# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_name 'Barnes, Nicholas' _publ_contact_author_email 'nick barnes28@hotmail.com' loop_ _publ_author_name N.Barnes R.Pritchard data_1 _database_code_depnum_ccdc_archive 'CCDC 865498' #TrackingRef '- Compound1.cif' _audit_creation_date 2010-07-06T14:20:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 I4 P1' _chemical_formula_sum 'C21 H21 I4 P' _chemical_formula_weight 811.78 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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 10.5042(3) _cell_length_b 13.5441(5) _cell_length_c 17.1378(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2438.19(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3417 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 2.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_absorpt_correction_T_min 0.4911 _exptl_absorpt_correction_T_max 0.8601 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.265773E-1 _diffrn_orient_matrix_ub_12 -0.14486E-1 _diffrn_orient_matrix_ub_13 -0.548485E-1 _diffrn_orient_matrix_ub_21 -0.389247E-1 _diffrn_orient_matrix_ub_22 0.671891E-1 _diffrn_orient_matrix_ub_23 -0.39977E-2 _diffrn_orient_matrix_ub_31 0.827137E-1 _diffrn_orient_matrix_ub_32 0.269643E-1 _diffrn_orient_matrix_ub_33 -0.19505E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.092 _diffrn_reflns_av_unetI/netI 0.0824 _diffrn_reflns_number 22813 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 4526 _reflns_number_gt 3559 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. TWIN and BASF were used to refine the Flack parameter, which indicates a racemic twin. ; _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^)+(0.0790P)^2^+45.0472P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4526 _refine_ls_number_parameters 239 _refine_ls_number_restraints 156 _refine_ls_R_factor_all 0.1094 _refine_ls_R_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.2026 _refine_ls_wR_factor_gt 0.1784 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.58(10) _refine_diff_density_max 2.277 _refine_diff_density_min -2.674 _refine_diff_density_rms 0.318 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' 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 -0.2185(15) -0.0338(15) 0.7641(11) 0.036(4) Uani 1 1 d U . . C2 C -0.2484(15) -0.0504(13) 0.6853(12) 0.030(4) Uani 1 1 d U . . H2 H -0.2276 -0.0025 0.6468 0.037 Uiso 1 1 calc R . . C3 C -0.3082(18) -0.1370(14) 0.6644(13) 0.038(5) Uani 1 1 d U . . H3 H -0.3238 -0.151 0.6109 0.046 Uiso 1 1 calc R . . C4 C -0.347(2) -0.2050(17) 0.7221(14) 0.049(5) Uani 1 1 d U . . H4 H -0.3918 -0.2628 0.7073 0.059 Uiso 1 1 calc R . . C5 C -0.3203(19) -0.1894(17) 0.7965(14) 0.047(5) Uani 1 1 d U . . H5 H -0.3469 -0.2373 0.8336 0.057 Uiso 1 1 calc R . . C6 C -0.2545(19) -0.1047(16) 0.8238(13) 0.044(5) Uani 1 1 d U . . C7 C -0.2352(18) -0.0929(15) 0.9090(12) 0.041(5) Uani 1 1 d U . . H7A H -0.3169 -0.1008 0.9359 0.061 Uiso 1 1 calc R . . H7B H -0.2009 -0.027 0.9197 0.061 Uiso 1 1 calc R . . H7C H -0.1752 -0.143 0.9276 0.061 Uiso 1 1 calc R . . C8 C -0.2079(19) 0.1592(14) 0.8552(12) 0.036(4) Uani 1 1 d U . . C9 C -0.3261(19) 0.1323(15) 0.8830(12) 0.038(5) Uani 1 1 d U . . H9 H -0.3627 0.0715 0.8668 0.046 Uiso 1 1 calc R . . C10 C -0.393(2) 0.1929(16) 0.9345(13) 0.048(5) Uani 1 1 d U . . H10 H -0.4748 0.1746 0.9526 0.058 Uiso 1 1 calc R . . C11 C -0.336(2) 0.2813(18) 0.9591(14) 0.052(6) Uani 1 1 d U . . H11 H -0.3771 0.3214 0.9971 0.062 Uiso 1 1 calc R . . C12 C -0.222(2) 0.3095(15) 0.9282(13) 0.042(5) Uani 1 1 d U . . H12 H -0.1889 0.3723 0.9425 0.05 Uiso 1 1 calc R . . C13 C -0.151(2) 0.2511(16) 0.8769(13) 0.043(5) Uani 1 1 d U . . C14 C -0.028(2) 0.2907(17) 0.8429(15) 0.052(6) Uani 1 1 d U . . H14A H -0.039 0.303 0.787 0.078 Uiso 1 1 calc R . . H14B H 0.0401 0.2422 0.8507 0.078 Uiso 1 1 calc R . . H14C H -0.0052 0.3526 0.8692 0.078 Uiso 1 1 calc R . . C15 C -0.0820(19) 0.1354(14) 0.6990(11) 0.037(4) Uani 1 1 d U . . C16 C 0.0338(19) 0.1196(15) 0.6638(12) 0.039(5) Uani 1 1 d U . . H16 H 0.0944 0.0796 0.6901 0.046 Uiso 1 1 calc R . . C17 C 0.066(2) 0.1577(14) 0.5942(12) 0.040(4) Uani 1 1 d U . . H17 H 0.1476 0.1461 0.5721 0.048 Uiso 1 1 calc R . . C18 C -0.024(2) 0.2144(15) 0.5558(13) 0.040(5) Uani 1 1 d U . . H18 H -0.003 0.2411 0.5062 0.048 Uiso 1 1 calc R . . C19 C -0.1443(18) 0.2341(14) 0.5868(11) 0.037(4) Uani 1 1 d U . . H19 H -0.2023 0.2749 0.5591 0.044 Uiso 1 1 calc R . . C20 C -0.1792(18) 0.1938(15) 0.6585(12) 0.036(4) Uani 1 1 d U . . C21 C -0.3101(19) 0.2155(16) 0.6903(14) 0.042(5) Uani 1 1 d U . . H21A H -0.3041 0.2667 0.7305 0.063 Uiso 1 1 calc R . . H21B H -0.346 0.1553 0.7132 0.063 Uiso 1 1 calc R . . H21C H -0.3653 0.2385 0.648 0.063 Uiso 1 1 calc R . . P1 P -0.1288(5) 0.0753(4) 0.7894(3) 0.0370(11) Uani 1 1 d U . . I1 I 0.06792(11) 0.02083(11) 0.85021(7) 0.0414(3) Uani 1 1 d U . . I2 I 0.37222(11) -0.02653(10) 0.90736(7) 0.0396(3) Uani 1 1 d U . . I3 I 0.40320(10) 0.00952(10) 0.73665(7) 0.0386(3) Uani 1 1 d U . . I4 I 0.43592(13) 0.05121(10) 0.57465(8) 0.0451(4) Uani 1 1 d U . . 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 0.022(6) 0.050(8) 0.036(7) -0.010(7) -0.008(6) -0.011(6) C2 0.028(7) 0.026(7) 0.038(7) 0.002(6) 0.003(6) -0.007(6) C3 0.034(7) 0.036(8) 0.044(9) -0.007(7) -0.007(7) -0.002(6) C4 0.047(8) 0.049(8) 0.051(9) -0.002(7) -0.006(7) 0.004(7) C5 0.041(8) 0.046(8) 0.056(9) 0.009(7) 0.006(7) -0.001(7) C6 0.039(8) 0.053(9) 0.040(8) -0.003(7) -0.001(7) 0.011(7) C7 0.035(9) 0.046(10) 0.041(10) -0.005(9) -0.014(8) -0.005(8) C8 0.040(8) 0.037(8) 0.031(8) -0.002(7) 0.003(7) -0.003(6) C9 0.043(8) 0.036(8) 0.036(8) 0.009(7) 0.001(7) 0.005(7) C10 0.044(8) 0.049(8) 0.052(9) 0.001(7) 0.004(7) -0.007(7) C11 0.050(9) 0.049(9) 0.056(9) -0.004(7) -0.002(7) 0.007(7) C12 0.046(8) 0.033(7) 0.047(9) -0.001(7) -0.005(7) -0.001(7) C13 0.045(8) 0.043(8) 0.040(8) 0.005(7) -0.003(7) -0.009(7) C14 0.044(11) 0.046(11) 0.066(13) 0.004(10) 0.003(10) -0.022(9) C15 0.041(8) 0.037(7) 0.032(8) 0.005(6) 0.006(7) 0.006(6) C16 0.032(7) 0.048(8) 0.035(8) 0.004(7) 0.005(6) 0.009(7) C17 0.037(7) 0.040(8) 0.042(8) 0.005(7) 0.000(7) 0.000(7) C18 0.044(8) 0.041(8) 0.037(8) -0.002(7) 0.003(7) -0.003(7) C19 0.039(7) 0.037(7) 0.034(8) 0.004(7) 0.000(7) 0.010(6) C20 0.033(7) 0.036(8) 0.037(8) -0.006(7) 0.002(6) 0.001(6) C21 0.039(9) 0.041(10) 0.047(11) -0.011(9) -0.003(9) 0.000(8) P1 0.029(2) 0.040(3) 0.042(3) 0.001(2) -0.001(2) -0.001(2) I1 0.0314(6) 0.0522(7) 0.0407(7) 0.0020(6) -0.0018(5) 0.0005(6) I2 0.0334(6) 0.0456(7) 0.0399(7) 0.0016(6) 0.0001(5) -0.0010(5) I3 0.0332(6) 0.0420(7) 0.0407(7) 0.0023(5) 0.0011(5) 0.0007(5) I4 0.0466(7) 0.0475(7) 0.0412(7) 0.0031(6) 0.0001(6) 0.0005(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.41(3) . ? C1 C6 1.45(3) . ? C1 P1 1.805(18) . ? C2 C3 1.38(3) . ? C2 H2 0.95 . ? C3 C4 1.41(3) . ? C3 H3 0.95 . ? C4 C5 1.32(3) . ? C4 H4 0.95 . ? C5 C6 1.42(3) . ? C5 H5 0.95 . ? C6 C7 1.48(3) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C9 1.38(3) . ? C8 C13 1.43(3) . ? C8 P1 1.80(2) . ? C9 C10 1.39(3) . ? C9 H9 0.95 . ? C10 C11 1.40(3) . ? C10 H10 0.95 . ? C11 C12 1.37(3) . ? C11 H11 0.95 . ? C12 C13 1.40(3) . ? C12 H12 0.95 . ? C13 C14 1.52(3) . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 C16 1.37(3) . ? C15 C20 1.47(3) . ? C15 P1 1.818(19) . ? C16 C17 1.34(3) . ? C16 H16 0.95 . ? C17 C18 1.38(3) . ? C17 H17 0.95 . ? C18 C19 1.40(3) . ? C18 H18 0.95 . ? C19 C20 1.39(3) . ? C19 H19 0.95 . ? C20 C21 1.51(3) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? P1 I1 2.429(5) . ? I2 I3 2.9839(18) . ? I3 I4 2.8539(18) . ? 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 C2 C1 C6 120.8(17) . . ? C2 C1 P1 118.6(14) . . ? C6 C1 P1 120.5(14) . . ? C3 C2 C1 119.2(18) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 121(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 123(2) . . ? C4 C5 H5 118.3 . . ? C6 C5 H5 118.3 . . ? C5 C6 C1 115.4(19) . . ? C5 C6 C7 119(2) . . ? C1 C6 C7 126(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 121.0(19) . . ? C9 C8 P1 117.7(15) . . ? C13 C8 P1 121.2(16) . . ? C8 C9 C10 121(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 119(2) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 120(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 124(2) . . ? C11 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C12 C13 C8 115.8(19) . . ? C12 C13 C14 119.7(19) . . ? C8 C13 C14 124(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 119.5(17) . . ? C16 C15 P1 122.9(15) . . ? C20 C15 P1 117.2(14) . . ? C17 C16 C15 123.6(19) . . ? C17 C16 H16 118.2 . . ? C15 C16 H16 118.2 . . ? C16 C17 C18 117.6(19) . . ? C16 C17 H17 121.2 . . ? C18 C17 H17 121.2 . . ? C17 C18 C19 123(2) . . ? C17 C18 H18 118.6 . . ? C19 C18 H18 118.6 . . ? C20 C19 C18 119.9(18) . . ? C20 C19 H19 120 . . ? C18 C19 H19 120 . . ? C19 C20 C15 116.5(17) . . ? C19 C20 C21 118.8(18) . . ? C15 C20 C21 124.6(18) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C8 P1 C1 115.1(9) . . ? C8 P1 C15 112.1(9) . . ? C1 P1 C15 107.7(9) . . ? C8 P1 I1 108.3(7) . . ? C1 P1 I1 107.4(6) . . ? C15 P1 I1 105.8(7) . . ? I4 I3 I2 177.89(6) . . ? # END of CIF # Attachment '- Compound2.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-07-07 at 19:00:10 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : robin dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_robin2 _database_code_depnum_ccdc_archive 'CCDC 865499' #TrackingRef '- Compound2.cif' _audit_creation_date 2010-07-07T19:00:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 I4 P1' _chemical_formula_sum 'C21 H21 I4 P' _chemical_formula_weight 811.78 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 13.2712(5) _cell_length_b 12.1324(4) _cell_length_c 14.9303(6) _cell_angle_alpha 90 _cell_angle_beta 91.8790(10) _cell_angle_gamma 90 _cell_volume 2402.66(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5770 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 2.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.4867 _exptl_absorpt_correction_T_max 0.6784 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.673754E-1 _diffrn_orient_matrix_ub_12 -0.369805E-1 _diffrn_orient_matrix_ub_13 -0.24528E-2 _diffrn_orient_matrix_ub_21 -0.35269E-2 _diffrn_orient_matrix_ub_22 0.90134E-2 _diffrn_orient_matrix_ub_23 -0.666052E-1 _diffrn_orient_matrix_ub_31 0.336455E-1 _diffrn_orient_matrix_ub_32 -0.731088E-1 _diffrn_orient_matrix_ub_33 -0.69709E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.081 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_number 27301 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 4205 _reflns_number_gt 2765 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. Electron density synthesis with coefficients Fo-Fc Highest peak 4.80 at 0.7969 0.0160 0.0888 [ 1.00 A from H7A ] Deepest hole -2.33 at 0.8226 0.7385 0.1459 [ 0.98 A from I4 ] ; _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^)+(0.0300P)^2^+167.6900P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4205 _refine_ls_number_parameters 238 _refine_ls_number_restraints 156 _refine_ls_R_factor_all 0.1371 _refine_ls_R_factor_gt 0.088 _refine_ls_wR_factor_ref 0.2038 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.14 _refine_ls_shift/su_max 0.03 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 4.802 _refine_diff_density_min -2.326 _refine_diff_density_rms 0.422 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.474 1.812 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6274(14) 0.5754(15) 0.7125(13) 0.033(4) Uani 1 1 d U . . C2 C 0.5412(14) 0.5663(16) 0.6538(14) 0.037(5) Uani 1 1 d U . . H2 H 0.5397 0.6001 0.5964 0.044 Uiso 1 1 calc R . . C3 C 0.4595(13) 0.5067(17) 0.6827(14) 0.039(5) Uani 1 1 d U . . C4 C 0.4595(15) 0.4513(14) 0.7600(14) 0.038(5) Uani 1 1 d U . . H4 H 0.4029 0.4087 0.7765 0.046 Uiso 1 1 calc R . . C5 C 0.5470(15) 0.4584(16) 0.8165(12) 0.036(5) Uani 1 1 d U . . H5 H 0.5485 0.4198 0.8719 0.043 Uiso 1 1 calc R . . C6 C 0.6326(14) 0.5211(16) 0.7935(12) 0.034(4) Uani 1 1 d U . . H6 H 0.6908 0.5254 0.8321 0.04 Uiso 1 1 calc R . . C7 C 0.3661(18) 0.497(2) 0.6190(14) 0.053(6) Uani 1 1 d U . . H7A H 0.3237 0.436 0.6384 0.08 Uiso 1 1 calc R . . H7B H 0.3878 0.483 0.5579 0.08 Uiso 1 1 calc R . . H7C H 0.3276 0.5658 0.6201 0.08 Uiso 1 1 calc R . . C8 C 0.7054(13) 0.7649(13) 0.6141(11) 0.024(4) Uani 1 1 d U . . C9 C 0.7722(14) 0.8105(15) 0.5529(15) 0.039(5) Uani 1 1 d U . . H9 H 0.8321 0.7712 0.5403 0.047 Uiso 1 1 calc R . . C10 C 0.7541(13) 0.9118(13) 0.5097(13) 0.029(4) Uani 1 1 d U . . C11 C 0.6665(13) 0.9650(13) 0.5279(10) 0.023(4) Uani 1 1 d U . . H11 H 0.6506 1.0322 0.498 0.028 Uiso 1 1 calc R . . C12 C 0.5986(14) 0.9223(18) 0.5905(13) 0.040(5) Uani 1 1 d U . . H12 H 0.539 0.9617 0.6035 0.048 Uiso 1 1 calc R . . C13 C 0.6194(12) 0.8232(16) 0.6322(11) 0.029(4) Uani 1 1 d U . . H13 H 0.5738 0.7947 0.6741 0.034 Uiso 1 1 calc R . . C14 C 0.8296(14) 0.9566(15) 0.4452(12) 0.032(4) Uani 1 1 d U . . H14A H 0.8122 0.9309 0.3844 0.048 Uiso 1 1 calc R . . H14B H 0.8973 0.9306 0.4629 0.048 Uiso 1 1 calc R . . H14C H 0.8283 1.0373 0.4465 0.048 Uiso 1 1 calc R . . C15 C 0.8256(13) 0.6741(14) 0.7627(13) 0.032(4) Uani 1 1 d U . . C16 C 0.9287(13) 0.6578(15) 0.7583(13) 0.032(4) Uani 1 1 d U . . H16 H 0.9546 0.6249 0.7062 0.038 Uiso 1 1 calc R . . C17 C 0.9961(14) 0.6884(16) 0.8285(14) 0.038(5) Uani 1 1 d U . . C18 C 0.9546(14) 0.7372(14) 0.9016(13) 0.034(4) Uani 1 1 d U . . H18 H 0.999 0.7602 0.9491 0.041 Uiso 1 1 calc R . . C19 C 0.8521(15) 0.7552(16) 0.9109(14) 0.041(5) Uani 1 1 d U . . H19 H 0.8282 0.7843 0.9653 0.049 Uiso 1 1 calc R . . C20 C 0.7853(13) 0.7309(16) 0.8413(13) 0.036(5) Uani 1 1 d U . . H20 H 0.716 0.7499 0.8437 0.044 Uiso 1 1 calc R . . C21 C 1.1078(16) 0.6687(16) 0.8189(13) 0.042(5) Uani 1 1 d U . . H21A H 1.1454 0.7063 0.8675 0.062 Uiso 1 1 calc R . . H21B H 1.1287 0.6977 0.7611 0.062 Uiso 1 1 calc R . . H21C H 1.1216 0.5894 0.8218 0.062 Uiso 1 1 calc R . . I1 I 0.81976(9) 0.51443(10) 0.57612(8) 0.0325(3) Uani 1 1 d U . . I2 I 0.92312(9) 0.28670(10) 0.47434(9) 0.0360(3) Uani 1 1 d U . . I3 I 1.04788(9) 0.30666(10) 0.64491(8) 0.0325(3) Uani 1 1 d U . . I4 I 1.16759(9) 0.31826(11) 0.80822(9) 0.0388(4) Uani 1 1 d U . . P1 P 0.7391(4) 0.6418(4) 0.6727(3) 0.0287(10) Uani 1 1 d U . . 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 0.031(10) 0.029(10) 0.042(11) -0.009(8) 0.014(8) 0.008(8) C2 0.028(10) 0.037(11) 0.046(12) 0.003(9) 0.005(9) 0.012(8) C3 0.017(9) 0.045(12) 0.055(13) -0.005(10) 0.001(8) -0.003(8) C4 0.041(12) 0.018(9) 0.056(13) -0.003(8) 0.009(10) 0.017(8) C5 0.047(12) 0.035(10) 0.026(10) -0.008(8) 0.003(8) 0.013(9) C6 0.032(10) 0.042(11) 0.027(10) -0.007(8) 0.000(8) -0.006(9) C7 0.071(15) 0.056(14) 0.034(11) -0.007(10) 0.022(11) 0.000(12) C8 0.031(9) 0.019(8) 0.022(9) 0.001(7) 0.005(7) -0.005(7) C9 0.021(10) 0.022(9) 0.075(15) -0.003(9) -0.005(9) 0.007(8) C10 0.025(9) 0.011(8) 0.050(11) 0.007(7) -0.004(8) -0.008(7) C11 0.038(10) 0.019(8) 0.014(8) -0.005(6) 0.008(7) 0.010(7) C12 0.026(10) 0.052(13) 0.042(12) -0.005(10) 0.004(8) -0.006(9) C13 0.018(9) 0.047(11) 0.019(9) 0.000(8) -0.013(7) 0.006(8) C14 0.032(10) 0.034(10) 0.031(10) 0.005(8) 0.006(8) -0.008(8) C15 0.027(10) 0.025(9) 0.042(11) 0.001(8) 0.006(8) 0.001(7) C16 0.024(9) 0.029(10) 0.044(11) 0.006(8) 0.004(8) -0.004(8) C17 0.030(10) 0.034(11) 0.051(12) 0.011(9) -0.004(9) -0.013(8) C18 0.030(10) 0.021(9) 0.051(12) -0.015(8) -0.008(9) -0.006(8) C19 0.039(12) 0.031(10) 0.053(13) -0.006(9) -0.004(9) 0.009(9) C20 0.018(9) 0.042(11) 0.049(12) -0.023(9) 0.001(8) 0.003(8) C21 0.054(13) 0.031(10) 0.040(11) 0.006(9) -0.007(9) -0.019(9) I1 0.0274(6) 0.0277(6) 0.0425(7) -0.0012(5) 0.0030(5) 0.0009(5) I2 0.0305(7) 0.0368(7) 0.0410(7) -0.0033(5) 0.0053(5) 0.0000(5) I3 0.0265(6) 0.0315(6) 0.0400(7) -0.0021(5) 0.0068(5) 0.0012(5) I4 0.0286(7) 0.0426(8) 0.0453(8) -0.0044(6) 0.0030(5) -0.0020(6) P1 0.026(2) 0.024(2) 0.036(3) -0.0004(19) 0.002(2) 0.0014(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C6 1.38(3) . ? C1 C2 1.42(3) . ? C1 P1 1.805(19) . ? C2 C3 1.38(3) . ? C2 H2 0.95 . ? C3 C4 1.34(3) . ? C3 C7 1.54(3) . ? C4 C5 1.42(3) . ? C4 H4 0.95 . ? C5 C6 1.42(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C13 1.38(2) . ? C8 C9 1.41(3) . ? C8 P1 1.781(17) . ? C9 C10 1.41(2) . ? C9 H9 0.95 . ? C10 C11 1.36(2) . ? C10 C14 1.51(2) . ? C11 C12 1.42(2) . ? C11 H11 0.95 . ? C12 C13 1.38(3) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 C16 1.39(2) . ? C15 C20 1.48(2) . ? C15 P1 1.782(19) . ? C16 C17 1.40(3) . ? C16 H16 0.95 . ? C17 C18 1.37(3) . ? C17 C21 1.51(3) . ? C18 C19 1.39(3) . ? C18 H18 0.95 . ? C19 C20 1.38(3) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? I1 P1 2.390(5) . ? I2 I3 3.0015(18) . ? I3 I4 2.8697(18) . ? 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 C6 C1 C2 121.4(17) . . ? C6 C1 P1 119.0(15) . . ? C2 C1 P1 119.0(15) . . ? C3 C2 C1 118.1(18) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C4 C3 C2 123.6(19) . . ? C4 C3 C7 118.2(18) . . ? C2 C3 C7 118.0(19) . . ? C3 C4 C5 117.5(19) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? C4 C5 C6 122.4(18) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C1 C6 C5 116.8(17) . . ? C1 C6 H6 121.6 . . ? C5 C6 H6 121.6 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 118.1(16) . . ? C13 C8 P1 122.0(13) . . ? C9 C8 P1 119.7(13) . . ? C10 C9 C8 122.6(17) . . ? C10 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? C11 C10 C9 117.1(16) . . ? C11 C10 C14 123.0(15) . . ? C9 C10 C14 119.9(17) . . ? C10 C11 C12 121.6(16) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C13 C12 C11 119.7(18) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C8 C13 C12 120.9(17) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 119.2(17) . . ? C16 C15 P1 123.1(14) . . ? C20 C15 P1 117.4(13) . . ? C15 C16 C17 122.2(18) . . ? C15 C16 H16 118.9 . . ? C17 C16 H16 118.9 . . ? C18 C17 C16 116.3(18) . . ? C18 C17 C21 124.3(18) . . ? C16 C17 C21 119.3(18) . . ? C17 C18 C19 124.6(18) . . ? C17 C18 H18 117.7 . . ? C19 C18 H18 117.7 . . ? C20 C19 C18 120.0(19) . . ? C20 C19 H19 120 . . ? C18 C19 H19 120 . . ? C19 C20 C15 117.3(17) . . ? C19 C20 H20 121.3 . . ? C15 C20 H20 121.3 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? I4 I3 I2 178.18(6) . . ? C15 P1 C8 109.4(8) . . ? C15 P1 C1 111.4(9) . . ? C8 P1 C1 109.9(8) . . ? C15 P1 I1 107.9(6) . . ? C8 P1 I1 110.8(6) . . ? C1 P1 I1 107.4(6) . . ? # END of CIF # Attachment '- Compound3.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-07-07 at 00:30:55 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_rob3 _database_code_depnum_ccdc_archive 'CCDC 865500' #TrackingRef '- Compound3.cif' _audit_creation_date 2010-07-07T00:30:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 I4 P1' _chemical_formula_sum 'C21 H21 I4 P' _chemical_formula_weight 811.78 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.4993(2) _cell_length_b 19.4335(5) _cell_length_c 12.6047(3) _cell_angle_alpha 90 _cell_angle_beta 105.104(2) _cell_angle_gamma 90 _cell_volume 2482.99(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5602 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 2.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.4007 _exptl_absorpt_correction_T_max 0.4611 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.577729E-1 _diffrn_orient_matrix_ub_12 -0.368744E-1 _diffrn_orient_matrix_ub_13 0.175174E-1 _diffrn_orient_matrix_ub_21 -0.516538E-1 _diffrn_orient_matrix_ub_22 0.355683E-1 _diffrn_orient_matrix_ub_23 0.283027E-1 _diffrn_orient_matrix_ub_31 -0.610452E-1 _diffrn_orient_matrix_ub_32 0.48014E-2 _diffrn_orient_matrix_ub_33 -0.751314E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_av_unetI/netI 0.0474 _diffrn_reflns_number 15682 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4864 _reflns_number_gt 3245 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0700P)^2^+26.0483P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4864 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1604 _refine_ls_goodness_of_fit_ref 1.247 _refine_ls_restrained_S_all 1.247 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 3.092 _refine_diff_density_min -1.792 _refine_diff_density_rms 0.296 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.474 1.812 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6701(10) 0.1852(6) 0.2243(8) 0.034(2) Uani 1 1 d . . . C2 C 0.6993(12) 0.1149(6) 0.2341(9) 0.039(3) Uani 1 1 d . . . H2 H 0.6485 0.0848 0.2662 0.047 Uiso 1 1 calc R . . C3 C 0.8049(12) 0.0889(6) 0.1959(10) 0.042(3) Uani 1 1 d . . . H3 H 0.8247 0.0412 0.2027 0.051 Uiso 1 1 calc R . . C4 C 0.8794(11) 0.1316(6) 0.1492(9) 0.038(3) Uani 1 1 d . . . C5 C 0.8488(11) 0.2006(7) 0.1396(9) 0.040(3) Uani 1 1 d . . . H5 H 0.901 0.2304 0.1084 0.048 Uiso 1 1 calc R . . C6 C 0.7456(11) 0.2276(6) 0.1736(9) 0.038(3) Uani 1 1 d . . . H6 H 0.725 0.2751 0.163 0.045 Uiso 1 1 calc R . . C7 C 0.9943(12) 0.1037(8) 0.1113(11) 0.051(3) Uani 1 1 d . . . H7A H 1.0262 0.0613 0.1514 0.077 Uiso 1 1 calc R . . H7B H 1.0655 0.1378 0.1256 0.077 Uiso 1 1 calc R . . H7C H 0.9659 0.094 0.0324 0.077 Uiso 1 1 calc R . . C8 C 0.4972(11) 0.1648(5) 0.3701(8) 0.033(2) Uani 1 1 d . . . C9 C 0.3685(11) 0.1388(6) 0.3526(9) 0.037(3) Uani 1 1 d . . . H9 H 0.3035 0.149 0.2866 0.045 Uiso 1 1 calc R . . C10 C 0.3370(12) 0.0976(6) 0.4334(10) 0.043(3) Uani 1 1 d . . . H10 H 0.2492 0.0812 0.4225 0.052 Uiso 1 1 calc R . . C11 C 0.4312(11) 0.0801(6) 0.5290(9) 0.038(3) Uani 1 1 d . . . C12 C 0.5599(11) 0.1060(6) 0.5438(9) 0.038(3) Uani 1 1 d . . . H12 H 0.6253 0.0957 0.6096 0.046 Uiso 1 1 calc R . . C13 C 0.5919(11) 0.1453(6) 0.4658(8) 0.034(2) Uani 1 1 d . . . H13 H 0.6807 0.1599 0.4762 0.041 Uiso 1 1 calc R . . C14 C 0.3968(13) 0.0380(6) 0.6162(9) 0.042(3) Uani 1 1 d . . . H14A H 0.3372 0.0641 0.6493 0.062 Uiso 1 1 calc R . . H14B H 0.4774 0.0265 0.6729 0.062 Uiso 1 1 calc R . . H14C H 0.3531 -0.0045 0.5838 0.062 Uiso 1 1 calc R . . C15 C 0.3951(10) 0.2320(5) 0.1578(8) 0.032(2) Uani 1 1 d . . . C16 C 0.2972(12) 0.2799(6) 0.1642(9) 0.042(3) Uani 1 1 d . . . H16 H 0.3078 0.3079 0.2278 0.05 Uiso 1 1 calc R . . C17 C 0.1874(12) 0.2863(7) 0.0793(11) 0.049(3) Uani 1 1 d . . . H17 H 0.1224 0.3193 0.084 0.059 Uiso 1 1 calc R . . C18 C 0.1680(12) 0.2453(7) -0.0149(10) 0.049(3) Uani 1 1 d . . . C19 C 0.2648(13) 0.1973(7) -0.0204(9) 0.051(3) Uani 1 1 d . . . H19 H 0.2532 0.169 -0.0837 0.061 Uiso 1 1 calc R . . C20 C 0.3757(12) 0.1905(6) 0.0635(8) 0.036(3) Uani 1 1 d . . . H20 H 0.4405 0.1575 0.0584 0.043 Uiso 1 1 calc R . . C21 C 0.0427(15) 0.2525(9) -0.1072(12) 0.069(4) Uani 1 1 d . . . H21A H 0.0536 0.2898 -0.1565 0.104 Uiso 1 1 calc R . . H21B H -0.0315 0.2631 -0.0762 0.104 Uiso 1 1 calc R . . H21C H 0.0252 0.2093 -0.1485 0.104 Uiso 1 1 calc R . . I1 I 0.60761(8) 0.33009(4) 0.34943(6) 0.0405(2) Uani 1 1 d . . . I2 I 0.71382(8) 0.49926(4) 0.39275(7) 0.0479(3) Uani 1 1 d . . . I3 I 0.5 0.5 0.5 0.0400(3) Uani 1 2 d S . . I4 I 0 0 0.5 0.0553(4) Uani 1 2 d S . . I5 I -0.05326(10) 0.07860(6) 0.68207(9) 0.0673(3) Uani 1 1 d . . . P1 P 0.5369(3) 0.21878(14) 0.2704(2) 0.0314(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 C1 0.027(5) 0.046(7) 0.027(5) 0.004(5) 0.007(4) -0.004(5) C2 0.042(7) 0.032(6) 0.046(6) -0.004(5) 0.017(5) 0.002(5) C3 0.042(7) 0.037(7) 0.054(7) 0.007(5) 0.022(6) 0.006(5) C4 0.036(6) 0.034(6) 0.046(6) -0.002(5) 0.012(5) 0.001(5) C5 0.027(6) 0.058(8) 0.035(6) -0.002(5) 0.009(4) -0.007(5) C6 0.038(6) 0.030(6) 0.040(6) 0.005(5) 0.003(5) -0.006(5) C7 0.039(7) 0.068(9) 0.052(7) -0.006(6) 0.021(6) 0.015(6) C8 0.038(6) 0.030(6) 0.035(5) 0.002(4) 0.016(5) 0.002(5) C9 0.031(6) 0.038(6) 0.041(6) 0.002(5) 0.006(5) -0.004(5) C10 0.039(7) 0.044(7) 0.051(7) -0.004(6) 0.020(5) -0.008(5) C11 0.039(6) 0.037(6) 0.042(6) -0.003(5) 0.018(5) 0.001(5) C12 0.039(6) 0.038(6) 0.038(6) 0.004(5) 0.010(5) 0.001(5) C13 0.030(6) 0.040(6) 0.031(5) 0.005(5) 0.008(4) -0.002(5) C14 0.053(7) 0.034(6) 0.041(6) 0.011(5) 0.019(5) 0.000(5) C15 0.029(5) 0.031(6) 0.036(5) 0.005(4) 0.008(4) 0.005(5) C16 0.042(7) 0.046(7) 0.037(6) -0.006(5) 0.011(5) -0.001(6) C17 0.037(7) 0.054(8) 0.063(8) 0.009(6) 0.023(6) 0.014(6) C18 0.040(7) 0.059(8) 0.043(7) 0.006(6) 0.000(5) 0.007(6) C19 0.060(8) 0.063(9) 0.026(6) 0.015(6) 0.004(5) 0.014(7) C20 0.047(7) 0.034(6) 0.028(5) 0.007(4) 0.012(5) 0.007(5) C21 0.055(9) 0.074(11) 0.064(9) -0.006(8) -0.009(7) 0.006(8) I1 0.0468(5) 0.0350(4) 0.0407(4) -0.0046(3) 0.0131(3) -0.0029(3) I2 0.0469(5) 0.0398(5) 0.0631(5) -0.0047(4) 0.0250(4) -0.0086(4) I3 0.0400(6) 0.0319(6) 0.0486(6) 0.0005(4) 0.0125(5) -0.0035(4) I4 0.0319(6) 0.0562(8) 0.0763(9) 0.0180(6) 0.0116(5) -0.0046(5) I5 0.0535(6) 0.0639(7) 0.0883(7) 0.0141(5) 0.0252(5) 0.0022(5) P1 0.0331(14) 0.0310(15) 0.0310(13) -0.0022(11) 0.0099(11) -0.0025(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.400(16) . ? C1 C6 1.408(15) . ? C1 P1 1.772(11) . ? C2 C3 1.411(16) . ? C2 H2 0.95 . ? C3 C4 1.374(16) . ? C3 H3 0.95 . ? C4 C5 1.376(17) . ? C4 C7 1.509(15) . ? C5 C6 1.370(16) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C13 1.401(15) . ? C8 C9 1.405(15) . ? C8 P1 1.768(11) . ? C9 C10 1.401(16) . ? C9 H9 0.95 . ? C10 C11 1.387(17) . ? C10 H10 0.95 . ? C11 C12 1.408(16) . ? C11 C14 1.489(15) . ? C12 C13 1.355(15) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 C16 1.406(16) . ? C15 C20 1.406(15) . ? C15 P1 1.788(10) . ? C16 C17 1.359(17) . ? C16 H16 0.95 . ? C17 C18 1.399(19) . ? C17 H17 0.95 . ? C18 C19 1.395(19) . ? C18 C21 1.519(17) . ? C19 C20 1.360(16) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? I1 P1 2.416(3) . ? I2 I3 2.9067(8) . ? I3 I2 2.9067(8) 3_666 ? I4 I5 2.9294(12) 3_556 ? I4 I5 2.9294(12) . ? 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 C2 C1 C6 118.4(10) . . ? C2 C1 P1 120.3(8) . . ? C6 C1 P1 121.3(9) . . ? C1 C2 C3 119.5(11) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 121.1(11) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.7(11) . . ? C3 C4 C7 120.7(11) . . ? C5 C4 C7 120.6(11) . . ? C6 C5 C4 122.1(11) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C1 120.2(11) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 118.3(10) . . ? C13 C8 P1 121.8(8) . . ? C9 C8 P1 119.8(8) . . ? C10 C9 C8 119.4(10) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11 C10 C9 121.4(11) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 118.1(10) . . ? C10 C11 C14 121.4(11) . . ? C12 C11 C14 120.5(11) . . ? C13 C12 C11 121.1(11) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C8 121.5(10) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.8(10) . . ? C16 C15 P1 121.3(8) . . ? C20 C15 P1 119.8(8) . . ? C17 C16 C15 119.8(11) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 121.5(12) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C19 C18 C17 118.4(11) . . ? C19 C18 C21 121.4(12) . . ? C17 C18 C21 120.2(12) . . ? C20 C19 C18 120.9(12) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C15 120.5(11) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? I2 I3 I2 180 3_666 . ? I5 I4 I5 180 3_556 . ? C8 P1 C1 111.5(5) . . ? C8 P1 C15 110.3(5) . . ? C1 P1 C15 110.9(5) . . ? C8 P1 I1 110.0(4) . . ? C1 P1 I1 106.3(4) . . ? C15 P1 I1 107.6(4) . . ? # END of CIF # Attachment '- Compound5.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2012-04-05 at 10:39:17 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : shelxl dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_4 _database_code_depnum_ccdc_archive 'CCDC 865501' #TrackingRef '- Compound5.cif' _audit_creation_date 2012-04-05T10:39:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_moiety 'C21 H21 As1 I4' _chemical_formula_sum 'C21 H21 As I4' _chemical_formula_weight 855.73 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.5855(2) _cell_length_b 19.5733(3) _cell_length_c 12.6174(2) _cell_angle_alpha 90 _cell_angle_beta 104.9790(10) _cell_angle_gamma 90 _cell_volume 2525.41(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5621 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 2.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.24 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.746 _exptl_absorpt_correction_T_max 0.985 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.336085E-1 _diffrn_orient_matrix_ub_12 0.00056 _diffrn_orient_matrix_ub_13 -0.671352E-1 _diffrn_orient_matrix_ub_21 -0.918027E-1 _diffrn_orient_matrix_ub_22 -0.11551E-2 _diffrn_orient_matrix_ub_23 -0.471582E-1 _diffrn_orient_matrix_ub_31 -0.24447E-2 _diffrn_orient_matrix_ub_32 0.510739E-1 _diffrn_orient_matrix_ub_33 -0.3305E-3 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_unetI/netI 0.0528 _diffrn_reflns_number 10969 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 5765 _reflns_number_gt 4179 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0669P)^2^+13.7167P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5765 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.075 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.235 _refine_diff_density_min -1.694 _refine_diff_density_rms 0.229 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.05 2.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.474 1.812 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3825(7) 0.2683(4) 0.6479(6) 0.0313(15) Uani 1 1 d . . . C2 C 0.2880(8) 0.2204(4) 0.6558(7) 0.0406(18) Uani 1 1 d . . . H2 H 0.2993 0.1931 0.7179 0.049 Uiso 1 1 calc R . . C3 C 0.1766(9) 0.2140(5) 0.5696(7) 0.046(2) Uani 1 1 d . . . H3 H 0.1133 0.1819 0.5739 0.055 Uiso 1 1 calc R . . C4 C 0.1590(8) 0.2543(5) 0.4781(7) 0.0447(19) Uani 1 1 d . . . C5 C 0.2527(9) 0.3021(5) 0.4710(7) 0.046(2) Uani 1 1 d . . . H5 H 0.2397 0.3296 0.4089 0.055 Uiso 1 1 calc R . . C6 C 0.3657(8) 0.3097(4) 0.5550(6) 0.0332(16) Uani 1 1 d . . . H6 H 0.4289 0.3415 0.5497 0.04 Uiso 1 1 calc R . . C7 C 0.0376(10) 0.2456(7) 0.3839(9) 0.068(3) Uani 1 1 d . . . H7A H 0.0348 0.1999 0.3558 0.101 Uiso 1 1 calc R . . H7B H 0.0402 0.2775 0.3268 0.101 Uiso 1 1 calc R . . H7C H -0.0388 0.2539 0.4096 0.101 Uiso 1 1 calc R . . C8 C 0.6752(7) 0.3176(4) 0.7156(6) 0.0326(15) Uani 1 1 d . . . C9 C 0.7043(8) 0.3867(4) 0.7270(7) 0.0399(18) Uani 1 1 d . . . H9 H 0.6546 0.4158 0.7583 0.048 Uiso 1 1 calc R . . C10 C 0.8077(9) 0.4116(5) 0.6914(8) 0.048(2) Uani 1 1 d . . . H10 H 0.8296 0.4576 0.7017 0.058 Uiso 1 1 calc R . . C11 C 0.8808(8) 0.3696(5) 0.6402(7) 0.0426(19) Uani 1 1 d . . . C12 C 0.8506(8) 0.3007(5) 0.6302(6) 0.0413(19) Uani 1 1 d . . . H12 H 0.8997 0.2718 0.5979 0.05 Uiso 1 1 calc R . . C13 C 0.7494(7) 0.2743(4) 0.6670(6) 0.0321(15) Uani 1 1 d . . . H13 H 0.7302 0.2279 0.6596 0.039 Uiso 1 1 calc R . . C14 C 0.9945(9) 0.3969(5) 0.6036(10) 0.059(3) Uani 1 1 d . . . H14A H 1.0639 0.3639 0.6188 0.089 Uiso 1 1 calc R . . H14B H 1.0246 0.4385 0.6423 0.089 Uiso 1 1 calc R . . H14C H 0.9681 0.4059 0.5262 0.089 Uiso 1 1 calc R . . C15 C 0.4934(7) 0.3391(4) 0.8734(6) 0.0306(15) Uani 1 1 d . . . C16 C 0.5890(7) 0.3577(4) 0.9664(6) 0.0342(16) Uani 1 1 d . . . H16 H 0.6746 0.3427 0.976 0.041 Uiso 1 1 calc R . . C17 C 0.5568(8) 0.3986(4) 1.0448(6) 0.0353(16) Uani 1 1 d . . . H17 H 0.6211 0.4113 1.107 0.042 Uiso 1 1 calc R . . C18 C 0.4276(8) 0.4209(4) 1.0310(6) 0.0351(16) Uani 1 1 d . . . C19 C 0.3348(8) 0.4032(4) 0.9372(6) 0.0373(17) Uani 1 1 d . . . H19 H 0.2495 0.4189 0.9268 0.045 Uiso 1 1 calc R . . C20 C 0.3659(8) 0.3621(4) 0.8574(7) 0.0394(17) Uani 1 1 d . . . H20 H 0.3021 0.3502 0.7943 0.047 Uiso 1 1 calc R . . C21 C 0.3944(8) 0.4641(4) 1.1195(7) 0.0415(18) Uani 1 1 d . . . H21A H 0.3273 0.4963 1.0865 0.062 Uiso 1 1 calc R . . H21B H 0.471 0.4882 1.1591 0.062 Uiso 1 1 calc R . . H21C H 0.3638 0.4351 1.1691 0.062 Uiso 1 1 calc R . . As1 As 0.53496(7) 0.28064(4) 0.76658(6) 0.03062(18) Uani 1 1 d . . . I1 I 0.60944(5) 0.16486(3) 0.84451(4) 0.03770(16) Uani 1 1 d . . . I2 I 0.71002(6) -0.00017(3) 0.89031(5) 0.04621(18) Uani 1 1 d . . . I3 I 0.5 0 1 0.03871(19) Uani 1 2 d S . . I4 I 1 0.5 1 0.0535(2) Uani 1 2 d S . . I5 I 1.05666(7) 0.57825(4) 0.81981(7) 0.0669(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 0.036(4) 0.026(4) 0.036(4) -0.003(3) 0.017(3) -0.005(3) C2 0.044(4) 0.036(4) 0.042(4) 0.006(4) 0.011(4) -0.001(4) C3 0.046(5) 0.037(5) 0.056(5) -0.005(4) 0.018(4) -0.009(4) C4 0.044(5) 0.042(5) 0.047(5) -0.011(4) 0.010(4) -0.005(4) C5 0.063(6) 0.044(5) 0.035(4) 0.002(4) 0.018(4) -0.003(4) C6 0.044(4) 0.025(4) 0.033(4) -0.004(3) 0.014(3) -0.005(3) C7 0.054(6) 0.085(8) 0.054(6) -0.005(6) -0.003(5) -0.017(6) C8 0.032(4) 0.033(4) 0.033(4) 0.000(3) 0.010(3) -0.002(3) C9 0.042(4) 0.031(4) 0.051(4) -0.002(4) 0.019(4) 0.001(3) C10 0.043(5) 0.043(5) 0.062(5) -0.003(4) 0.021(4) -0.009(4) C11 0.030(4) 0.045(5) 0.057(5) 0.001(4) 0.019(4) -0.008(3) C12 0.032(4) 0.052(5) 0.041(4) 0.002(4) 0.013(3) 0.008(4) C13 0.040(4) 0.022(3) 0.036(4) -0.009(3) 0.014(3) -0.003(3) C14 0.044(5) 0.057(6) 0.086(7) 0.013(5) 0.033(5) -0.008(4) C15 0.039(4) 0.027(4) 0.028(3) 0.008(3) 0.013(3) 0.002(3) C16 0.032(4) 0.036(4) 0.035(4) 0.006(3) 0.010(3) 0.004(3) C17 0.043(4) 0.031(4) 0.036(4) 0.003(3) 0.016(3) -0.001(3) C18 0.036(4) 0.032(4) 0.039(4) -0.001(3) 0.013(3) -0.005(3) C19 0.036(4) 0.038(4) 0.042(4) -0.003(3) 0.017(3) 0.004(3) C20 0.040(4) 0.038(4) 0.041(4) -0.002(4) 0.012(3) 0.006(3) C21 0.046(5) 0.033(4) 0.046(4) -0.003(4) 0.014(4) 0.005(4) As1 0.0350(4) 0.0254(4) 0.0335(4) -0.0001(3) 0.0127(3) -0.0009(3) I1 0.0462(3) 0.0294(3) 0.0385(3) 0.0033(2) 0.0126(2) 0.0022(2) I2 0.0478(3) 0.0346(3) 0.0628(4) 0.0062(2) 0.0263(3) 0.0105(2) I3 0.0428(4) 0.0247(4) 0.0503(4) 0.0017(3) 0.0149(3) 0.0041(3) I4 0.0327(4) 0.0504(5) 0.0771(6) -0.0186(4) 0.0137(4) 0.0049(3) I5 0.0564(4) 0.0607(5) 0.0877(5) -0.0126(4) 0.0259(4) -0.0022(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.394(11) . ? C1 C6 1.397(10) . ? C1 As1 1.912(8) . ? C2 C3 1.388(12) . ? C2 H2 0.93 . ? C3 C4 1.370(13) . ? C3 H3 0.93 . ? C4 C5 1.385(12) . ? C4 C7 1.517(12) . ? C5 C6 1.386(12) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 C9 1.387(11) . ? C8 C13 1.399(10) . ? C8 As1 1.907(7) . ? C9 C10 1.376(11) . ? C9 H9 0.93 . ? C10 C11 1.396(12) . ? C10 H10 0.93 . ? C11 C12 1.384(13) . ? C11 C14 1.495(11) . ? C12 C13 1.374(11) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 C16 1.386(11) . ? C15 C20 1.387(11) . ? C15 As1 1.904(7) . ? C16 C17 1.382(11) . ? C16 H16 0.93 . ? C17 C18 1.403(11) . ? C17 H17 0.93 . ? C18 C19 1.373(11) . ? C18 C21 1.512(11) . ? C19 C20 1.394(11) . ? C19 H19 0.93 . ? C20 H20 0.93 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? As1 I1 2.5146(9) . ? I2 I3 2.9066(5) . ? I3 I2 2.9066(5) 3_657 ? I4 I5 2.9291(8) . ? I4 I5 2.9291(8) 3_767 ? 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 C2 C1 C6 120.8(7) . . ? C2 C1 As1 120.3(6) . . ? C6 C1 As1 118.8(5) . . ? C3 C2 C1 119.0(8) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 120.8(8) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.0(8) . . ? C3 C4 C7 119.9(9) . . ? C5 C4 C7 120.1(9) . . ? C4 C5 C6 120.9(8) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.5(7) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 120.1(7) . . ? C9 C8 As1 120.4(6) . . ? C13 C8 As1 119.5(6) . . ? C10 C9 C8 119.1(8) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 121.6(8) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 118.3(7) . . ? C12 C11 C14 120.3(8) . . ? C10 C11 C14 121.2(8) . . ? C13 C12 C11 121.1(7) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C8 119.7(7) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 120.5(7) . . ? C16 C15 As1 120.4(6) . . ? C20 C15 As1 119.1(6) . . ? C17 C16 C15 119.8(7) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.3(7) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 119.0(7) . . ? C19 C18 C21 121.8(7) . . ? C17 C18 C21 119.2(7) . . ? C18 C19 C20 121.3(8) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C15 C20 C19 119.0(8) . . ? C15 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 As1 C8 110.7(3) . . ? C15 As1 C1 109.1(3) . . ? C8 As1 C1 110.9(3) . . ? C15 As1 I1 111.8(2) . . ? C8 As1 I1 106.3(2) . . ? C1 As1 I1 108.0(2) . . ? I2 I3 I2 180 3_657 . ? I5 I4 I5 180 . 3_767 ? # END of CIF # Attachment '- Compound6.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-07-07 at 13:29:22 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : new dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_new6 _database_code_depnum_ccdc_archive 'CCDC 865502' #TrackingRef '- Compound6.cif' _audit_creation_date 2010-07-07T13:29:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H15 As1 I4' _chemical_formula_sum 'C18 H15 As I4' _chemical_formula_weight 813.7 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 12.2801(2) _cell_length_b 38.8869(9) _cell_length_c 9.13000(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4359.87(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5394 _cell_measurement_theta_min 2 _cell_measurement_theta_max 52 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.222 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.2654 _exptl_absorpt_correction_T_max 0.7141 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.537006E-1 _diffrn_orient_matrix_ub_12 0.154205E-1 _diffrn_orient_matrix_ub_13 0.218774E-1 _diffrn_orient_matrix_ub_21 0.899396E-1 _diffrn_orient_matrix_ub_22 -0.184662E-1 _diffrn_orient_matrix_ub_23 0.134678E-1 _diffrn_orient_matrix_ub_31 0.319916E-1 _diffrn_orient_matrix_ub_32 0.777997E-1 _diffrn_orient_matrix_ub_33 -0.11396E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.093 _diffrn_reflns_av_unetI/netI 0.0459 _diffrn_reflns_number 13398 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 4078 _reflns_number_gt 2709 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'DIRDIF99 (Beurskens et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0432P)^2^+193.9326P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4078 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1205 _refine_ls_R_factor_gt 0.079 _refine_ls_wR_factor_ref 0.1965 _refine_ls_wR_factor_gt 0.1669 _refine_ls_goodness_of_fit_ref 1.18 _refine_ls_restrained_S_all 1.18 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.517 _refine_diff_density_min -1.876 _refine_diff_density_rms 0.367 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.05 2.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.474 1.812 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4673(12) 0.0976(5) 0.4300(19) 0.042(4) Uani 1 1 d . . . C2 C 0.4525(14) 0.0941(5) 0.5767(19) 0.048(4) Uani 1 1 d . . . H2 H 0.4133 0.111 0.6303 0.057 Uiso 1 1 calc R . . C3 C 0.4967(15) 0.0645(4) 0.6499(17) 0.046(4) Uani 1 1 d . . . H3 H 0.4884 0.0616 0.7526 0.055 Uiso 1 1 calc R . . C4 C 0.5525(15) 0.0400(6) 0.566(2) 0.057(5) Uani 1 1 d . . . H4 H 0.5789 0.0195 0.6097 0.069 Uiso 1 1 calc R . . C5 C 0.5685(16) 0.0459(4) 0.420(2) 0.055(5) Uani 1 1 d . . . H5 H 0.6114 0.03 0.3662 0.066 Uiso 1 1 calc R . . C6 C 0.5251(12) 0.0740(4) 0.3476(16) 0.036(4) Uani 1 1 d . . . H6 H 0.5346 0.077 0.2452 0.044 Uiso 1 1 calc R . . C7 C 0.3491(14) 0.1235(4) 0.1450(18) 0.043(4) Uani 1 1 d . . . C8 C 0.3340(13) 0.0892(4) 0.1053(18) 0.041(4) Uani 1 1 d . . . H8 H 0.351 0.0713 0.1723 0.049 Uiso 1 1 calc R . . C9 C 0.2944(12) 0.0816(5) -0.0316(19) 0.045(4) Uani 1 1 d . . . H9 H 0.2866 0.0583 -0.0613 0.055 Uiso 1 1 calc R . . C10 C 0.2655(13) 0.1082(5) -0.1271(19) 0.046(4) Uani 1 1 d . . . H10 H 0.236 0.1026 -0.2203 0.055 Uiso 1 1 calc R . . C11 C 0.2789(14) 0.1434(5) -0.089(2) 0.052(5) Uani 1 1 d . . . H11 H 0.2586 0.1612 -0.1545 0.062 Uiso 1 1 calc R . . C12 C 0.3226(14) 0.1508(5) 0.048(2) 0.049(4) Uani 1 1 d . . . H12 H 0.3348 0.174 0.0762 0.059 Uiso 1 1 calc R . . C13 C 0.2812(13) 0.1511(4) 0.4470(16) 0.034(3) Uani 1 1 d . . . C14 C 0.2682(13) 0.1829(5) 0.5071(18) 0.043(4) Uani 1 1 d . . . H14 H 0.3252 0.1992 0.4953 0.052 Uiso 1 1 calc R . . C15 C 0.1783(14) 0.1926(4) 0.5829(18) 0.042(4) Uani 1 1 d . . . H15 H 0.172 0.2154 0.6193 0.051 Uiso 1 1 calc R . . C16 C 0.0963(14) 0.1692(5) 0.607(2) 0.050(4) Uani 1 1 d . . . H16 H 0.0344 0.1758 0.6622 0.06 Uiso 1 1 calc R . . C17 C 0.1023(16) 0.1357(5) 0.5499(17) 0.048(4) Uani 1 1 d . . . H17 H 0.0453 0.1196 0.5663 0.057 Uiso 1 1 calc R . . C18 C 0.1951(13) 0.1266(5) 0.4683(17) 0.041(4) Uani 1 1 d . . . H18 H 0.2009 0.1042 0.4273 0.049 Uiso 1 1 calc R . . As1 As 0.40159(13) 0.13620(4) 0.33381(18) 0.0385(4) Uani 1 1 d . . . I1 I 0.53501(9) 0.18502(3) 0.31500(12) 0.0433(3) Uani 1 1 d . . . I2 I 0.72317(13) 0.25 0.30400(19) 0.0478(4) Uani 1 2 d S . . I3 I 0.86033(14) 0.25 0.58504(19) 0.0481(4) Uani 1 2 d S . . I4 I 0.99036(14) 0.25 0.83870(18) 0.0506(4) Uani 1 2 d S . . I5 I 0 0 0.5 0.0464(4) Uani 1 2 d S . . I6 I 0.21751(11) 0.02927(3) 0.52673(18) 0.0631(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.024(8) 0.054(10) 0.048(10) 0.005(8) 0.003(7) 0.002(7) C2 0.047(10) 0.053(10) 0.044(10) -0.006(8) 0.017(8) -0.005(8) C3 0.068(12) 0.050(10) 0.019(7) -0.003(7) -0.005(7) -0.002(9) C4 0.035(10) 0.075(13) 0.061(12) 0.001(10) -0.005(9) 0.003(9) C5 0.058(12) 0.034(9) 0.075(13) 0.001(9) -0.016(10) 0.003(8) C6 0.034(8) 0.053(10) 0.022(7) -0.003(7) -0.008(6) 0.010(7) C7 0.038(9) 0.050(10) 0.042(9) 0.012(8) 0.006(7) 0.010(8) C8 0.036(9) 0.045(9) 0.043(9) -0.011(7) 0.004(7) 0.016(7) C9 0.028(8) 0.055(10) 0.053(10) -0.007(8) -0.012(7) 0.015(8) C10 0.031(9) 0.059(11) 0.047(10) -0.002(8) -0.006(7) 0.007(8) C11 0.035(9) 0.066(12) 0.055(11) 0.016(9) -0.001(8) 0.013(9) C12 0.041(10) 0.050(10) 0.056(11) -0.008(9) 0.013(8) -0.001(8) C13 0.039(8) 0.033(8) 0.032(8) -0.012(6) -0.001(7) 0.000(7) C14 0.027(8) 0.057(10) 0.045(9) 0.005(8) -0.010(7) 0.008(7) C15 0.048(10) 0.034(8) 0.045(9) -0.001(7) -0.003(8) 0.000(8) C16 0.040(10) 0.061(11) 0.050(10) -0.012(9) -0.003(8) -0.007(9) C17 0.062(12) 0.050(10) 0.032(8) 0.011(7) 0.003(8) 0.006(9) C18 0.035(9) 0.055(10) 0.034(8) 0.008(7) -0.010(7) -0.012(8) As1 0.0338(9) 0.0449(9) 0.0368(9) 0.0001(7) 0.0006(7) 0.0003(7) I1 0.0380(6) 0.0490(6) 0.0430(6) -0.0031(5) 0.0022(5) -0.0022(5) I2 0.0403(9) 0.0473(9) 0.0557(10) 0 -0.0023(7) 0 I3 0.0455(9) 0.0471(9) 0.0516(9) 0 0.0052(8) 0 I4 0.0520(10) 0.0562(10) 0.0434(9) 0 0.0062(7) 0 I5 0.0470(9) 0.0441(9) 0.0480(9) -0.0003(7) 0.0011(7) 0.0056(7) I6 0.0445(7) 0.0505(7) 0.0943(11) 0.0013(7) -0.0025(7) 0.0012(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.36(2) . ? C1 C6 1.38(2) . ? C1 As1 1.917(17) . ? C2 C3 1.44(2) . ? C2 H2 0.95 . ? C3 C4 1.40(3) . ? C3 H3 0.95 . ? C4 C5 1.36(3) . ? C4 H4 0.95 . ? C5 C6 1.39(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.39(2) . ? C7 C12 1.42(2) . ? C7 As1 1.905(17) . ? C8 C9 1.37(2) . ? C8 H8 0.95 . ? C9 C10 1.40(2) . ? C9 H9 0.95 . ? C10 C11 1.42(3) . ? C10 H10 0.95 . ? C11 C12 1.39(3) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 C14 1.36(2) . ? C13 C18 1.44(2) . ? C13 As1 1.895(15) . ? C14 C15 1.36(2) . ? C14 H14 0.95 . ? C15 C16 1.37(2) . ? C15 H15 0.95 . ? C16 C17 1.40(2) . ? C16 H16 0.95 . ? C17 C18 1.41(2) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? As1 I1 2.514(2) . ? I2 I3 3.069(2) . ? I3 I4 2.813(2) . ? I5 I6 2.9136(13) . ? I5 I6 2.9136(13) 5_556 ? 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 C2 C1 C6 122.6(16) . . ? C2 C1 As1 118.3(13) . . ? C6 C1 As1 119.1(12) . . ? C1 C2 C3 119.2(16) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 118.2(15) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C5 C4 C3 119.5(19) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 122.9(19) . . ? C4 C5 H5 118.6 . . ? C6 C5 H5 118.6 . . ? C1 C6 C5 117.5(16) . . ? C1 C6 H6 121.3 . . ? C5 C6 H6 121.3 . . ? C8 C7 C12 121.5(16) . . ? C8 C7 As1 121.8(12) . . ? C12 C7 As1 116.7(13) . . ? C9 C8 C7 119.4(16) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 119.8(17) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 122.0(16) . . ? C9 C10 H10 119 . . ? C11 C10 H10 119 . . ? C12 C11 C10 117.8(16) . . ? C12 C11 H11 121.1 . . ? C10 C11 H11 121.1 . . ? C11 C12 C7 119.6(17) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? C14 C13 C18 117.5(15) . . ? C14 C13 As1 126.0(13) . . ? C18 C13 As1 116.4(11) . . ? C15 C14 C13 123.5(17) . . ? C15 C14 H14 118.2 . . ? C13 C14 H14 118.2 . . ? C14 C15 C16 119.5(16) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 121.2(17) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C16 C17 C18 118.2(17) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? C17 C18 C13 120.0(16) . . ? C17 C18 H18 120 . . ? C13 C18 H18 120 . . ? C13 As1 C7 108.0(7) . . ? C13 As1 C1 108.5(7) . . ? C7 As1 C1 110.8(7) . . ? C13 As1 I1 108.4(5) . . ? C7 As1 I1 110.7(5) . . ? C1 As1 I1 110.4(5) . . ? I4 I3 I2 178.69(8) . . ? I6 I5 I6 180.00(5) . 5_556 ? # END of CIF # Attachment '- Compound7.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-07-06 at 14:01:37 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_rob7 _database_code_depnum_ccdc_archive 'CCDC 865503' #TrackingRef '- Compound7.cif' _audit_creation_date 2010-07-06T14:01:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 Br4 P1' _chemical_formula_sum 'C21 H21 Br4 P' _chemical_formula_weight 623.78 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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 10.1330(3) _cell_length_b 13.4817(5) _cell_length_c 16.1088(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2200.62(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2775 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.3496 _exptl_absorpt_correction_T_max 0.5252 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.258378E-1 _diffrn_orient_matrix_ub_12 -0.29484E-1 _diffrn_orient_matrix_ub_13 0.545951E-1 _diffrn_orient_matrix_ub_21 0.951929E-1 _diffrn_orient_matrix_ub_22 -0.57576E-2 _diffrn_orient_matrix_ub_23 0.156482E-1 _diffrn_orient_matrix_ub_31 -0.31512E-2 _diffrn_orient_matrix_ub_32 0.67819E-1 _diffrn_orient_matrix_ub_33 0.250634E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0950 _diffrn_reflns_av_unetI/netI 0.0723 _diffrn_reflns_number 44427 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 4999 _reflns_number_gt 4030 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0412P)^2^+23.5781P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4999 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(2) _refine_diff_density_max 1.198 _refine_diff_density_min -1.059 _refine_diff_density_rms 0.185 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.29 2.46 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7913(9) 0.6620(8) 0.6413(6) 0.022(2) Uani 1 1 d . . . C2 C 0.8449(9) 0.7546(8) 0.6213(6) 0.026(2) Uani 1 1 d . . . C3 C 0.7740(11) 0.8175(8) 0.5705(7) 0.030(2) Uani 1 1 d . . . H3 H 0.8107 0.88 0.5559 0.036 Uiso 1 1 calc R . . C4 C 0.6507(11) 0.7918(9) 0.5401(7) 0.032(2) Uani 1 1 d . . . H4 H 0.6048 0.8359 0.5043 0.039 Uiso 1 1 calc R . . C5 C 0.5946(11) 0.7025(9) 0.5618(7) 0.033(2) Uani 1 1 d . . . H5 H 0.5096 0.6851 0.5416 0.04 Uiso 1 1 calc R . . C6 C 0.6624(10) 0.6391(8) 0.6126(6) 0.027(2) Uani 1 1 d . . . H6 H 0.6224 0.5784 0.629 0.033 Uiso 1 1 calc R . . C7 C 0.9775(10) 0.7919(9) 0.6550(7) 0.033(3) Uani 1 1 d . . . H7A H 1.0001 0.8549 0.6282 0.05 Uiso 1 1 calc R . . H7B H 1.0463 0.7428 0.6431 0.05 Uiso 1 1 calc R . . H7C H 0.9708 0.8017 0.7151 0.05 Uiso 1 1 calc R . . C8 C 0.7739(8) 0.4682(7) 0.7333(6) 0.024(2) Uani 1 1 d . . . C9 C 0.7364(10) 0.3992(8) 0.6712(7) 0.027(2) Uani 1 1 d . . . C10 C 0.6745(10) 0.3117(10) 0.7006(9) 0.041(3) Uani 1 1 d . . . H10 H 0.6512 0.262 0.6615 0.05 Uiso 1 1 calc R . . C11 C 0.6467(11) 0.2955(9) 0.7823(8) 0.036(3) Uani 1 1 d . . . H11 H 0.6041 0.2359 0.7988 0.043 Uiso 1 1 calc R . . C12 C 0.6804(10) 0.3658(8) 0.8414(7) 0.028(2) Uani 1 1 d . . . H12 H 0.6605 0.3544 0.8983 0.033 Uiso 1 1 calc R . . C13 C 0.7429(9) 0.4519(8) 0.8179(6) 0.026(2) Uani 1 1 d . . . H13 H 0.7652 0.5004 0.8583 0.031 Uiso 1 1 calc R . . C14 C 0.7591(11) 0.4131(9) 0.5801(7) 0.038(3) Uani 1 1 d . . . H14A H 0.818 0.4698 0.5713 0.057 Uiso 1 1 calc R . . H14B H 0.6746 0.4255 0.5524 0.057 Uiso 1 1 calc R . . H14C H 0.7996 0.3532 0.557 0.057 Uiso 1 1 calc R . . C15 C 0.9126(9) 0.6383(7) 0.8073(6) 0.021(2) Uani 1 1 d . . . C16 C 0.8253(9) 0.7039(7) 0.8459(6) 0.022(2) Uani 1 1 d . . . C17 C 0.8666(11) 0.7480(8) 0.9202(7) 0.031(2) Uani 1 1 d . . . H17 H 0.8101 0.7938 0.9474 0.038 Uiso 1 1 calc R . . C18 C 0.9872(10) 0.7262(8) 0.9542(6) 0.028(2) Uani 1 1 d . . . H18 H 1.0124 0.7569 1.0048 0.033 Uiso 1 1 calc R . . C19 C 1.0732(10) 0.6601(8) 0.9160(7) 0.033(2) Uani 1 1 d . . . H19 H 1.1562 0.6443 0.9401 0.04 Uiso 1 1 calc R . . C20 C 1.0336(10) 0.6175(8) 0.8410(7) 0.028(2) Uani 1 1 d . . . H20 H 1.0916 0.5735 0.8129 0.034 Uiso 1 1 calc R . . C21 C 0.6865(9) 0.7264(8) 0.8148(7) 0.026(2) Uani 1 1 d . . . H21A H 0.6441 0.6647 0.7967 0.04 Uiso 1 1 calc R . . H21B H 0.6914 0.7726 0.7679 0.04 Uiso 1 1 calc R . . H21C H 0.6348 0.7564 0.8596 0.04 Uiso 1 1 calc R . . Br1 Br 1.05023(9) 0.52696(8) 0.65354(6) 0.0283(2) Uani 1 1 d . . . Br2 Br 1.36448(9) 0.48563(8) 0.60312(6) 0.0301(2) Uani 1 1 d . . . Br3 Br 1.39415(8) 0.51569(7) 0.76225(5) 0.01927(19) Uani 1 1 d . . . Br4 Br 1.42767(11) 0.55163(8) 0.91672(7) 0.0335(3) Uani 1 1 d . . . P1 P 0.8677(2) 0.57777(19) 0.71124(15) 0.0232(5) 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 0.022(5) 0.025(5) 0.021(5) -0.008(4) 0.001(4) 0.003(4) C2 0.017(5) 0.029(6) 0.033(6) -0.004(4) 0.002(4) 0.000(4) C3 0.036(6) 0.019(5) 0.034(6) 0.002(5) 0.011(5) 0.000(4) C4 0.033(6) 0.032(6) 0.032(6) 0.007(5) -0.011(5) 0.008(5) C5 0.027(6) 0.041(6) 0.031(6) -0.003(5) -0.001(5) 0.000(5) C6 0.024(5) 0.028(6) 0.029(5) 0.000(4) 0.001(4) 0.000(4) C7 0.027(6) 0.041(7) 0.032(6) -0.002(5) -0.002(5) -0.018(5) C8 0.019(4) 0.017(5) 0.036(5) -0.006(4) 0.009(4) -0.005(4) C9 0.023(5) 0.018(5) 0.039(6) -0.010(4) 0.005(4) 0.002(4) C10 0.020(5) 0.042(7) 0.063(8) -0.022(6) -0.005(5) 0.006(5) C11 0.023(5) 0.027(6) 0.057(8) 0.007(5) 0.002(5) -0.005(4) C12 0.027(5) 0.022(5) 0.034(6) 0.006(5) 0.003(5) 0.004(4) C13 0.021(5) 0.031(6) 0.027(5) -0.003(5) -0.002(4) 0.002(4) C14 0.034(6) 0.033(6) 0.047(7) -0.017(6) 0.000(5) 0.001(5) C15 0.014(4) 0.026(5) 0.024(5) 0.007(4) -0.001(4) -0.005(4) C16 0.020(5) 0.021(5) 0.025(5) 0.001(4) -0.002(4) 0.005(4) C17 0.031(5) 0.029(6) 0.034(6) 0.002(5) 0.002(5) -0.002(4) C18 0.034(6) 0.028(6) 0.022(5) -0.001(4) -0.006(4) -0.002(4) C19 0.019(5) 0.042(6) 0.039(6) -0.001(5) -0.006(5) -0.001(4) C20 0.022(5) 0.031(6) 0.031(5) 0.012(5) 0.003(4) 0.002(4) C21 0.014(5) 0.035(6) 0.031(5) -0.005(5) 0.002(4) 0.004(4) Br1 0.0202(4) 0.0359(6) 0.0289(5) -0.0038(5) 0.0019(4) 0.0033(4) Br2 0.0240(4) 0.0348(6) 0.0314(5) -0.0005(5) 0.0006(4) -0.0004(4) Br3 0.0149(4) 0.0199(4) 0.0230(4) -0.0007(4) -0.0006(3) 0.0011(3) Br4 0.0349(6) 0.0312(6) 0.0346(6) -0.0029(5) 0.0017(5) 0.0011(4) P1 0.0185(11) 0.0264(13) 0.0245(12) -0.0023(10) 0.0002(10) 0.0004(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.399(14) . ? C1 C6 1.419(14) . ? C1 P1 1.778(10) . ? C2 C3 1.381(15) . ? C2 C7 1.534(13) . ? C3 C4 1.386(16) . ? C3 H3 0.95 . ? C4 C5 1.377(16) . ? C4 H4 0.95 . ? C5 C6 1.369(15) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C13 1.415(14) . ? C8 C9 1.418(14) . ? C8 P1 1.792(9) . ? C9 C10 1.418(17) . ? C9 C14 1.497(16) . ? C10 C11 1.364(18) . ? C10 H10 0.95 . ? C11 C12 1.386(16) . ? C11 H11 0.95 . ? C12 C13 1.376(15) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 C20 1.370(13) . ? C15 C16 1.397(13) . ? C15 P1 1.807(10) . ? C16 C17 1.400(15) . ? C16 C21 1.524(13) . ? C17 C18 1.370(15) . ? C17 H17 0.95 . ? C18 C19 1.391(15) . ? C18 H18 0.95 . ? C19 C20 1.395(15) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? Br1 P1 2.180(3) . ? Br2 Br3 2.6126(13) . ? Br3 Br4 2.5576(13) . ? 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 C2 C1 C6 118.5(10) . . ? C2 C1 P1 123.1(8) . . ? C6 C1 P1 117.9(8) . . ? C3 C2 C1 118.9(9) . . ? C3 C2 C7 117.7(10) . . ? C1 C2 C7 123.4(10) . . ? C2 C3 C4 121.7(10) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 120.1(10) . . ? C5 C4 H4 120 . . ? C3 C4 H4 120 . . ? C6 C5 C4 119.4(10) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 121.3(10) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 121.2(9) . . ? C13 C8 P1 115.9(7) . . ? C9 C8 P1 122.8(8) . . ? C10 C9 C8 115.3(10) . . ? C10 C9 C14 120.0(10) . . ? C8 C9 C14 124.7(10) . . ? C11 C10 C9 123.2(11) . . ? C11 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? C10 C11 C12 120.2(11) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.1(10) . . ? C13 C12 H12 120 . . ? C11 C12 H12 120 . . ? C12 C13 C8 119.9(10) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 121.3(9) . . ? C20 C15 P1 118.2(8) . . ? C16 C15 P1 120.5(7) . . ? C15 C16 C17 117.4(9) . . ? C15 C16 C21 124.4(9) . . ? C17 C16 C21 118.2(9) . . ? C18 C17 C16 121.2(10) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 121.2(10) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C20 117.8(9) . . ? C18 C19 H19 121.1 . . ? C20 C19 H19 121.1 . . ? C15 C20 C19 121.1(10) . . ? C15 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Br4 Br3 Br2 177.74(5) . . ? C1 P1 C8 114.9(5) . . ? C1 P1 C15 111.4(5) . . ? C8 P1 C15 109.6(4) . . ? C1 P1 Br1 107.5(3) . . ? C8 P1 Br1 106.0(3) . . ? C15 P1 Br1 107.0(3) . . ? # END of CIF # Attachment '- Compound8.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-07-07 at 00:14:48 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : robin dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_robin8 _database_code_depnum_ccdc_archive 'CCDC 865504' #TrackingRef '- Compound8.cif' _audit_creation_date 2010-07-07T00:14:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 Br4 P1' _chemical_formula_sum 'C21 H21 Br4 P' _chemical_formula_weight 623.78 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6670(5) _cell_length_b 13.6882(12) _cell_length_c 17.9291(14) _cell_angle_alpha 88.702(4) _cell_angle_beta 83.271(2) _cell_angle_gamma 71.752(4) _cell_volume 2237.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6394 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.852 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.27 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.3545 _exptl_absorpt_correction_T_max 0.5939 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.109267 _diffrn_orient_matrix_ub_12 -0.235586E-1 _diffrn_orient_matrix_ub_13 -0.17747E-2 _diffrn_orient_matrix_ub_21 -0.9078E-2 _diffrn_orient_matrix_ub_22 0.226345E-1 _diffrn_orient_matrix_ub_23 0.53486E-1 _diffrn_orient_matrix_ub_31 -0.00203 _diffrn_orient_matrix_ub_32 -0.696515E-1 _diffrn_orient_matrix_ub_33 0.170581E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.115 _diffrn_reflns_av_unetI/netI 0.0994 _diffrn_reflns_number 20233 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.885 _diffrn_measured_fraction_theta_max 0.885 _reflns_number_total 7368 _reflns_number_gt 4605 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0427P)^2^+107.5901P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7368 _refine_ls_number_parameters 481 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1518 _refine_ls_R_factor_gt 0.0962 _refine_ls_wR_factor_ref 0.2411 _refine_ls_wR_factor_gt 0.215 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.927 _refine_diff_density_min -1.097 _refine_diff_density_rms 0.238 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.29 2.46 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5178(18) 0.6702(13) 0.2458(9) 0.030(4) Uani 1 1 d . . . C2 C 0.5444(19) 0.7510(13) 0.2862(10) 0.035(4) Uani 1 1 d . . . H2 H 0.4782 0.7825 0.3287 0.042 Uiso 1 1 calc R . . C3 C 0.6623(19) 0.7830(14) 0.2647(9) 0.036(4) Uani 1 1 d . . . C4 C 0.755(2) 0.7366(16) 0.2024(11) 0.047(5) Uani 1 1 d . . . H4 H 0.8387 0.7583 0.1875 0.057 Uiso 1 1 calc R . . C5 C 0.734(2) 0.6612(15) 0.1612(10) 0.039(4) Uani 1 1 d . . . H5 H 0.8009 0.6314 0.1184 0.047 Uiso 1 1 calc R . . C6 C 0.6130(19) 0.6288(14) 0.1832(10) 0.039(5) Uani 1 1 d . . . H6 H 0.5956 0.5772 0.1545 0.046 Uiso 1 1 calc R . . C7 C 0.694(2) 0.8644(15) 0.3069(11) 0.047(5) Uani 1 1 d . . . H7A H 0.604 0.9061 0.3365 0.07 Uiso 1 1 calc R . . H7B H 0.7312 0.9084 0.2714 0.07 Uiso 1 1 calc R . . H7C H 0.768 0.8323 0.3405 0.07 Uiso 1 1 calc R . . C8 C 0.4508(17) 0.5195(14) 0.3488(9) 0.032(4) Uani 1 1 d . . . C9 C 0.3751(18) 0.4525(14) 0.3721(10) 0.035(4) Uani 1 1 d . . . H9 H 0.2834 0.4595 0.3547 0.042 Uiso 1 1 calc R . . C10 C 0.434(2) 0.3729(14) 0.4220(10) 0.036(4) Uani 1 1 d . . . C11 C 0.5610(19) 0.3703(16) 0.4483(11) 0.044(5) Uani 1 1 d . . . H11 H 0.5967 0.3215 0.4856 0.053 Uiso 1 1 calc R . . C12 C 0.642(2) 0.4351(13) 0.4236(10) 0.035(4) Uani 1 1 d . . . H12 H 0.7337 0.4276 0.4409 0.042 Uiso 1 1 calc R . . C13 C 0.5839(18) 0.5117(14) 0.3727(10) 0.037(4) Uani 1 1 d . . . H13 H 0.6358 0.5578 0.3548 0.044 Uiso 1 1 calc R . . C14 C 0.350(2) 0.2972(14) 0.4501(12) 0.046(5) Uani 1 1 d . . . H14A H 0.4178 0.2268 0.447 0.069 Uiso 1 1 calc R . . H14B H 0.2714 0.3027 0.4189 0.069 Uiso 1 1 calc R . . H14C H 0.3076 0.3142 0.5024 0.069 Uiso 1 1 calc R . . C15 C 0.2279(18) 0.7246(13) 0.3303(9) 0.031(4) Uani 1 1 d . . . C16 C 0.168(2) 0.7143(14) 0.4031(10) 0.039(4) Uani 1 1 d . . . H16 H 0.2028 0.6521 0.4296 0.047 Uiso 1 1 calc R . . C17 C 0.055(2) 0.7981(15) 0.4366(10) 0.039(4) Uani 1 1 d . . . C18 C 0.0000(19) 0.8853(13) 0.3942(10) 0.035(4) Uani 1 1 d . . . H18 H -0.0786 0.9415 0.4163 0.042 Uiso 1 1 calc R . . C19 C 0.057(2) 0.8918(15) 0.3222(11) 0.045(5) Uani 1 1 d . . . H19 H 0.0184 0.9524 0.2946 0.054 Uiso 1 1 calc R . . C20 C 0.1736(19) 0.8083(12) 0.2878(10) 0.035(4) Uani 1 1 d . . . H20 H 0.2124 0.811 0.2368 0.042 Uiso 1 1 calc R . . C21 C -0.016(2) 0.7878(16) 0.5169(10) 0.054(6) Uani 1 1 d . . . H21A H -0.0333 0.8517 0.5453 0.082 Uiso 1 1 calc R . . H21B H 0.0499 0.7304 0.5418 0.082 Uiso 1 1 calc R . . H21C H -0.1096 0.7749 0.5145 0.082 Uiso 1 1 calc R . . C22 C 0.1857(18) 0.2301(13) 0.1753(10) 0.035(4) Uani 1 1 d . . . C23 C 0.1371(19) 0.2164(14) 0.1085(9) 0.036(4) Uani 1 1 d . . . H23 H 0.181 0.1533 0.0814 0.044 Uiso 1 1 calc R . . C24 C 0.0236(19) 0.2938(14) 0.0794(10) 0.039(4) Uani 1 1 d . . . C25 C -0.039(2) 0.3846(14) 0.1217(10) 0.040(4) Uani 1 1 d . . . H25 H -0.1168 0.4378 0.1039 0.048 Uiso 1 1 calc R . . C26 C 0.011(2) 0.3995(15) 0.1896(10) 0.047(5) Uani 1 1 d . . . H26 H -0.0309 0.4626 0.2169 0.057 Uiso 1 1 calc R . . C27 C 0.121(2) 0.3207(16) 0.2159(11) 0.045(5) Uani 1 1 d . . . H27 H 0.1524 0.3288 0.2629 0.054 Uiso 1 1 calc R . . C28 C -0.024(2) 0.2769(15) 0.0051(12) 0.051(5) Uani 1 1 d . . . H28A H 0.0626 0.244 -0.0304 0.077 Uiso 1 1 calc R . . H28B H -0.0791 0.3432 -0.0147 0.077 Uiso 1 1 calc R . . H28C H -0.0866 0.2324 0.0119 0.077 Uiso 1 1 calc R . . C29 C 0.426(2) 0.0309(13) 0.1439(9) 0.036(4) Uani 1 1 d . . . C30 C 0.347(2) -0.0384(15) 0.1280(10) 0.042(5) Uani 1 1 d . . . H30 H 0.2495 -0.0271 0.1502 0.05 Uiso 1 1 calc R . . C31 C 0.416(2) -0.1218(14) 0.0798(10) 0.037(4) Uani 1 1 d . . . C32 C 0.559(2) -0.1372(14) 0.0517(10) 0.042(5) Uani 1 1 d . . . H32 H 0.6082 -0.196 0.0207 0.05 Uiso 1 1 calc R . . C33 C 0.6357(19) -0.0706(14) 0.0663(9) 0.037(4) Uani 1 1 d . . . H33 H 0.7342 -0.083 0.0445 0.044 Uiso 1 1 calc R . . C34 C 0.567(2) 0.0132(13) 0.1128(9) 0.033(4) Uani 1 1 d . . . H34 H 0.619 0.0592 0.1232 0.04 Uiso 1 1 calc R . . C35 C 0.333(2) -0.1939(16) 0.0631(11) 0.048(5) Uani 1 1 d . . . H35A H 0.3071 -0.1832 0.0117 0.072 Uiso 1 1 calc R . . H35B H 0.244 -0.1801 0.0985 0.072 Uiso 1 1 calc R . . H35C H 0.3951 -0.2651 0.0682 0.072 Uiso 1 1 calc R . . C36 C 0.4759(19) 0.1985(14) 0.2213(11) 0.041(5) Uani 1 1 d . . . C37 C 0.5726(19) 0.1649(15) 0.2746(10) 0.039(5) Uani 1 1 d . . . H37 H 0.5609 0.1138 0.3094 0.047 Uiso 1 1 calc R . . C38 C 0.6887(19) 0.2065(14) 0.2772(10) 0.039(5) Uani 1 1 d . . . C39 C 0.701(2) 0.2791(16) 0.2264(11) 0.049(5) Uani 1 1 d . . . H39 H 0.7793 0.3073 0.228 0.059 Uiso 1 1 calc R . . C40 C 0.607(2) 0.3140(17) 0.1729(10) 0.048(5) Uani 1 1 d . . . H40 H 0.6199 0.3647 0.138 0.058 Uiso 1 1 calc R . . C41 C 0.492(2) 0.2724(15) 0.1713(11) 0.046(5) Uani 1 1 d . . . H41 H 0.4244 0.2958 0.1352 0.055 Uiso 1 1 calc R . . C42 C 0.797(2) 0.1656(16) 0.3316(11) 0.047(5) Uani 1 1 d . . . H42A H 0.895 0.1351 0.3041 0.07 Uiso 1 1 calc R . . H42B H 0.77 0.1129 0.3623 0.07 Uiso 1 1 calc R . . H42C H 0.7989 0.2217 0.3641 0.07 Uiso 1 1 calc R . . Br1 Br 0 0.5 0.5 0.0434(7) Uani 1 2 d S . . Br2 Br -0.0521(2) 0.55668(18) 0.36688(12) 0.0515(6) Uani 1 1 d . . . Br3 Br 0.5 0 0.5 0.0382(6) Uani 1 2 d S . . Br4 Br 0.6876(2) 0.08202(15) 0.53430(10) 0.0407(5) Uani 1 1 d . . . Br5 Br 1 0 0 0.0408(6) Uani 1 2 d S . . Br6 Br 0.9389(2) 0.0043(2) 0.14182(12) 0.0586(6) Uani 1 1 d . . . Br7 Br 0.5 0.5 0 0.0398(6) Uani 1 2 d S . . Br8 Br 0.2741(2) 0.44150(15) 0.02960(10) 0.0440(5) Uani 1 1 d . . . Br9 Br 0.2982(2) 0.55887(14) 0.19577(10) 0.0401(5) Uani 1 1 d . . . Br10 Br 0.2772(2) 0.07549(15) 0.31336(10) 0.0446(5) Uani 1 1 d . . . P1 P 0.3786(5) 0.6217(4) 0.2859(3) 0.0350(11) Uani 1 1 d . . . P2 P 0.3408(5) 0.1375(4) 0.2076(3) 0.0376(11) 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 0.031(10) 0.023(9) 0.032(9) 0.007(7) -0.008(8) -0.001(7) C2 0.030(10) 0.023(9) 0.047(11) 0.006(8) -0.011(8) 0.000(8) C3 0.026(10) 0.042(11) 0.035(10) 0.006(8) -0.011(8) -0.004(8) C4 0.036(12) 0.060(14) 0.051(12) 0.003(10) -0.010(9) -0.019(10) C5 0.035(11) 0.039(11) 0.037(10) -0.007(9) 0.012(8) -0.008(9) C6 0.034(11) 0.030(10) 0.039(10) -0.010(8) -0.008(8) 0.011(8) C7 0.047(12) 0.041(12) 0.058(12) 0.010(10) -0.019(10) -0.017(10) C8 0.019(9) 0.036(10) 0.040(10) -0.006(8) -0.007(7) -0.008(8) C9 0.012(8) 0.035(11) 0.048(11) -0.002(8) 0.004(7) 0.006(7) C10 0.038(11) 0.028(10) 0.039(10) 0.002(8) 0.001(8) -0.009(8) C11 0.027(10) 0.057(13) 0.044(11) -0.016(10) -0.002(8) -0.007(9) C12 0.041(11) 0.022(10) 0.047(10) 0.005(8) -0.012(9) -0.013(8) C13 0.019(9) 0.039(11) 0.050(11) -0.006(9) 0.003(8) -0.007(8) C14 0.040(12) 0.029(11) 0.073(14) 0.001(10) -0.011(10) -0.015(9) C15 0.027(9) 0.027(10) 0.039(10) -0.008(8) -0.012(8) -0.004(8) C16 0.043(12) 0.033(11) 0.040(10) 0.004(8) -0.017(9) -0.007(9) C17 0.038(11) 0.044(12) 0.034(10) 0.000(9) -0.003(8) -0.012(9) C18 0.029(10) 0.030(10) 0.041(10) -0.007(8) -0.010(8) -0.001(8) C19 0.034(11) 0.040(12) 0.052(12) -0.018(9) -0.008(9) 0.003(9) C20 0.035(10) 0.021(9) 0.041(10) 0.002(8) -0.012(8) 0.005(8) C21 0.059(14) 0.051(13) 0.045(12) -0.003(10) -0.024(10) 0.002(11) C22 0.026(10) 0.028(10) 0.042(10) 0.010(8) -0.008(8) 0.003(8) C23 0.035(11) 0.032(10) 0.034(9) -0.012(8) 0.009(8) -0.002(8) C24 0.026(10) 0.035(11) 0.049(11) -0.009(9) -0.001(8) -0.001(8) C25 0.040(11) 0.031(11) 0.051(11) 0.011(9) -0.007(9) -0.015(9) C26 0.040(12) 0.042(12) 0.043(11) -0.021(9) 0.006(9) 0.011(9) C27 0.034(11) 0.053(13) 0.049(11) -0.007(10) -0.011(9) -0.011(10) C28 0.040(12) 0.037(12) 0.080(15) 0.008(11) -0.028(11) -0.010(9) C29 0.052(12) 0.024(10) 0.025(9) -0.008(7) -0.011(8) 0.001(8) C30 0.037(11) 0.045(12) 0.044(11) -0.003(9) -0.010(9) -0.011(9) C31 0.035(11) 0.035(11) 0.041(10) 0.018(9) -0.013(8) -0.010(9) C32 0.040(12) 0.027(10) 0.047(11) 0.000(8) -0.018(9) 0.011(8) C33 0.028(10) 0.043(12) 0.033(9) -0.005(8) 0.009(8) -0.007(8) C34 0.039(11) 0.024(9) 0.028(9) 0.000(7) -0.002(8) 0.002(8) C35 0.046(12) 0.044(13) 0.060(13) -0.007(10) -0.002(10) -0.024(10) C36 0.029(10) 0.033(11) 0.053(11) -0.001(9) -0.012(9) 0.005(8) C37 0.030(10) 0.040(11) 0.035(10) -0.016(8) 0.003(8) 0.007(8) C38 0.031(10) 0.031(10) 0.044(11) -0.004(9) -0.014(8) 0.008(8) C39 0.044(12) 0.050(13) 0.056(12) -0.009(11) -0.007(10) -0.017(10) C40 0.056(14) 0.055(14) 0.037(10) -0.003(9) 0.001(9) -0.024(11) C41 0.047(12) 0.030(11) 0.056(12) -0.002(10) -0.006(10) -0.006(9) C42 0.038(11) 0.045(12) 0.051(12) -0.008(10) -0.003(9) -0.005(9) Br1 0.0343(15) 0.0421(16) 0.0542(16) -0.0092(13) -0.0046(12) -0.0121(12) Br2 0.0390(12) 0.0639(14) 0.0547(12) -0.0042(10) -0.0085(9) -0.0189(10) Br3 0.0441(16) 0.0322(14) 0.0350(13) -0.0025(11) -0.0063(11) -0.0066(12) Br4 0.0421(11) 0.0376(11) 0.0430(10) 0.0000(8) -0.0080(8) -0.0119(9) Br5 0.0311(14) 0.0381(15) 0.0521(16) 0.0036(12) -0.0084(12) -0.0081(12) Br6 0.0378(12) 0.0891(18) 0.0482(12) 0.0004(11) -0.0065(9) -0.0183(11) Br7 0.0485(17) 0.0308(14) 0.0355(13) -0.0005(11) -0.0072(12) -0.0050(12) Br8 0.0488(12) 0.0396(11) 0.0427(10) 0.0008(9) -0.0099(9) -0.0108(9) Br9 0.0406(11) 0.0385(11) 0.0406(10) -0.0057(8) -0.0087(8) -0.0096(8) Br10 0.0481(12) 0.0422(12) 0.0410(10) 0.0013(9) -0.0031(9) -0.0115(9) P1 0.036(3) 0.031(3) 0.036(2) -0.007(2) -0.007(2) -0.006(2) P2 0.035(3) 0.031(3) 0.043(3) -0.001(2) -0.008(2) -0.003(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C6 1.37(2) . ? C1 C2 1.44(2) . ? C1 P1 1.755(18) . ? C2 C3 1.36(3) . ? C2 H2 0.95 . ? C3 C4 1.38(3) . ? C3 C7 1.49(3) . ? C4 C5 1.36(3) . ? C4 H4 0.95 . ? C5 C6 1.39(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C9 1.37(2) . ? C8 C13 1.37(2) . ? C8 P1 1.793(18) . ? C9 C10 1.41(2) . ? C9 H9 0.95 . ? C10 C11 1.36(2) . ? C10 C14 1.55(3) . ? C11 C12 1.39(3) . ? C11 H11 0.95 . ? C12 C13 1.40(2) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 C20 1.36(2) . ? C15 C16 1.39(3) . ? C15 P1 1.799(17) . ? C16 C17 1.40(3) . ? C16 H16 0.95 . ? C17 C18 1.39(2) . ? C17 C21 1.54(3) . ? C18 C19 1.35(3) . ? C18 H18 0.95 . ? C19 C20 1.42(2) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 C23 1.37(2) . ? C22 C27 1.38(3) . ? C22 P2 1.781(16) . ? C23 C24 1.41(2) . ? C23 H23 0.95 . ? C24 C25 1.40(3) . ? C24 C28 1.50(3) . ? C25 C26 1.40(2) . ? C25 H25 0.95 . ? C26 C27 1.38(3) . ? C26 H26 0.95 . ? C27 H27 0.95 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C29 C34 1.37(3) . ? C29 C30 1.44(3) . ? C29 P2 1.793(16) . ? C30 C31 1.39(3) . ? C30 H30 0.95 . ? C31 C32 1.37(3) . ? C31 C35 1.51(2) . ? C32 C33 1.39(3) . ? C32 H32 0.95 . ? C33 C34 1.37(2) . ? C33 H33 0.95 . ? C34 H34 0.95 . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? C36 C41 1.37(3) . ? C36 C37 1.38(2) . ? C36 P2 1.80(2) . ? C37 C38 1.41(3) . ? C37 H37 0.95 . ? C38 C39 1.36(3) . ? C38 C42 1.49(2) . ? C39 C40 1.37(3) . ? C39 H39 0.95 . ? C40 C41 1.41(3) . ? C40 H40 0.95 . ? C41 H41 0.95 . ? C42 H42A 0.98 . ? C42 H42B 0.98 . ? C42 H42C 0.98 . ? Br1 Br2 2.551(2) 2_566 ? Br1 Br2 2.551(2) . ? Br3 Br4 2.5484(19) 2_656 ? Br3 Br4 2.5484(19) . ? Br5 Br6 2.540(2) 2_755 ? Br5 Br6 2.540(2) . ? Br7 Br8 2.548(2) 2_665 ? Br7 Br8 2.548(2) . ? Br9 P1 2.174(5) . ? Br10 P2 2.162(6) . ? 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 C6 C1 C2 117.9(17) . . ? C6 C1 P1 124.3(14) . . ? C2 C1 P1 117.5(13) . . ? C3 C2 C1 121.2(17) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 118.0(17) . . ? C2 C3 C7 122.1(17) . . ? C4 C3 C7 119.9(18) . . ? C5 C4 C3 123.4(19) . . ? C5 C4 H4 118.3 . . ? C3 C4 H4 118.3 . . ? C4 C5 C6 118.4(17) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C1 C6 C5 121.1(17) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 121.8(17) . . ? C9 C8 P1 120.9(12) . . ? C13 C8 P1 117.3(14) . . ? C8 C9 C10 119.9(16) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 117.4(17) . . ? C11 C10 C14 121.4(17) . . ? C9 C10 C14 121.1(16) . . ? C10 C11 C12 123.5(19) . . ? C10 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C13 118.1(17) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C8 C13 C12 119.1(17) . . ? C8 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 123.1(16) . . ? C20 C15 P1 116.6(14) . . ? C16 C15 P1 120.2(13) . . ? C15 C16 C17 118.2(17) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C18 C17 C16 119.1(17) . . ? C18 C17 C21 121.5(17) . . ? C16 C17 C21 119.2(17) . . ? C19 C18 C17 121.4(17) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 120.3(19) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 117.7(18) . . ? C15 C20 H20 121.2 . . ? C19 C20 H20 121.2 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 119.8(15) . . ? C23 C22 P2 121.3(13) . . ? C27 C22 P2 118.6(13) . . ? C22 C23 C24 121.4(16) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C25 C24 C23 117.2(16) . . ? C25 C24 C28 123.0(16) . . ? C23 C24 C28 119.8(16) . . ? C24 C25 C26 121.8(17) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C27 C26 C25 118.5(17) . . ? C27 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? C26 C27 C22 121.2(17) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C34 C29 C30 120.0(16) . . ? C34 C29 P2 119.8(14) . . ? C30 C29 P2 120.2(15) . . ? C31 C30 C29 119.3(18) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C32 C31 C30 118.2(18) . . ? C32 C31 C35 122.7(18) . . ? C30 C31 C35 119.1(17) . . ? C31 C32 C33 123.0(17) . . ? C31 C32 H32 118.5 . . ? C33 C32 H32 118.5 . . ? C34 C33 C32 119.2(17) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C29 C34 C33 120.3(18) . . ? C29 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C31 C35 H35A 109.5 . . ? C31 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C31 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C41 C36 C37 120.3(19) . . ? C41 C36 P2 117.4(14) . . ? C37 C36 P2 121.9(16) . . ? C36 C37 C38 119.9(19) . . ? C36 C37 H37 120 . . ? C38 C37 H37 120 . . ? C39 C38 C37 118.1(16) . . ? C39 C38 C42 122.1(19) . . ? C37 C38 C42 119.7(18) . . ? C38 C39 C40 123.3(19) . . ? C38 C39 H39 118.4 . . ? C40 C39 H39 118.4 . . ? C39 C40 C41 118(2) . . ? C39 C40 H40 121 . . ? C41 C40 H40 121 . . ? C36 C41 C40 120.4(19) . . ? C36 C41 H41 119.8 . . ? C40 C41 H41 119.8 . . ? C38 C42 H42A 109.5 . . ? C38 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C38 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? Br2 Br1 Br2 180.00(3) 2_566 . ? Br4 Br3 Br4 180.00(4) 2_656 . ? Br6 Br5 Br6 180.00(2) 2_755 . ? Br8 Br7 Br8 180 2_665 . ? C1 P1 C8 110.1(8) . . ? C1 P1 C15 109.8(8) . . ? C8 P1 C15 113.0(8) . . ? C1 P1 Br9 108.0(6) . . ? C8 P1 Br9 108.2(5) . . ? C15 P1 Br9 107.6(5) . . ? C22 P2 C29 113.6(8) . . ? C22 P2 C36 109.1(9) . . ? C29 P2 C36 107.8(9) . . ? C22 P2 Br10 110.2(6) . . ? C29 P2 Br10 107.2(6) . . ? C36 P2 Br10 108.8(7) . . ? # END of CIF # Attachment '- Compound9.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-02-28 at 03:52:05 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_rob9 _database_code_depnum_ccdc_archive 'CCDC 865505' #TrackingRef '- Compound9.cif' _audit_creation_date 2011-02-28T03:52:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 Br4 P1' _chemical_formula_sum 'C21 H21 Br4 P' _chemical_formula_weight 623.99 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.0287(4) _cell_length_b 18.4142(8) _cell_length_c 12.8713(7) _cell_angle_alpha 90 _cell_angle_beta 105.981(2) _cell_angle_gamma 90 _cell_volume 2285.09(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4051 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.4821 _exptl_absorpt_correction_T_max 0.5998 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.102534 _diffrn_orient_matrix_ub_12 0.1828E-2 _diffrn_orient_matrix_ub_13 0.334283E-1 _diffrn_orient_matrix_ub_21 -0.154577E-1 _diffrn_orient_matrix_ub_22 0.00339 _diffrn_orient_matrix_ub_23 0.733554E-1 _diffrn_orient_matrix_ub_31 0.24928E-2 _diffrn_orient_matrix_ub_32 -0.541692E-1 _diffrn_orient_matrix_ub_33 0.57188E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.093 _diffrn_reflns_av_unetI/netI 0.1344 _diffrn_reflns_number 19847 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 4224 _reflns_number_gt 2187 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0932P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4224 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1564 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1453 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.874 _refine_diff_density_min -1.529 _refine_diff_density_rms 0.213 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' 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 0.3315(10) 0.1759(6) 0.2914(8) 0.032(3) Uani 1 1 d . . . C2 C 0.2647(9) 0.2168(6) 0.3498(9) 0.032(3) Uani 1 1 d . . . H2 H 0.2896 0.2662 0.3655 0.039 Uiso 1 1 calc R . . C3 C 0.1607(10) 0.1856(6) 0.3858(8) 0.034(3) Uani 1 1 d . . . H3 H 0.1157 0.2142 0.4277 0.041 Uiso 1 1 calc R . . C4 C 0.1196(9) 0.1149(6) 0.3634(8) 0.032(3) Uani 1 1 d . . . C5 C 0.1858(11) 0.0743(6) 0.3019(9) 0.040(3) Uani 1 1 d . . . H5 H 0.1573 0.0257 0.2833 0.048 Uiso 1 1 calc R . . C6 C 0.2936(10) 0.1039(6) 0.2670(9) 0.034(3) Uani 1 1 d . . . H6 H 0.3408 0.0753 0.2269 0.041 Uiso 1 1 calc R . . C7 C 0.0062(10) 0.0808(7) 0.4020(9) 0.042(3) Uani 1 1 d . . . H7A H 0.0458 0.0591 0.4734 0.063 Uiso 1 1 calc R . . H7B H -0.0396 0.0431 0.3509 0.063 Uiso 1 1 calc R . . H7C H -0.0616 0.118 0.407 0.063 Uiso 1 1 calc R . . C8 C 0.5182(9) 0.1609(5) 0.1499(7) 0.025(2) Uani 1 1 d . . . C9 C 0.4188(9) 0.1478(6) 0.0547(8) 0.025(2) Uani 1 1 d . . . H9 H 0.3273 0.1655 0.0451 0.03 Uiso 1 1 calc R . . C10 C 0.4507(10) 0.1090(6) -0.0279(8) 0.027(2) Uani 1 1 d . . . H10 H 0.3805 0.0995 -0.0929 0.033 Uiso 1 1 calc R . . C11 C 0.5861(10) 0.0837(6) -0.0157(8) 0.031(3) Uani 1 1 d . . . C12 C 0.6822(11) 0.0942(6) 0.0832(8) 0.032(3) Uani 1 1 d . . . H12 H 0.7715 0.0729 0.096 0.039 Uiso 1 1 calc R . . C13 C 0.6516(9) 0.1352(6) 0.1644(8) 0.030(2) Uani 1 1 d . . . H13 H 0.7216 0.1454 0.2292 0.036 Uiso 1 1 calc R . . C14 C 0.6197(11) 0.0421(6) -0.1029(8) 0.035(3) Uani 1 1 d . . . H14A H 0.5338 0.0251 -0.1539 0.053 Uiso 1 1 calc R . . H14B H 0.6775 0.0003 -0.072 0.053 Uiso 1 1 calc R . . H14C H 0.6702 0.0733 -0.1408 0.053 Uiso 1 1 calc R . . C15 C 0.6213(10) 0.2263(6) 0.3656(8) 0.032(3) Uani 1 1 d . . . C16 C 0.6299(10) 0.1850(6) 0.4589(8) 0.029(2) Uani 1 1 d . . . H16 H 0.5559 0.1537 0.4627 0.035 Uiso 1 1 calc R . . C17 C 0.7460(10) 0.1903(6) 0.5441(8) 0.032(3) Uani 1 1 d . . . H17 H 0.7524 0.1616 0.6067 0.038 Uiso 1 1 calc R . . C18 C 0.8543(11) 0.2361(7) 0.5420(9) 0.039(3) Uani 1 1 d . . . C19 C 0.8447(10) 0.2778(6) 0.4499(9) 0.036(3) Uani 1 1 d . . . H19 H 0.9174 0.3103 0.4473 0.043 Uiso 1 1 calc R . . C20 C 0.7271(10) 0.2717(6) 0.3611(9) 0.033(3) Uani 1 1 d . . . H20 H 0.7211 0.2993 0.2976 0.04 Uiso 1 1 calc R . . C21 C 0.9798(12) 0.2434(8) 0.6376(10) 0.057(4) Uani 1 1 d . . . H21A H 0.9643 0.2168 0.6991 0.085 Uiso 1 1 calc R . . H21B H 0.9958 0.2948 0.6565 0.085 Uiso 1 1 calc R . . H21C H 1.061 0.2234 0.6193 0.085 Uiso 1 1 calc R . . P1 P 0.4737(3) 0.21310(16) 0.2517(2) 0.0273(6) Uani 1 1 d . . . Br1 Br 0.41125(10) 0.32043(6) 0.18443(8) 0.0317(3) Uani 1 1 d . . . Br2 Br 0.33490(11) 0.49476(6) 0.11841(9) 0.0413(3) Uani 1 1 d . . . Br3 Br 0.5 0.5 0 0.0363(4) Uani 1 2 d S . . Br4 Br 0.06112(13) 0.41995(8) 0.35800(13) 0.0627(5) Uani 1 1 d . . . Br5 Br 0 0.5 0.5 0.0549(6) Uani 1 2 d S . . 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 0.026(5) 0.030(7) 0.040(6) 0.001(5) 0.010(5) -0.006(5) C2 0.020(5) 0.026(6) 0.053(7) -0.014(6) 0.013(5) -0.010(4) C3 0.031(6) 0.030(7) 0.040(6) -0.011(6) 0.009(5) -0.009(5) C4 0.017(5) 0.038(7) 0.038(6) 0.007(5) 0.006(4) 0.003(5) C5 0.045(7) 0.021(7) 0.052(7) 0.002(6) 0.013(6) -0.011(5) C6 0.036(6) 0.023(6) 0.046(7) -0.004(5) 0.014(5) 0.003(5) C7 0.031(6) 0.043(8) 0.055(8) 0.012(6) 0.016(5) -0.001(5) C8 0.027(5) 0.021(6) 0.025(5) 0.008(4) 0.006(4) -0.004(4) C9 0.022(5) 0.024(6) 0.035(6) -0.003(5) 0.019(4) 0.006(4) C10 0.028(5) 0.019(6) 0.032(6) -0.002(5) 0.003(4) 0.002(4) C11 0.036(6) 0.022(6) 0.032(6) 0.000(5) 0.001(5) 0.005(5) C12 0.036(6) 0.023(6) 0.038(6) -0.008(5) 0.010(5) 0.010(5) C13 0.021(5) 0.026(6) 0.043(6) 0.006(5) 0.007(4) 0.005(4) C14 0.045(7) 0.028(7) 0.036(6) -0.008(5) 0.014(5) -0.004(5) C15 0.030(6) 0.035(7) 0.035(6) -0.009(5) 0.014(4) 0.003(5) C16 0.028(5) 0.023(6) 0.038(6) 0.002(5) 0.012(4) 0.002(4) C17 0.041(6) 0.030(7) 0.025(6) 0.001(5) 0.011(5) 0.003(5) C18 0.033(6) 0.040(8) 0.045(7) -0.012(6) 0.009(5) 0.000(5) C19 0.028(6) 0.035(7) 0.049(7) -0.011(6) 0.018(5) -0.010(5) C20 0.031(6) 0.028(7) 0.041(7) 0.006(5) 0.012(5) 0.002(5) C21 0.044(7) 0.054(10) 0.062(9) -0.008(7) -0.003(6) -0.015(6) P1 0.0275(14) 0.0231(16) 0.0320(15) 0.0022(12) 0.0093(11) 0.0005(11) Br1 0.0355(6) 0.0216(6) 0.0389(6) 0.0017(5) 0.0119(4) 0.0042(5) Br2 0.0432(7) 0.0325(7) 0.0477(7) 0.0023(6) 0.0118(5) 0.0103(5) Br3 0.0369(8) 0.0265(9) 0.0425(9) -0.0041(7) 0.0060(7) 0.0076(7) Br4 0.0405(7) 0.0549(10) 0.0910(11) 0.0235(8) 0.0152(7) -0.0011(6) Br5 0.0267(9) 0.0518(12) 0.0824(13) 0.0301(10) 0.0084(8) -0.0047(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.363(14) . ? C1 C6 1.391(15) . ? C1 P1 1.780(10) . ? C2 C3 1.378(14) . ? C3 C4 1.373(15) . ? C4 C5 1.385(15) . ? C4 C7 1.498(14) . ? C5 C6 1.391(15) . ? C8 C9 1.371(13) . ? C8 C13 1.382(13) . ? C8 P1 1.778(10) . ? C9 C10 1.390(13) . ? C10 C11 1.402(13) . ? C11 C12 1.382(14) . ? C11 C14 1.473(14) . ? C12 C13 1.390(14) . ? C15 C20 1.365(14) . ? C15 C16 1.404(14) . ? C15 P1 1.790(10) . ? C16 C17 1.366(13) . ? C17 C18 1.383(15) . ? C18 C19 1.393(15) . ? C18 C21 1.504(15) . ? C19 C20 1.403(14) . ? P1 Br1 2.179(3) . ? Br2 Br3 2.5423(12) . ? Br3 Br2 2.5423(12) 3_665 ? Br4 Br5 2.5506(17) . ? Br5 Br4 2.5506(17) 3_566 ? 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 C2 C1 C6 120.4(10) . . ? C2 C1 P1 120.0(8) . . ? C6 C1 P1 119.5(8) . . ? C1 C2 C3 119.2(10) . . ? C4 C3 C2 122.4(10) . . ? C3 C4 C5 118.0(10) . . ? C3 C4 C7 122.6(10) . . ? C5 C4 C7 119.4(11) . . ? C4 C5 C6 120.7(11) . . ? C1 C6 C5 119.3(10) . . ? C9 C8 C13 119.9(9) . . ? C9 C8 P1 119.0(7) . . ? C13 C8 P1 121.1(7) . . ? C8 C9 C10 120.7(9) . . ? C9 C10 C11 120.3(9) . . ? C12 C11 C10 117.7(10) . . ? C12 C11 C14 121.8(9) . . ? C10 C11 C14 120.3(9) . . ? C11 C12 C13 121.7(9) . . ? C8 C13 C12 119.4(9) . . ? C20 C15 C16 120.2(10) . . ? C20 C15 P1 121.7(9) . . ? C16 C15 P1 118.0(8) . . ? C17 C16 C15 119.1(10) . . ? C16 C17 C18 121.9(10) . . ? C17 C18 C19 118.9(10) . . ? C17 C18 C21 121.6(11) . . ? C19 C18 C21 119.5(10) . . ? C18 C19 C20 119.7(10) . . ? C15 C20 C19 120.3(10) . . ? C8 P1 C1 112.8(5) . . ? C8 P1 C15 111.0(4) . . ? C1 P1 C15 111.4(5) . . ? C8 P1 Br1 107.5(3) . . ? C1 P1 Br1 107.3(4) . . ? C15 P1 Br1 106.5(4) . . ? Br2 Br3 Br2 180 . 3_665 ? Br4 Br5 Br4 180 . 3_566 ? # END of CIF # Attachment '- Compound10.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-07-08 at 00:49:53 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_rob10 _database_code_depnum_ccdc_archive 'CCDC 865506' #TrackingRef '- Compound10.cif' _audit_creation_date 2010-07-08T00:49:53-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 As1 Br4' _chemical_formula_sum 'C21 H21 As Br4' _chemical_formula_weight 667.73 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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 10.1880(4) _cell_length_b 13.5610(8) _cell_length_c 16.3190(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2254.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1488 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.967 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.6 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.3067 _exptl_absorpt_correction_T_max 0.4251 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.300006E-1 _diffrn_orient_matrix_ub_12 -0.27425E-1 _diffrn_orient_matrix_ub_13 0.537105E-1 _diffrn_orient_matrix_ub_21 -0.852271E-1 _diffrn_orient_matrix_ub_22 0.198253E-1 _diffrn_orient_matrix_ub_23 0.255443E-1 _diffrn_orient_matrix_ub_31 -0.383465E-1 _diffrn_orient_matrix_ub_32 -0.655187E-1 _diffrn_orient_matrix_ub_33 -0.147528E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_av_unetI/netI 0.057 _diffrn_reflns_number 4812 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.48 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.761 _diffrn_measured_fraction_theta_max 0.761 _reflns_number_total 1826 _reflns_number_gt 1606 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0133P)^2^+10.8085P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1826 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.04 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.082 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.58(4) _refine_diff_density_max 0.477 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.125 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.05 2.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.29 2.46 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7116(11) 0.6679(11) 0.1380(6) 0.028(3) Uani 1 1 d . . . C2 C 0.6566(13) 0.7596(11) 0.1187(6) 0.030(3) Uani 1 1 d . . . C3 C 0.7279(13) 0.8233(13) 0.0677(7) 0.038(4) Uani 1 1 d . . . H3 H 0.6919 0.8855 0.0532 0.046 Uiso 1 1 calc R . . C4 C 0.8499(16) 0.7963(13) 0.0385(7) 0.044(4) Uani 1 1 d . . . H4 H 0.8963 0.8401 0.0034 0.053 Uiso 1 1 calc R . . C5 C 0.9056(13) 0.7072(11) 0.0592(7) 0.033(3) Uani 1 1 d . . . H5 H 0.9906 0.6904 0.0397 0.039 Uiso 1 1 calc R . . C6 C 0.8365(11) 0.6418(11) 0.1089(6) 0.026(3) Uani 1 1 d . . . H6 H 0.8737 0.5799 0.1231 0.032 Uiso 1 1 calc R . . C7 C 0.5277(13) 0.7951(13) 0.1533(8) 0.042(4) Uani 1 1 d . . . H7A H 0.4954 0.8506 0.1206 0.063 Uiso 1 1 calc R . . H7B H 0.5405 0.8165 0.2101 0.063 Uiso 1 1 calc R . . H7C H 0.4635 0.7413 0.1518 0.063 Uiso 1 1 calc R . . C8 C 0.5830(11) 0.6408(10) 0.3121(6) 0.025(3) Uani 1 1 d . . . C9 C 0.6705(12) 0.7066(10) 0.3509(6) 0.027(3) Uani 1 1 d . . . C10 C 0.6301(12) 0.7488(11) 0.4227(6) 0.031(3) Uani 1 1 d . . . H10 H 0.6854 0.7954 0.4491 0.037 Uiso 1 1 calc R . . C11 C 0.5090(13) 0.7249(12) 0.4580(7) 0.034(3) Uani 1 1 d . . . H11 H 0.4841 0.7549 0.5082 0.041 Uiso 1 1 calc R . . C12 C 0.4256(12) 0.6587(11) 0.4213(6) 0.032(3) Uani 1 1 d . . . H12 H 0.3447 0.6409 0.4462 0.038 Uiso 1 1 calc R . . C13 C 0.4632(12) 0.6188(11) 0.3471(7) 0.031(3) Uani 1 1 d . . . H13 H 0.4052 0.5752 0.3194 0.037 Uiso 1 1 calc R . . C14 C 0.8075(12) 0.7297(11) 0.3158(7) 0.032(3) Uani 1 1 d . . . H14A H 0.7985 0.7727 0.2679 0.048 Uiso 1 1 calc R . . H14B H 0.8506 0.6681 0.2996 0.048 Uiso 1 1 calc R . . H14C H 0.8605 0.763 0.3576 0.048 Uiso 1 1 calc R . . C15 C 0.7300(10) 0.4633(10) 0.2336(6) 0.024(3) Uani 1 1 d . . . C16 C 0.7637(13) 0.3954(13) 0.1737(8) 0.040(4) Uani 1 1 d . . . C17 C 0.8277(13) 0.3066(14) 0.1996(9) 0.049(4) Uani 1 1 d . . . H17 H 0.8516 0.2581 0.1603 0.059 Uiso 1 1 calc R . . C18 C 0.8552(16) 0.2914(15) 0.2831(10) 0.058(4) Uani 1 1 d . . . H18 H 0.8987 0.2328 0.2998 0.069 Uiso 1 1 calc R . . C19 C 0.8194(14) 0.3612(12) 0.3418(9) 0.039(3) Uani 1 1 d . . . H19 H 0.8371 0.3499 0.3982 0.047 Uiso 1 1 calc R . . C20 C 0.7579(11) 0.4469(11) 0.3168(7) 0.030(3) Uani 1 1 d . . . H20 H 0.7341 0.4952 0.3563 0.036 Uiso 1 1 calc R . . C21 C 0.7350(16) 0.4079(13) 0.0831(7) 0.050(4) Uani 1 1 d . . . H21A H 0.7341 0.4783 0.0694 0.075 Uiso 1 1 calc R . . H21B H 0.6493 0.3789 0.0704 0.075 Uiso 1 1 calc R . . H21C H 0.8032 0.3746 0.051 0.075 Uiso 1 1 calc R . . As1 As 0.63016(11) 0.57875(10) 0.21144(6) 0.0242(3) Uani 1 1 d . . . Br1 Br 0.43659(11) 0.52738(11) 0.15400(6) 0.0337(3) Uani 1 1 d . . . Br2 Br 0.12780(12) 0.48559(11) 0.10615(6) 0.0346(3) Uani 1 1 d . . . Br3 Br 0.10003(11) 0.51676(11) 0.26157(6) 0.0302(3) Uani 1 1 d . . . Br4 Br 0.07017(13) 0.55255(11) 0.41221(7) 0.0390(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 0.023(6) 0.036(10) 0.024(6) 0.008(5) -0.002(5) -0.006(5) C2 0.040(8) 0.022(8) 0.027(6) 0.003(5) -0.002(5) -0.008(6) C3 0.043(8) 0.034(11) 0.038(7) 0.009(6) -0.013(6) -0.008(7) C4 0.057(10) 0.040(11) 0.036(7) -0.005(6) 0.009(6) -0.012(8) C5 0.034(8) 0.025(9) 0.039(7) -0.001(5) 0.009(5) -0.008(6) C6 0.024(7) 0.029(9) 0.027(6) 0.000(5) 0.005(4) -0.008(5) C7 0.044(8) 0.041(11) 0.041(8) -0.002(7) -0.003(6) 0.016(7) C8 0.020(6) 0.024(8) 0.031(6) -0.003(5) -0.004(4) -0.002(5) C9 0.038(7) 0.015(8) 0.026(6) 0.002(5) -0.004(5) 0.001(5) C10 0.022(6) 0.040(10) 0.031(6) 0.000(5) -0.018(5) 0.002(6) C11 0.044(8) 0.034(10) 0.025(6) -0.006(5) 0.001(5) 0.012(7) C12 0.026(6) 0.039(10) 0.031(6) -0.007(5) 0.010(5) 0.006(6) C13 0.030(7) 0.031(10) 0.033(7) -0.003(5) -0.012(5) -0.001(6) C14 0.031(7) 0.030(10) 0.036(7) -0.015(6) -0.002(5) 0.001(6) C15 0.016(5) 0.019(9) 0.038(7) -0.006(5) -0.003(4) -0.003(4) C16 0.026(7) 0.044(13) 0.050(8) -0.014(7) -0.002(5) 0.007(6) C17 0.042(9) 0.032(12) 0.075(10) -0.016(8) -0.001(7) 0.001(7) C18 0.048(9) 0.039(13) 0.087(11) 0.007(8) -0.011(9) 0.002(8) C19 0.051(9) 0.012(10) 0.055(9) -0.001(6) -0.008(6) 0.000(6) C20 0.027(7) 0.019(9) 0.044(7) 0.004(5) 0.007(5) 0.002(5) C21 0.081(12) 0.026(11) 0.044(8) -0.017(7) 0.004(7) 0.000(8) As1 0.0228(6) 0.0231(8) 0.0268(6) -0.0032(5) 0.0016(5) -0.0012(5) Br1 0.0282(6) 0.0409(10) 0.0320(6) -0.0048(5) -0.0026(5) -0.0062(6) Br2 0.0314(6) 0.0367(9) 0.0357(6) -0.0026(5) -0.0003(5) 0.0012(6) Br3 0.0291(6) 0.0249(8) 0.0365(6) -0.0005(5) 0.0006(4) -0.0008(5) Br4 0.0474(8) 0.0340(9) 0.0355(7) -0.0022(5) 0.0003(5) -0.0008(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.40(2) . ? C1 C6 1.403(17) . ? C1 As1 1.894(12) . ? C2 C3 1.402(18) . ? C2 C7 1.508(18) . ? C3 C4 1.38(2) . ? C3 H3 0.95 . ? C4 C5 1.38(2) . ? C4 H4 0.95 . ? C5 C6 1.393(17) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C13 1.381(17) . ? C8 C9 1.411(17) . ? C8 As1 1.907(11) . ? C9 C10 1.366(17) . ? C9 C14 1.541(17) . ? C10 C11 1.400(18) . ? C10 H10 0.95 . ? C11 C12 1.37(2) . ? C11 H11 0.95 . ? C12 C13 1.380(16) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 C16 1.387(18) . ? C15 C20 1.405(15) . ? C15 As1 1.902(13) . ? C16 C17 1.43(2) . ? C16 C21 1.516(18) . ? C17 C18 1.41(2) . ? C17 H17 0.95 . ? C18 C19 1.39(2) . ? C18 H18 0.95 . ? C19 C20 1.38(2) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? As1 Br1 2.2919(17) . ? Br2 Br3 2.5867(15) . ? Br3 Br4 2.5240(16) . ? 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 C2 C1 C6 120.7(12) . . ? C2 C1 As1 122.3(10) . . ? C6 C1 As1 116.8(11) . . ? C1 C2 C3 118.3(13) . . ? C1 C2 C7 123.2(12) . . ? C3 C2 C7 118.5(15) . . ? C4 C3 C2 120.6(16) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 121.2(14) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.5(13) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 119.7(14) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 120.7(11) . . ? C13 C8 As1 118.9(9) . . ? C9 C8 As1 120.4(9) . . ? C10 C9 C8 117.3(11) . . ? C10 C9 C14 120.4(11) . . ? C8 C9 C14 122.2(10) . . ? C9 C10 C11 121.4(12) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 C10 121.1(11) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 117.8(12) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 121.1 . . ? C8 C13 C12 121.5(11) . . ? C8 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 121.8(12) . . ? C16 C15 As1 123.0(9) . . ? C20 C15 As1 115.0(8) . . ? C15 C16 C17 117.5(12) . . ? C15 C16 C21 124.5(14) . . ? C17 C16 C21 118.0(13) . . ? C18 C17 C16 120.0(14) . . ? C18 C17 H17 120 . . ? C16 C17 H17 120 . . ? C19 C18 C17 120.9(16) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C20 C19 C18 119.1(13) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C19 C20 C15 120.7(12) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 As1 C15 114.3(5) . . ? C1 As1 C8 112.0(6) . . ? C15 As1 C8 109.5(5) . . ? C1 As1 Br1 108.2(3) . . ? C15 As1 Br1 106.7(3) . . ? C8 As1 Br1 105.7(3) . . ? Br4 Br3 Br2 178.19(8) . . ? # END of CIF # Attachment '- Compound11.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-02-28 at 00:07:48 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_rob11 _database_code_depnum_ccdc_archive 'CCDC 865507' #TrackingRef '- Compound11.cif' _audit_creation_date 2011-02-28T00:07:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 As1 Br4' _chemical_formula_sum 'C21 H21 As Br4' _chemical_formula_weight 667.94 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.2560(2) _cell_length_b 11.3603(2) _cell_length_c 18.7646(6) _cell_angle_alpha 90 _cell_angle_beta 106.8340(10) _cell_angle_gamma 90 _cell_volume 2296.64(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5041 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.443 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.2654 _exptl_absorpt_correction_T_max 0.7141 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.494859E-1 _diffrn_orient_matrix_ub_12 -0.735343E-1 _diffrn_orient_matrix_ub_13 -0.157283E-1 _diffrn_orient_matrix_ub_21 -0.73991E-1 _diffrn_orient_matrix_ub_22 0.38999E-1 _diffrn_orient_matrix_ub_23 0.90068E-2 _diffrn_orient_matrix_ub_31 -0.263022E-1 _diffrn_orient_matrix_ub_32 0.286415E-1 _diffrn_orient_matrix_ub_33 -0.52645E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.091 _diffrn_reflns_av_unetI/netI 0.0724 _diffrn_reflns_number 19739 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 26.5 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 4974 _reflns_number_gt 3874 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0731P)^2^+4.5428P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4974 _refine_ls_number_parameters 476 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.53(6) _refine_diff_density_max 0.959 _refine_diff_density_min -1.031 _refine_diff_density_rms 0.189 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.0499 2.0058 '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' 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 0.8965(13) 0.4173(11) 0.4389(7) 0.027(3) Uani 1 1 d . . . C2 C 0.8091(14) 0.4545(13) 0.4729(8) 0.030(3) Uani 1 1 d . . . H2 H 0.8166 0.434 0.522 0.037 Uiso 1 1 calc R . . C3 C 0.7121(12) 0.5216(12) 0.4337(7) 0.027(3) Uani 1 1 d . . . H3 H 0.6549 0.5495 0.4567 0.032 Uiso 1 1 calc R . . C4 C 0.6977(13) 0.5488(11) 0.3595(7) 0.027(3) Uani 1 1 d . . . C5 C 0.7809(12) 0.5078(10) 0.3256(7) 0.022(3) Uani 1 1 d . . . H5 H 0.7705 0.5253 0.2758 0.027 Uiso 1 1 calc R . . C6 C 0.8827(13) 0.4391(11) 0.3652(8) 0.028(3) Uani 1 1 d . . . H6 H 0.939 0.4095 0.342 0.033 Uiso 1 1 calc R . . C7 C 0.5900(13) 0.6271(13) 0.3169(9) 0.035(3) Uani 1 1 d . . . H7A H 0.6048 0.7065 0.3347 0.052 Uiso 1 1 calc R . . H7B H 0.5142 0.599 0.3245 0.052 Uiso 1 1 calc R . . H7C H 0.5834 0.6249 0.2647 0.052 Uiso 1 1 calc R . . C8 C 1.1694(12) 0.4486(12) 0.5534(7) 0.026(3) Uani 1 1 d . . . C9 C 1.1908(12) 0.4525(12) 0.6308(7) 0.023(3) Uani 1 1 d . . . H9 H 1.1514 0.4006 0.6549 0.027 Uiso 1 1 calc R . . C10 C 1.2742(12) 0.5381(12) 0.6705(7) 0.025(3) Uani 1 1 d . . . H10 H 1.2923 0.5419 0.722 0.03 Uiso 1 1 calc R . . C11 C 1.3292(12) 0.6162(12) 0.6340(7) 0.026(3) Uani 1 1 d . . . C12 C 1.3080(12) 0.6050(14) 0.5577(8) 0.031(3) Uani 1 1 d . . . H12 H 1.3512 0.6538 0.534 0.038 Uiso 1 1 calc R . . C13 C 1.2260(13) 0.5250(13) 0.5157(8) 0.030(3) Uani 1 1 d . . . H13 H 1.209 0.522 0.4642 0.036 Uiso 1 1 calc R . . C14 C 1.4146(13) 0.7079(12) 0.6770(7) 0.027(3) Uani 1 1 d . . . H14A H 1.3684 0.7632 0.6971 0.041 Uiso 1 1 calc R . . H14B H 1.4535 0.7482 0.6448 0.041 Uiso 1 1 calc R . . H14C H 1.477 0.6714 0.7169 0.041 Uiso 1 1 calc R . . C15 C 1.1131(13) 0.2477(11) 0.4309(7) 0.024(3) Uani 1 1 d . . . C16 C 1.0299(13) 0.1829(12) 0.3753(8) 0.032(3) Uani 1 1 d . . . H16 H 0.9452 0.1868 0.3699 0.038 Uiso 1 1 calc R . . C17 C 1.0737(13) 0.1130(13) 0.3285(7) 0.028(3) Uani 1 1 d . . . H17 H 1.0184 0.0682 0.2922 0.034 Uiso 1 1 calc R . . C18 C 1.2028(13) 0.1087(12) 0.3351(7) 0.029(3) Uani 1 1 d . . . C19 C 1.2835(13) 0.1759(12) 0.3920(8) 0.028(3) Uani 1 1 d . . . H19 H 1.3683 0.1751 0.3975 0.034 Uiso 1 1 calc R . . C20 C 1.2383(11) 0.2431(13) 0.4400(7) 0.026(3) Uani 1 1 d . . . H20 H 1.2928 0.285 0.4783 0.031 Uiso 1 1 calc R . . C21 C 1.2523(16) 0.0349(15) 0.2849(9) 0.045(4) Uani 1 1 d . . . H21A H 1.2513 0.0792 0.2412 0.068 Uiso 1 1 calc R . . H21B H 1.2016 -0.034 0.2709 0.068 Uiso 1 1 calc R . . H21C H 1.3359 0.0119 0.3103 0.068 Uiso 1 1 calc R . . C22 C 0.8356(15) 0.2050(13) 0.9436(8) 0.033(3) Uani 1 1 d . . . C23 C 0.7791(13) 0.2824(11) 0.9819(7) 0.026(3) Uani 1 1 d . . . H23 H 0.804 0.2855 1.0337 0.031 Uiso 1 1 calc R . . C24 C 0.6841(13) 0.3546(12) 0.9401(7) 0.028(3) Uani 1 1 d . . . H24 H 0.6489 0.4097 0.9646 0.034 Uiso 1 1 calc R . . C25 C 0.6395(12) 0.3466(12) 0.8617(7) 0.025(3) Uani 1 1 d . . . C26 C 0.6948(14) 0.2637(13) 0.8266(7) 0.031(3) Uani 1 1 d . . . H26 H 0.6649 0.2556 0.7752 0.037 Uiso 1 1 calc R . . C27 C 0.7936(13) 0.1919(12) 0.8658(7) 0.028(3) Uani 1 1 d . . . H27 H 0.8299 0.1379 0.8412 0.034 Uiso 1 1 calc R . . C28 C 0.5336(14) 0.4218(15) 0.8200(9) 0.040(4) Uani 1 1 d . . . H28A H 0.5439 0.4424 0.7725 0.059 Uiso 1 1 calc R . . H28B H 0.5313 0.4922 0.8479 0.059 Uiso 1 1 calc R . . H28C H 0.4573 0.3793 0.8126 0.059 Uiso 1 1 calc R . . C29 C 1.1033(14) 0.2014(11) 1.0675(7) 0.029(3) Uani 1 1 d . . . C30 C 1.0840(12) 0.2437(11) 1.1318(8) 0.028(3) Uani 1 1 d . . . H30 H 1.0107 0.2266 1.143 0.034 Uiso 1 1 calc R . . C31 C 1.1725(14) 0.3107(13) 1.1788(9) 0.035(3) Uani 1 1 d . . . H31 H 1.16 0.337 1.223 0.042 Uiso 1 1 calc R . . C32 C 1.2827(14) 0.3411(12) 1.1622(9) 0.036(4) Uani 1 1 d . . . C33 C 1.3001(15) 0.2939(14) 1.0971(9) 0.039(4) Uani 1 1 d . . . H33 H 1.3732 0.3103 1.0853 0.047 Uiso 1 1 calc R . . C34 C 1.2123(14) 0.2242(15) 1.0502(8) 0.039(3) Uani 1 1 d . . . H34 H 1.2258 0.1928 1.0074 0.047 Uiso 1 1 calc R . . C35 C 1.3766(14) 0.4200(13) 1.2120(9) 0.040(4) Uani 1 1 d . . . H35A H 1.458 0.3878 1.219 0.06 Uiso 1 1 calc R . . H35B H 1.3602 0.4263 1.2593 0.06 Uiso 1 1 calc R . . H35C H 1.372 0.4966 1.1897 0.06 Uiso 1 1 calc R . . C36 C 0.9151(12) -0.0011(10) 1.0591(8) 0.026(3) Uani 1 1 d . . . C37 C 1.0055(12) -0.0649(11) 1.1124(8) 0.026(3) Uani 1 1 d . . . H37 H 1.0894 -0.054 1.1174 0.032 Uiso 1 1 calc R . . C38 C 0.9670(14) -0.1452(13) 1.1579(8) 0.032(3) Uani 1 1 d . . . H38 H 1.0251 -0.1879 1.1939 0.038 Uiso 1 1 calc R . . C39 C 0.8407(13) -0.1602(12) 1.1484(8) 0.028(3) Uani 1 1 d . . . C40 C 0.7555(12) -0.0971(10) 1.0951(7) 0.022(3) Uani 1 1 d . . . H40 H 0.6714 -0.1086 1.0892 0.026 Uiso 1 1 calc R . . C41 C 0.7912(13) -0.0167(12) 1.0497(8) 0.030(3) Uani 1 1 d . . . H41 H 0.7323 0.0255 1.0138 0.036 Uiso 1 1 calc R . . C42 C 0.7961(13) -0.2472(14) 1.1960(8) 0.034(3) Uani 1 1 d . . . H42A H 0.7364 -0.2099 1.2162 0.051 Uiso 1 1 calc R . . H42B H 0.8654 -0.2737 1.236 0.051 Uiso 1 1 calc R . . H42C H 0.7583 -0.3134 1.1662 0.051 Uiso 1 1 calc R . . As1 As 1.04706(12) 0.34143(11) 0.49523(7) 0.0230(3) Uani 1 1 d . . . As2 As 0.97216(13) 0.11326(11) 1.00079(8) 0.0250(3) Uani 1 1 d . . . Br1 Br 0.99450(13) 0.22419(12) 0.57941(7) 0.0294(3) Uani 1 1 d . . . Br2 Br 0.53636(15) 0.36515(15) 0.55758(9) 0.0421(4) Uani 1 1 d . . . Br3 Br 0.69975(13) 0.22517(13) 0.62652(8) 0.0311(3) Uani 1 1 d . . . Br4 Br 0.87188(14) 0.07933(12) 0.69799(8) 0.0343(3) Uani 1 1 d . . . Br5 Br 1.05713(15) 0.02683(12) 0.91812(8) 0.0350(3) Uani 1 1 d . . . Br6 Br 1.21045(16) -0.24732(15) 0.81061(9) 0.0447(4) Uani 1 1 d . . . Br7 Br 1.34443(14) -0.07467(13) 0.87760(8) 0.0333(3) Uani 1 1 d . . . Br8 Br 1.47121(15) 0.09604(15) 0.94649(10) 0.0474(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.030(8) 0.020(6) 0.031(7) -0.010(5) 0.009(6) -0.003(5) C2 0.034(8) 0.043(8) 0.018(7) 0.005(6) 0.014(6) 0.016(6) C3 0.026(7) 0.028(7) 0.034(8) 0.007(6) 0.021(6) -0.005(6) C4 0.030(8) 0.022(7) 0.025(7) -0.002(5) 0.003(6) -0.005(5) C5 0.023(7) 0.011(6) 0.033(7) -0.007(5) 0.008(6) 0.000(5) C6 0.032(8) 0.013(6) 0.043(8) -0.004(5) 0.019(7) 0.007(5) C7 0.020(7) 0.030(7) 0.050(9) -0.003(6) 0.005(7) 0.009(6) C8 0.020(7) 0.030(7) 0.026(7) 0.007(5) 0.005(6) 0.006(5) C9 0.021(7) 0.029(7) 0.018(7) 0.002(5) 0.004(5) -0.010(5) C10 0.026(7) 0.024(6) 0.026(7) 0.007(5) 0.008(6) 0.006(5) C11 0.021(7) 0.021(6) 0.030(7) -0.001(5) -0.001(6) 0.006(5) C12 0.017(7) 0.042(8) 0.031(8) -0.002(6) 0.002(6) 0.004(6) C13 0.029(8) 0.030(7) 0.028(7) 0.006(6) 0.003(6) -0.007(6) C14 0.027(7) 0.024(6) 0.028(7) -0.003(5) 0.002(6) -0.001(5) C15 0.032(8) 0.017(6) 0.017(6) 0.003(5) -0.003(5) 0.004(5) C16 0.024(8) 0.031(7) 0.034(8) -0.001(6) -0.001(6) 0.004(6) C17 0.026(7) 0.035(7) 0.023(7) -0.004(6) 0.006(6) -0.005(6) C18 0.028(8) 0.028(7) 0.025(7) -0.001(6) 0.002(6) -0.003(6) C19 0.022(7) 0.032(7) 0.031(7) -0.003(6) 0.009(6) -0.003(6) C20 0.007(6) 0.040(7) 0.029(7) 0.006(6) 0.003(5) 0.000(5) C21 0.061(11) 0.040(8) 0.038(9) -0.006(7) 0.021(8) 0.008(8) C22 0.046(9) 0.031(7) 0.030(8) 0.010(6) 0.022(7) -0.004(6) C23 0.038(8) 0.024(6) 0.012(6) -0.002(5) 0.003(6) 0.007(6) C24 0.034(8) 0.021(6) 0.031(7) 0.005(5) 0.011(6) 0.006(5) C25 0.024(7) 0.031(7) 0.017(6) 0.010(5) 0.002(5) 0.001(6) C26 0.034(8) 0.038(8) 0.011(6) -0.002(5) -0.009(6) -0.007(6) C27 0.023(7) 0.034(7) 0.027(7) 0.001(6) 0.007(6) 0.004(6) C28 0.035(9) 0.039(8) 0.039(9) 0.002(7) 0.002(7) 0.011(7) C29 0.041(9) 0.024(7) 0.025(7) 0.006(5) 0.011(6) -0.003(6) C30 0.019(7) 0.017(6) 0.052(9) -0.005(6) 0.017(6) -0.003(5) C31 0.038(9) 0.028(7) 0.040(9) -0.010(6) 0.012(7) 0.007(6) C32 0.036(8) 0.011(6) 0.055(10) 0.001(6) 0.001(7) 0.000(6) C33 0.034(9) 0.040(8) 0.049(10) 0.004(7) 0.021(8) -0.002(7) C34 0.040(9) 0.042(8) 0.032(8) -0.008(7) 0.008(7) -0.015(7) C35 0.030(9) 0.028(7) 0.058(10) 0.009(7) 0.007(8) 0.002(6) C36 0.021(7) 0.010(6) 0.046(8) 0.006(5) 0.008(6) -0.005(5) C37 0.014(6) 0.018(6) 0.042(8) -0.010(6) 0.000(6) 0.004(5) C38 0.035(8) 0.030(7) 0.029(8) 0.003(6) 0.005(6) 0.006(6) C39 0.028(8) 0.027(6) 0.032(8) -0.005(6) 0.011(6) 0.012(6) C40 0.025(7) 0.018(6) 0.028(7) 0.002(5) 0.016(6) -0.013(5) C41 0.028(8) 0.023(6) 0.039(8) 0.008(6) 0.012(7) -0.002(5) C42 0.024(8) 0.045(8) 0.036(8) 0.000(6) 0.016(6) -0.005(6) As1 0.0226(7) 0.0195(6) 0.0273(7) 0.0013(5) 0.0078(6) -0.0005(5) As2 0.0281(8) 0.0195(6) 0.0283(7) 0.0003(5) 0.0097(6) 0.0001(5) Br1 0.0295(7) 0.0253(6) 0.0337(7) 0.0060(5) 0.0097(6) -0.0036(5) Br2 0.0277(8) 0.0495(9) 0.0446(9) 0.0002(7) 0.0035(7) 0.0006(7) Br3 0.0288(7) 0.0375(7) 0.0297(7) -0.0050(6) 0.0130(6) -0.0033(6) Br4 0.0393(8) 0.0361(7) 0.0308(8) 0.0012(6) 0.0154(6) 0.0010(6) Br5 0.0448(9) 0.0269(6) 0.0381(8) -0.0017(6) 0.0195(7) 0.0062(6) Br6 0.0484(10) 0.0543(10) 0.0372(9) -0.0054(7) 0.0214(8) -0.0104(7) Br7 0.0274(8) 0.0425(8) 0.0316(8) 0.0067(6) 0.0111(6) 0.0030(6) Br8 0.0329(9) 0.0461(9) 0.0569(10) 0.0045(8) 0.0031(8) -0.0035(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C6 1.369(19) . ? C1 C2 1.384(18) . ? C1 As1 1.922(14) . ? C2 C3 1.359(19) . ? C3 C4 1.389(19) . ? C4 C5 1.356(18) . ? C4 C7 1.529(19) . ? C5 C6 1.408(18) . ? C8 C13 1.386(18) . ? C8 C9 1.401(18) . ? C8 As1 1.923(14) . ? C9 C10 1.406(18) . ? C10 C11 1.372(19) . ? C11 C12 1.388(19) . ? C11 C14 1.487(18) . ? C12 C13 1.371(19) . ? C15 C20 1.371(18) . ? C15 C16 1.394(18) . ? C15 As1 1.914(13) . ? C16 C17 1.376(19) . ? C17 C18 1.424(19) . ? C18 C19 1.410(19) . ? C18 C21 1.484(19) . ? C19 C20 1.384(19) . ? C22 C23 1.400(19) . ? C22 C27 1.407(19) . ? C22 As2 1.909(15) . ? C23 C24 1.395(18) . ? C24 C25 1.412(18) . ? C25 C26 1.40(2) . ? C25 C28 1.491(19) . ? C26 C27 1.403(19) . ? C29 C30 1.374(19) . ? C29 C34 1.38(2) . ? C29 As2 1.918(14) . ? C30 C31 1.36(2) . ? C31 C32 1.41(2) . ? C32 C33 1.40(2) . ? C32 C35 1.49(2) . ? C33 C34 1.37(2) . ? C36 C41 1.366(19) . ? C36 C37 1.404(18) . ? C36 As2 1.924(12) . ? C37 C38 1.40(2) . ? C38 C39 1.39(2) . ? C39 C40 1.370(19) . ? C39 C42 1.513(19) . ? C40 C41 1.385(17) . ? As1 Br1 2.2716(18) . ? As2 Br5 2.2682(19) . ? Br2 Br3 2.491(2) . ? Br3 Br4 2.606(2) . ? Br6 Br7 2.570(2) . ? Br7 Br8 2.530(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 C6 C1 C2 121.5(13) . . ? C6 C1 As1 117.4(10) . . ? C2 C1 As1 121.0(10) . . ? C3 C2 C1 119.2(12) . . ? C2 C3 C4 120.7(12) . . ? C5 C4 C3 119.8(13) . . ? C5 C4 C7 120.3(13) . . ? C3 C4 C7 119.9(13) . . ? C4 C5 C6 120.7(13) . . ? C1 C6 C5 118.1(12) . . ? C13 C8 C9 122.8(13) . . ? C13 C8 As1 117.7(10) . . ? C9 C8 As1 119.2(9) . . ? C8 C9 C10 117.3(11) . . ? C11 C10 C9 120.7(12) . . ? C10 C11 C12 119.2(13) . . ? C10 C11 C14 119.7(12) . . ? C12 C11 C14 121.0(12) . . ? C13 C12 C11 122.6(13) . . ? C12 C13 C8 117.1(13) . . ? C20 C15 C16 121.1(12) . . ? C20 C15 As1 121.1(10) . . ? C16 C15 As1 117.8(11) . . ? C17 C16 C15 119.7(13) . . ? C16 C17 C18 120.6(13) . . ? C19 C18 C17 117.7(12) . . ? C19 C18 C21 120.6(13) . . ? C17 C18 C21 121.7(12) . . ? C20 C19 C18 120.9(12) . . ? C15 C20 C19 119.9(12) . . ? C23 C22 C27 122.2(13) . . ? C23 C22 As2 117.8(10) . . ? C27 C22 As2 120.0(10) . . ? C24 C23 C22 118.0(12) . . ? C23 C24 C25 122.1(12) . . ? C26 C25 C24 117.5(12) . . ? C26 C25 C28 122.5(12) . . ? C24 C25 C28 119.9(12) . . ? C25 C26 C27 122.6(12) . . ? C26 C27 C22 117.4(12) . . ? C30 C29 C34 121.2(13) . . ? C30 C29 As2 117.9(10) . . ? C34 C29 As2 120.9(10) . . ? C31 C30 C29 119.7(13) . . ? C30 C31 C32 121.5(13) . . ? C33 C32 C31 117.0(13) . . ? C33 C32 C35 121.6(14) . . ? C31 C32 C35 121.3(14) . . ? C34 C33 C32 121.7(15) . . ? C33 C34 C29 118.9(14) . . ? C41 C36 C37 121.8(12) . . ? C41 C36 As2 120.7(10) . . ? C37 C36 As2 117.5(10) . . ? C38 C37 C36 118.9(12) . . ? C39 C38 C37 119.1(13) . . ? C40 C39 C38 120.2(13) . . ? C40 C39 C42 119.5(12) . . ? C38 C39 C42 120.4(12) . . ? C39 C40 C41 121.8(13) . . ? C36 C41 C40 118.3(13) . . ? C15 As1 C1 110.2(5) . . ? C15 As1 C8 111.4(6) . . ? C1 As1 C8 113.6(6) . . ? C15 As1 Br1 109.8(4) . . ? C1 As1 Br1 106.2(4) . . ? C8 As1 Br1 105.3(4) . . ? C22 As2 C29 115.1(6) . . ? C22 As2 C36 109.9(6) . . ? C29 As2 C36 107.6(6) . . ? C22 As2 Br5 106.4(4) . . ? C29 As2 Br5 105.9(4) . . ? C36 As2 Br5 111.9(4) . . ? Br2 Br3 Br4 179.52(8) . . ? Br8 Br7 Br6 177.94(8) . . ? # END of CIF # Attachment '- Compound12.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-03-03 at 12:18:33 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_rob12 _database_code_depnum_ccdc_archive 'CCDC 865508' #TrackingRef '- Compound12.cif' _audit_creation_date 2011-03-03T12:18:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H15 As1 Br4' _chemical_formula_sum 'C18 H15 As Br4' _chemical_formula_weight 625.7 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.0850(2) _cell_length_b 10.8700(2) _cell_length_c 20.3397(5) _cell_angle_alpha 90 _cell_angle_beta 118.0210(10) _cell_angle_gamma 90 _cell_volume 1968.34(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8038 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 2.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 9.843 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.745392E-1 _diffrn_orient_matrix_ub_12 0.103657E-1 _diffrn_orient_matrix_ub_13 0.34855E-1 _diffrn_orient_matrix_ub_21 0.637474E-1 _diffrn_orient_matrix_ub_22 -0.87962E-2 _diffrn_orient_matrix_ub_23 0.43442E-1 _diffrn_orient_matrix_ub_31 0.14863E-1 _diffrn_orient_matrix_ub_32 0.909961E-1 _diffrn_orient_matrix_ub_33 -0.5768E-3 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0915 _diffrn_reflns_av_unetI/netI 0.0648 _diffrn_reflns_number 14127 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3868 _reflns_number_gt 2753 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _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^)+(0.0917P)^2^+3.7795P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3868 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.081 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.153 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.397 _refine_diff_density_min -1.106 _refine_diff_density_rms 0.218 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.05 2.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.29 2.46 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.36305(9) 0.47368(7) 0.26207(5) 0.0269(2) Uani 1 1 d . . . As1 As 0.59183(8) 0.39126(7) 0.29428(4) 0.0211(2) Uani 1 1 d . . . C1 C 0.6250(8) 0.2629(7) 0.3649(4) 0.0237(17) Uani 1 1 d . . . C2 C 0.5153(9) 0.2283(7) 0.3836(5) 0.0284(18) Uani 1 1 d . . . H2 H 0.4225 0.2713 0.3641 0.034 Uiso 1 1 calc R . . C3 C 0.5428(10) 0.1295(8) 0.4315(5) 0.036(2) Uani 1 1 d . . . H3 H 0.4681 0.1044 0.4447 0.043 Uiso 1 1 calc R . . C4 C 0.6773(10) 0.0676(7) 0.4601(5) 0.0288(18) Uani 1 1 d . . . H4 H 0.6952 0.0001 0.4929 0.035 Uiso 1 1 calc R . . C5 C 0.7876(9) 0.1035(8) 0.4409(5) 0.032(2) Uani 1 1 d . . . H5 H 0.8806 0.0607 0.461 0.038 Uiso 1 1 calc R . . C6 C 0.7623(9) 0.2009(8) 0.3930(5) 0.0309(19) Uani 1 1 d . . . H6 H 0.8365 0.2253 0.3794 0.037 Uiso 1 1 calc R . . C7 C 0.5861(8) 0.3252(7) 0.2061(4) 0.0220(16) Uani 1 1 d . . . C8 C 0.4502(9) 0.2961(7) 0.1446(4) 0.0241(17) Uani 1 1 d . . . H8 H 0.3583 0.3148 0.1448 0.029 Uiso 1 1 calc R . . C9 C 0.4489(9) 0.2409(7) 0.0843(5) 0.0276(18) Uani 1 1 d . . . H9 H 0.3562 0.2219 0.0419 0.033 Uiso 1 1 calc R . . C10 C 0.5842(9) 0.2125(7) 0.0852(5) 0.0281(18) Uani 1 1 d . . . H10 H 0.5837 0.1734 0.0433 0.034 Uiso 1 1 calc R . . C11 C 0.7202(9) 0.2409(7) 0.1469(5) 0.0259(17) Uani 1 1 d . . . H11 H 0.8119 0.2198 0.1472 0.031 Uiso 1 1 calc R . . C12 C 0.7228(9) 0.2991(7) 0.2074(5) 0.0256(17) Uani 1 1 d . . . H12 H 0.8153 0.3211 0.249 0.031 Uiso 1 1 calc R . . C13 C 0.7418(8) 0.5164(7) 0.3362(4) 0.0197(15) Uani 1 1 d . . . C14 C 0.8058(9) 0.5386(7) 0.4117(4) 0.0246(17) Uani 1 1 d . . . H14 H 0.7813 0.4888 0.4428 0.029 Uiso 1 1 calc R . . C15 C 0.9061(9) 0.6347(7) 0.4412(5) 0.0298(19) Uani 1 1 d . . . H15 H 0.9502 0.652 0.4929 0.036 Uiso 1 1 calc R . . C16 C 0.9429(9) 0.7061(7) 0.3954(5) 0.0274(18) Uani 1 1 d . . . H16 H 1.0133 0.7713 0.4164 0.033 Uiso 1 1 calc R . . C17 C 0.8774(8) 0.6831(7) 0.3185(5) 0.0262(17) Uani 1 1 d . . . H17 H 0.9015 0.7327 0.2871 0.031 Uiso 1 1 calc R . . C18 C 0.7780(9) 0.5876(7) 0.2898(5) 0.0279(18) Uani 1 1 d . . . H18 H 0.7335 0.5697 0.2381 0.034 Uiso 1 1 calc R . . Br2 Br -0.01886(10) 0.50894(8) 0.16769(5) 0.0359(3) Uani 1 1 d . . . Br3 Br -0.12210(8) 0.72684(7) 0.12716(4) 0.0252(2) Uani 1 1 d . . . Br4 Br -0.21782(10) 0.94306(8) 0.09046(5) 0.0344(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 Br1 0.0235(4) 0.0266(4) 0.0313(5) 0.0003(3) 0.0134(4) 0.0040(3) As1 0.0200(4) 0.0226(4) 0.0207(4) -0.0001(3) 0.0097(3) 0.0005(3) C1 0.023(4) 0.024(4) 0.020(4) -0.005(3) 0.006(3) -0.001(3) C2 0.025(4) 0.031(4) 0.033(5) -0.002(4) 0.017(4) 0.001(3) C3 0.041(5) 0.036(5) 0.031(5) 0.008(4) 0.016(4) 0.001(4) C4 0.042(5) 0.025(4) 0.020(4) 0.000(3) 0.016(4) -0.005(4) C5 0.029(4) 0.027(4) 0.032(5) 0.009(4) 0.009(4) 0.008(4) C6 0.023(4) 0.036(5) 0.035(5) 0.001(4) 0.014(4) -0.004(4) C7 0.031(4) 0.019(4) 0.024(4) -0.001(3) 0.019(4) -0.009(3) C8 0.024(4) 0.022(4) 0.027(4) 0.001(3) 0.012(3) -0.005(3) C9 0.027(4) 0.027(4) 0.029(5) -0.001(4) 0.013(4) -0.002(4) C10 0.036(5) 0.021(4) 0.027(5) 0.006(3) 0.015(4) 0.005(4) C11 0.027(4) 0.025(4) 0.027(4) -0.005(4) 0.015(4) -0.001(3) C12 0.026(4) 0.020(4) 0.032(5) 0.001(3) 0.015(4) 0.002(3) C13 0.014(4) 0.021(4) 0.021(4) 0.002(3) 0.006(3) 0.001(3) C14 0.029(4) 0.025(4) 0.020(4) -0.001(3) 0.012(4) 0.003(3) C15 0.034(5) 0.026(4) 0.031(5) -0.007(4) 0.017(4) 0.003(4) C16 0.032(4) 0.019(4) 0.034(5) -0.009(3) 0.018(4) -0.006(3) C17 0.026(4) 0.021(4) 0.030(5) 0.002(3) 0.012(4) -0.003(3) C18 0.024(4) 0.031(4) 0.028(5) 0.008(4) 0.012(4) 0.000(4) Br2 0.0299(5) 0.0320(5) 0.0441(6) 0.0032(4) 0.0160(4) 0.0059(4) Br3 0.0214(4) 0.0303(4) 0.0249(4) -0.0026(3) 0.0117(3) -0.0017(3) Br4 0.0474(5) 0.0275(5) 0.0337(5) -0.0015(4) 0.0235(4) 0.0006(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Br1 As1 2.2660(10) . ? As1 C7 1.907(7) . ? As1 C13 1.912(7) . ? As1 C1 1.916(8) . ? C1 C2 1.381(11) . ? C1 C6 1.399(11) . ? C2 C3 1.388(12) . ? C2 H2 0.95 . ? C3 C4 1.375(12) . ? C3 H3 0.95 . ? C4 C5 1.396(11) . ? C4 H4 0.95 . ? C5 C6 1.379(11) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.389(11) . ? C7 C12 1.395(11) . ? C8 C9 1.360(11) . ? C8 H8 0.95 . ? C9 C10 1.391(11) . ? C9 H9 0.95 . ? C10 C11 1.391(12) . ? C10 H10 0.95 . ? C11 C12 1.373(11) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 C14 1.378(11) . ? C13 C18 1.396(11) . ? C14 C15 1.379(11) . ? C14 H14 0.95 . ? C15 C16 1.390(12) . ? C15 H15 0.95 . ? C16 C17 1.406(11) . ? C16 H16 0.95 . ? C17 C18 1.368(11) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? Br2 Br3 2.5626(11) . ? Br3 Br4 2.5171(11) . ? 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 C7 As1 C13 110.8(3) . . ? C7 As1 C1 110.4(3) . . ? C13 As1 C1 111.2(3) . . ? C7 As1 Br1 107.5(2) . . ? C13 As1 Br1 109.4(2) . . ? C1 As1 Br1 107.5(2) . . ? C2 C1 C6 121.6(7) . . ? C2 C1 As1 121.7(6) . . ? C6 C1 As1 116.6(6) . . ? C3 C2 C1 118.9(8) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C4 C3 C2 120.5(8) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.2(8) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.3(8) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 118.5(7) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C8 C7 C12 121.2(7) . . ? C8 C7 As1 120.9(5) . . ? C12 C7 As1 117.8(6) . . ? C9 C8 C7 120.0(7) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 119.5(8) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 120.5(8) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 120.4(7) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C7 118.3(8) . . ? C11 C12 H12 120.8 . . ? C7 C12 H12 120.8 . . ? C14 C13 C18 121.4(7) . . ? C14 C13 As1 118.7(6) . . ? C18 C13 As1 119.8(6) . . ? C13 C14 C15 118.7(7) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C14 C15 C16 120.3(8) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 120.8(7) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C18 C17 C16 118.4(7) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C17 C18 C13 120.3(8) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? Br4 Br3 Br2 178.48(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 C7 As1 C1 C2 -112.0(7) . . . . ? C13 As1 C1 C2 124.5(7) . . . . ? Br1 As1 C1 C2 4.9(7) . . . . ? C7 As1 C1 C6 64.1(7) . . . . ? C13 As1 C1 C6 -59.4(7) . . . . ? Br1 As1 C1 C6 -179.0(5) . . . . ? C6 C1 C2 C3 0.0(12) . . . . ? As1 C1 C2 C3 175.9(6) . . . . ? C1 C2 C3 C4 0.3(13) . . . . ? C2 C3 C4 C5 -0.1(13) . . . . ? C3 C4 C5 C6 -0.3(13) . . . . ? C4 C5 C6 C1 0.6(13) . . . . ? C2 C1 C6 C5 -0.5(12) . . . . ? As1 C1 C6 C5 -176.6(6) . . . . ? C13 As1 C7 C8 -140.6(6) . . . . ? C1 As1 C7 C8 95.8(6) . . . . ? Br1 As1 C7 C8 -21.2(6) . . . . ? C13 As1 C7 C12 43.8(7) . . . . ? C1 As1 C7 C12 -79.8(6) . . . . ? Br1 As1 C7 C12 163.3(5) . . . . ? C12 C7 C8 C9 0.1(11) . . . . ? As1 C7 C8 C9 -175.2(6) . . . . ? C7 C8 C9 C10 0.9(12) . . . . ? C8 C9 C10 C11 -0.4(12) . . . . ? C9 C10 C11 C12 -1.0(12) . . . . ? C10 C11 C12 C7 2.0(12) . . . . ? C8 C7 C12 C11 -1.6(11) . . . . ? As1 C7 C12 C11 173.9(6) . . . . ? C7 As1 C13 C14 -153.5(6) . . . . ? C1 As1 C13 C14 -30.3(7) . . . . ? Br1 As1 C13 C14 88.2(6) . . . . ? C7 As1 C13 C18 30.1(7) . . . . ? C1 As1 C13 C18 153.3(6) . . . . ? Br1 As1 C13 C18 -88.2(6) . . . . ? C18 C13 C14 C15 0.9(11) . . . . ? As1 C13 C14 C15 -175.4(6) . . . . ? C13 C14 C15 C16 -0.9(12) . . . . ? C14 C15 C16 C17 0.9(12) . . . . ? C15 C16 C17 C18 -0.9(12) . . . . ? C16 C17 C18 C13 0.9(12) . . . . ? C14 C13 C18 C17 -0.9(12) . . . . ? As1 C13 C18 C17 175.4(6) . . . . ? # END of CIF