uiso 1 1 calc R . . H6B H 0.7950 0.3080 0.9689 0.024 Uiso 1 1 calc R . . C7 C 0.5332(2) 0.2320(4) 0.8679(3) 0.0271(6) Uani 1 1 d . . . H7A H 0.5066 0.3550 0.8557 0.041 Uiso 1 1 calc R . . H7B H 0.5371 0.2020 0.9658 0.041 Uiso 1 1 calc R . . H7C H 0.4856 0.1478 0.8190 0.041 Uiso 1 1 calc R . . N1 N 0.80819(15) 0.0373(3) 0.9793(2) 0.0182(4) Uani 1 1 d . . . O1 O 0.66392(14) -0.0619(3) 0.86458(19) 0.0257(4) Uani 1 1 d . . . O2 O 0.94483(15) 0.1526(3) 1.1067(2) 0.0283(5) Uani 1 1 d . . . F1 F 0.66898(13) 0.1244(2) 0.65016(16) 0.0296(4) Uani 1 1 d . . . F2 F 0.68347(12) 0.4231(2) 0.74679(17) 0.0285(4) Uani 1 1 d . . . Si1 Si 0.66499(5) 0.21546(10) 0.79877(7) 0.01969(19) 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 C1 0.0180(11) 0.0229(13) 0.0178(12) -0.0011(10) 0.0021(10) 0.0000(10) C2 0.0165(11) 0.0284(14) 0.0173(12) -0.0034(11) 0.0025(9) 0.0023(10) C3 0.0208(12) 0.0326(15) 0.0217(13) 0.0038(12) -0.0005(10) 0.0058(11) C4 0.0234(13) 0.0220(14) 0.0278(14) 0.0055(11) 0.0019(11) 0.0056(10) C5 0.0241(13) 0.0210(13) 0.0272(14) 0.0061(11) 0.0006(11) 0.0000(11) C6 0.0198(12) 0.0171(12) 0.0230(13) 0.0030(10) 0.0005(10) -0.0007(10) C7 0.0197(12) 0.0317(15) 0.0299(15) 0.0009(12) 0.0001(11) 0.0004(11) N1 0.0150(9) 0.0205(11) 0.0188(10) 0.0001(9) -0.0015(8) -0.0002(8) O1 0.0227(9) 0.0260(10) 0.0276(10) 0.0038(8) -0.0088(8) -0.0039(8) O2 0.0242(9) 0.0318(11) 0.0282(10) -0.0037(9) -0.0054(8) -0.0048(8) F1 0.0344(9) 0.0332(9) 0.0209(8) -0.0010(7) -0.0008(7) 0.0046(7) F2 0.0270(8) 0.0237(8) 0.0346(9) 0.0074(7) 0.0002(7) 0.0009(7) Si1 0.0180(3) 0.0210(4) 0.0200(4) 0.0019(3) -0.0003(3) 0.0010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.242(3) . ? C1 N1 1.368(3) . ? C1 C5 1.491(4) . ? C2 O2 1.214(3) . ? C2 N1 1.409(3) . ? C2 C3 1.500(4) . ? C3 C4 1.518(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.529(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.470(3) . ? C6 Si1 1.881(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 Si1 1.836(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? O1 Si1 2.159(2) . ? F1 Si1 1.6017(17) . ? F2 Si1 1.6437(17) . ? 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 C1 N1 117.5(2) . . ? O1 C1 C5 121.7(2) . . ? N1 C1 C5 120.8(2) . . ? O2 C2 N1 118.9(2) . . ? O2 C2 C3 124.2(2) . . ? N1 C2 C3 116.9(2) . . ? C2 C3 C4 113.2(2) . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.8 . . ? C3 C4 C5 109.0(2) . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C1 C5 C4 112.0(2) . . ? C1 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C1 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N1 C6 Si1 113.42(17) . . ? N1 C6 H6A 108.9 . . ? Si1 C6 H6A 108.9 . . ? N1 C6 H6B 108.9 . . ? Si1 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 N1 C2 123.5(2) . . ? C1 N1 C6 116.1(2) . . ? C2 N1 C6 120.1(2) . . ? C1 O1 Si1 112.23(17) . . ? F1 Si1 F2 96.14(9) . . ? F1 Si1 C7 115.11(11) . . ? F2 Si1 C7 101.24(11) . . ? F1 Si1 C6 114.47(11) . . ? F2 Si1 C6 93.92(10) . . ? C7 Si1 C6 125.80(12) . . ? F1 Si1 O1 82.33(8) . . ? F2 Si1 O1 172.06(8) . . ? C7 Si1 O1 86.41(11) . . ? C6 Si1 O1 79.74(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.466 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 927441' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_ssg1394 #TrackingRef 'web_deposit_cif_file_0_MuhammadSohail_1362321010.Muhammad Sohail (6-9).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H28 N2 O5 Si2' _chemical_formula_sum 'C16 H28 N2 O5 Si2' _chemical_formula_weight 384.58 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' N N 0.0061 0.0033 '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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 12.501(2) _cell_length_b 6.1661(10) _cell_length_c 13.596(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.413(2) _cell_angle_gamma 90.00 _cell_volume 975.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3225 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 29.18 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.001 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6893 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX2 CCD diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 7490 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.51 _reflns_number_total 1977 _reflns_number_gt 1660 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0367P)^2^+0.5211P] 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 1977 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _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 Si Si 0.63445(4) 0.43791(7) 0.53702(3) 0.01874(14) Uani 1 1 d . . . N N 0.63516(11) 0.4992(2) 0.33090(10) 0.0206(3) Uani 1 1 d . . . O1 O 0.76149(10) 0.2233(2) 0.35280(10) 0.0321(3) Uani 1 1 d . . . O2 O 0.52722(11) 0.80607(19) 0.29922(9) 0.0309(3) Uani 1 1 d . . . O3 O 0.5000 0.5000 0.5000 0.0297(4) Uani 1 2 d S . . C1 C 0.67589(14) 0.3167(3) 0.29495(13) 0.0242(4) Uani 1 1 d . . . C2 C 0.61129(15) 0.2443(3) 0.18349(13) 0.0292(4) Uani 1 1 d . . . H2A H 0.6137 0.0840 0.1805 0.035 Uiso 1 1 calc R . . H2B H 0.6502 0.3022 0.1374 0.035 Uiso 1 1 calc R . . C3 C 0.48713(15) 0.3177(3) 0.14128(13) 0.0301(4) Uani 1 1 d . . . H3A H 0.4444 0.2468 0.1811 0.036 Uiso 1 1 calc R . . H3B H 0.4502 0.2776 0.0659 0.036 Uiso 1 1 calc R . . C4 C 0.48506(14) 0.5627(3) 0.15373(12) 0.0273(4) Uani 1 1 d . . . H4A H 0.5200 0.6319 0.1069 0.033 Uiso 1 1 calc R . . H4B H 0.4043 0.6120 0.1310 0.033 Uiso 1 1 calc R . . C5 C 0.54885(14) 0.6355(3) 0.26581(12) 0.0236(3) Uani 1 1 d . . . C6 C 0.69486(13) 0.5656(3) 0.44243(12) 0.0218(3) Uani 1 1 d . . . H6A H 0.6901 0.7253 0.4472 0.026 Uiso 1 1 calc R . . H6B H 0.7771 0.5264 0.4645 0.026 Uiso 1 1 calc R . . C7 C 0.71164(15) 0.5601(3) 0.66822(12) 0.0276(4) Uani 1 1 d . . . H7A H 0.6835 0.4961 0.7202 0.041 Uiso 1 1 calc R . . H7B H 0.6981 0.7170 0.6646 0.041 Uiso 1 1 calc R . . H7C H 0.7942 0.5320 0.6894 0.041 Uiso 1 1 calc R . . C8 C 0.64763(14) 0.1396(3) 0.53679(13) 0.0250(4) Uani 1 1 d . . . H8A H 0.6159 0.0768 0.5865 0.038 Uiso 1 1 calc R . . H8B H 0.7288 0.0996 0.5581 0.038 Uiso 1 1 calc R . . H8C H 0.6052 0.0840 0.4656 0.038 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 Si 0.0195(2) 0.0204(2) 0.0154(2) 0.00074(16) 0.00526(16) 0.00161(17) N 0.0219(7) 0.0229(7) 0.0173(6) -0.0014(5) 0.0076(5) 0.0003(5) O1 0.0289(7) 0.0346(7) 0.0331(6) 0.0004(5) 0.0116(5) 0.0085(5) O2 0.0355(7) 0.0266(6) 0.0286(6) -0.0002(5) 0.0094(5) 0.0065(5) O3 0.0219(8) 0.0383(10) 0.0303(9) 0.0111(7) 0.0111(7) 0.0081(7) C1 0.0265(9) 0.0253(9) 0.0248(8) -0.0021(7) 0.0143(7) -0.0015(7) C2 0.0344(9) 0.0290(9) 0.0275(8) -0.0070(7) 0.0151(7) -0.0024(7) C3 0.0311(9) 0.0361(10) 0.0234(8) -0.0056(7) 0.0102(7) -0.0065(8) C4 0.0258(8) 0.0344(9) 0.0200(8) 0.0004(7) 0.0063(7) -0.0007(7) C5 0.0230(8) 0.0266(8) 0.0227(8) 0.0029(7) 0.0102(6) -0.0011(6) C6 0.0220(8) 0.0245(8) 0.0186(7) -0.0015(6) 0.0069(6) -0.0013(6) C7 0.0365(9) 0.0233(8) 0.0199(8) -0.0004(7) 0.0066(7) -0.0005(7) C8 0.0270(9) 0.0218(8) 0.0249(8) -0.0014(7) 0.0077(7) 0.0002(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si O3 1.6147(5) . ? Si C6 1.8849(16) . ? Si C7 1.8504(16) . ? Si C8 1.8470(17) . ? N C1 1.395(2) . ? N C5 1.398(2) . ? N C6 1.4823(19) . ? O1 C1 1.217(2) . ? O2 C5 1.215(2) . ? O3 Si 1.6147(5) 3_666 ? C1 C2 1.501(2) . ? C2 H2A 0.990 . ? C2 H2B 0.990 . ? C2 C3 1.514(2) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.521(2) . ? C4 H4A 0.990 . ? C4 H4B 0.990 . ? C4 C5 1.507(2) . ? C6 H6A 0.990 . ? C6 H6B 0.990 . ? C7 H7A 0.980 . ? C7 H7B 0.980 . ? C7 H7C 0.980 . ? C8 H8A 0.980 . ? C8 H8B 0.980 . ? C8 H8C 0.980 . ? 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 O3 Si C6 108.60(5) . . ? O3 Si C7 108.73(6) . . ? O3 Si C8 108.60(6) . . ? C6 Si C7 106.85(7) . . ? C6 Si C8 110.89(7) . . ? C7 Si C8 113.06(8) . . ? C1 N C5 123.97(13) . . ? C1 N C6 117.97(13) . . ? C5 N C6 117.75(13) . . ? Si O3 Si 180.0 . 3_666 ? N C1 O1 120.18(15) . . ? N C1 C2 117.56(14) . . ? O1 C1 C2 122.26(15) . . ? C1 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C1 C2 C3 113.14(14) . . ? H2A C2 H2B 107.8 . . ? H2A C2 C3 109.0 . . ? H2B C2 C3 109.0 . . ? C2 C3 H3A 110.1 . . ? C2 C3 H3B 110.1 . . ? C2 C3 C4 108.14(14) . . ? H3A C3 H3B 108.4 . . ? H3A C3 C4 110.1 . . ? H3B C3 C4 110.1 . . ? C3 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C3 C4 C5 112.56(14) . . ? H4A C4 H4B 107.8 . . ? H4A C4 C5 109.1 . . ? H4B C4 C5 109.1 . . ? N C5 O2 120.60(14) . . ? N C5 C4 117.54(14) . . ? O2 C5 C4 121.86(15) . . ? Si C6 N 113.91(10) . . ? Si C6 H6A 108.8 . . ? Si C6 H6B 108.8 . . ? N C6 H6A 108.8 . . ? N C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? Si C7 H7A 109.5 . . ? Si C7 H7B 109.5 . . ? Si C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si C8 H8A 109.5 . . ? Si C8 H8B 109.5 . . ? Si C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N C1 O1 169.82(15) . . . . ? C5 N C1 C2 -9.5(2) . . . . ? C6 N C1 O1 -3.7(2) . . . . ? C6 N C1 C2 177.02(13) . . . . ? N C1 C2 C3 -24.0(2) . . . . ? O1 C1 C2 C3 156.76(16) . . . . ? C1 C2 C3 C4 54.70(19) . . . . ? C2 C3 C4 C5 -54.91(18) . . . . ? C1 N C5 O2 -170.78(15) . . . . ? C1 N C5 C4 8.9(2) . . . . ? C6 N C5 O2 2.8(2) . . . . ? C6 N C5 C4 -177.52(13) . . . . ? C3 C4 C5 N 24.7(2) . . . . ? C3 C4 C5 O2 -155.57(16) . . . . ? C1 N C6 Si -90.02(14) . . . . ? C5 N C6 Si 96.04(14) . . . . ? O3 Si C6 N -57.87(12) . . . . ? C7 Si C6 N -175.00(11) . . . . ? C8 Si C6 N 61.38(13) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.409 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 927442' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_sm18f3 #TrackingRef 'web_deposit_cif_file_0_MuhammadSohail_1362545998.SM18F3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Prof. Peter Taylor' _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 F3 N O2 Si' _chemical_formula_sum 'C6 H8 F3 N O2 Si' _chemical_formula_weight 211.22 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 11.1244(6) _cell_length_b 9.2761(5) _cell_length_c 7.9793(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 823.39(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7374 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 34.44 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9067 _exptl_absorpt_correction_T_max 0.9392 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11659 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 32.00 _reflns_number_total 2860 _reflns_number_gt 2789 _reflns_threshold_expression I>2u(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _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^)+(0.0316P)^2^+0.153P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 2860 _refine_ls_number_parameters 118 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0556 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.990 _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 Si1 Si 0.59159(2) 0.61522(3) 0.80294(4) 0.01670(6) Uani 1 1 d U . . F3 F 0.61042(7) 0.63472(7) 0.60609(8) 0.02518(13) Uani 1 1 d U . . F2 F 0.46757(6) 0.68440(7) 0.86045(9) 0.02541(14) Uani 1 1 d U . . C2 C 0.53234(8) 0.33005(9) 0.80914(13) 0.01629(15) Uani 1 1 d U . . F1 F 0.67399(6) 0.75253(7) 0.85690(10) 0.02869(15) Uani 1 1 d U . . N1 N 0.62842(7) 0.33795(8) 0.91126(10) 0.01488(13) Uani 1 1 d U . . O2 O 0.76337(7) 0.23715(8) 1.08774(10) 0.02417(15) Uani 1 1 d U . . O1 O 0.49604(7) 0.44511(8) 0.74384(9) 0.01942(14) Uani 1 1 d U . . C1 C 0.67984(8) 0.48220(10) 0.92935(13) 0.01613(15) Uani 1 1 d U . . H1A H 0.7645 0.4816 0.8909 0.019 Uiso 1 1 calc R . . H1B H 0.6787 0.5108 1.0489 0.019 Uiso 1 1 calc R . . C6 C 0.68170(9) 0.21806(11) 0.99095(12) 0.01792(16) Uani 1 1 d U . . C3 C 0.47239(9) 0.19008(10) 0.77254(13) 0.02114(18) Uani 1 1 d U . . H3A H 0.5003 0.1541 0.6624 0.025 Uiso 1 1 calc R . . H3B H 0.3845 0.2055 0.7653 0.025 Uiso 1 1 calc R . . C4 C 0.49838(10) 0.07673(11) 0.90604(14) 0.02321(19) Uani 1 1 d U . . H4A H 0.4713 -0.0191 0.8664 0.028 Uiso 1 1 calc R . . H4B H 0.4538 0.1002 1.0099 0.028 Uiso 1 1 calc R . . C5 C 0.63303(10) 0.07291(11) 0.94235(14) 0.02281(19) Uani 1 1 d U . . H5A H 0.6486 0.0037 1.0342 0.027 Uiso 1 1 calc R . . H5B H 0.6760 0.0382 0.8415 0.027 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 Si1 0.01779(10) 0.01254(10) 0.01977(11) 0.00019(9) 0.00216(10) 0.00187(8) F3 0.0310(3) 0.0239(3) 0.0207(3) 0.0065(2) 0.0047(2) 0.0060(2) F2 0.0216(3) 0.0204(3) 0.0342(3) -0.0031(2) 0.0052(3) 0.0058(2) C2 0.0168(3) 0.0153(3) 0.0168(3) -0.0014(3) 0.0001(4) 0.0000(3) F1 0.0289(3) 0.0137(2) 0.0435(4) -0.0008(3) -0.0019(3) -0.0034(2) N1 0.0164(3) 0.0125(3) 0.0158(3) -0.0001(3) -0.0013(3) -0.0005(3) O2 0.0225(3) 0.0263(3) 0.0238(4) 0.0061(3) -0.0045(3) 0.0012(3) O1 0.0211(3) 0.0160(3) 0.0211(3) 0.0003(2) -0.0051(2) 0.0013(2) C1 0.0168(3) 0.0141(3) 0.0176(4) -0.0014(3) -0.0003(3) -0.0021(3) C6 0.0185(4) 0.0174(4) 0.0179(4) 0.0040(3) 0.0028(3) 0.0020(3) C3 0.0221(4) 0.0159(4) 0.0255(5) -0.0026(3) -0.0042(3) -0.0030(3) C4 0.0249(4) 0.0151(4) 0.0297(5) 0.0004(3) 0.0023(4) -0.0034(3) C5 0.0265(5) 0.0141(4) 0.0278(5) 0.0033(3) 0.0011(4) 0.0016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 F2 1.5893(7) . ? Si1 F3 1.5950(7) . ? Si1 F1 1.6273(7) . ? Si1 C1 1.8718(10) . ? Si1 O1 1.9601(8) . ? C2 O1 1.2545(11) . ? C2 N1 1.3461(12) . ? C2 C3 1.4886(12) . ? N1 C6 1.4116(12) . ? N1 C1 1.4624(11) . ? O2 C6 1.2055(13) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C6 C5 1.5021(15) . ? C3 C4 1.5243(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5261(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? 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 Si1 F3 110.65(4) . . ? F2 Si1 F1 95.54(4) . . ? F3 Si1 F1 95.61(4) . . ? F2 Si1 C1 124.46(4) . . ? F3 Si1 C1 122.45(4) . . ? F1 Si1 C1 94.47(4) . . ? F2 Si1 O1 85.63(3) . . ? F3 Si1 O1 85.73(4) . . ? F1 Si1 O1 177.77(4) . . ? C1 Si1 O1 83.31(4) . . ? O1 C2 N1 117.43(8) . . ? O1 C2 C3 121.09(8) . . ? N1 C2 C3 121.47(8) . . ? C2 N1 C6 124.28(8) . . ? C2 N1 C1 114.84(8) . . ? C6 N1 C1 120.82(8) . . ? C2 O1 Si1 114.23(6) . . ? N1 C1 Si1 110.17(6) . . ? N1 C1 H1A 109.6 . . ? Si1 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? Si1 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? O2 C6 N1 119.29(9) . . ? O2 C6 C5 124.66(9) . . ? N1 C6 C5 116.01(8) . . ? C2 C3 C4 112.31(9) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 109.56(9) . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C6 C5 C4 112.46(9) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? 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 O1 C2 N1 C6 -178.45(9) . . . . ? C3 C2 N1 C6 0.58(15) . . . . ? O1 C2 N1 C1 -1.31(13) . . . . ? C3 C2 N1 C1 177.73(8) . . . . ? N1 C2 O1 Si1 1.14(11) . . . . ? C3 C2 O1 Si1 -177.89(7) . . . . ? F2 Si1 O1 C2 -125.99(8) . . . . ? F3 Si1 O1 C2 122.89(7) . . . . ? F1 Si1 O1 C2 -4.3(11) . . . . ? C1 Si1 O1 C2 -0.52(7) . . . . ? C2 N1 C1 Si1 0.81(10) . . . . ? C6 N1 C1 Si1 178.06(7) . . . . ? F2 Si1 C1 N1 79.83(7) . . . . ? F3 Si1 C1 N1 -80.77(7) . . . . ? F1 Si1 C1 N1 179.68(7) . . . . ? O1 Si1 C1 N1 -0.17(6) . . . . ? C2 N1 C6 O2 -175.80(9) . . . . ? C1 N1 C6 O2 7.21(14) . . . . ? C2 N1 C6 C5 6.14(14) . . . . ? C1 N1 C6 C5 -170.84(8) . . . . ? O1 C2 C3 C4 -159.51(10) . . . . ? N1 C2 C3 C4 21.50(13) . . . . ? C2 C3 C4 C5 -47.95(12) . . . . ? O2 C6 C5 C4 147.45(10) . . . . ? N1 C6 C5 C4 -34.62(12) . . . . ? C3 C4 C5 C6 55.17(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 32.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.318 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 927443'