Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Stephen Godfrey' _publ_contact_author_address ; School of Chemistry University of Manchester Chemistry Building Oxford Road Manchester Lancashire M13 9PL UNITED KINGDOM ; _publ_contact_author_email STEPHEN.GODFREY@MANCHESTER.AC.UK _publ_section_title ; Preference for a C3 conformation in tris-dimethylaminophosphonium cations: A comparison of the reactions of (Me2N)3P with I-X (X = Cl, Br, I, CN). ; _publ_requested_category FO loop_ _publ_author_name 'Stephen Godfrey' 'Nicholas A. Barnes' 'Ruth T. A. Halton' 'R. Pritchard' 'Zaki Safi' ; J.M.Sheffield ; data_zak4u _database_code_depnum_ccdc_archive 'CCDC 644010' _audit_creation_date 2006-07-21T14:13:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C38 H111 I12 N19 P6' _chemical_formula_sum 'C38 H111 I12 N19 P6' _chemical_formula_weight 2543.08 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 3 c 1' _symmetry_space_group_name_Hall 'P 3 -2"c' _symmetry_Int_Tables_number 158 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' 'x, x-y, z+1/2' '-x+y, y, z+1/2' _cell_length_a 14.0028(10) _cell_length_b 14.0028(10) _cell_length_c 24.578(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 4173.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11 _cell_measurement_theta_max 15 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 2.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2396 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.605 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.7682 _exptl_absorpt_correction_T_max 0.9998 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 -12 -8 8 0 0 6 0 _diffrn_reflns_av_R_equivalents 0.078 _diffrn_reflns_av_unetI/netI 0.0644 _diffrn_reflns_number 4917 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4917 _reflns_number_gt 4377 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+71.8128P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4917 _refine_ls_number_parameters 149 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.128 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.008 _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 0.41(8) _refine_diff_density_max 1.006 _refine_diff_density_min -1.216 _refine_diff_density_rms 0.163 #----------------------------------------------------------------------------# # 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' N N 0.0061 0.0033 '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 I1 I 0.50533(7) 0.00921(7) 0.85008(4) 0.03726(17) Uani 1 1 d . . . I2 I 0 0 0.01141(5) 0.0453(4) Uani 1 3 d S . . I3 I 0.6667 0.3333 0.78211(7) 0.0415(4) Uani 1 3 d S . . I4 I 0.3333 -0.3333 0.79256(7) 0.0519(5) Uani 1 3 d S . . I5 I 0.71288(6) 0.02514(7) 0.75566(3) 0.0423(2) Uani 1 1 d . . . I6 I 0.63039(7) 0.98007(8) 0.03773(3) 0.0474(3) Uani 1 1 d . . . P1 P 0.3579(2) -0.0014(3) 0.90631(11) 0.0288(8) Uani 1 1 d . . . P2 P 0 0 0.11100(18) 0.0225(11) Uani 1 3 d S . . P3 P 0.6667 0.3333 0.6830(2) 0.0299(14) Uani 1 3 d S . . P4 P 0.3333 -0.3333 0.6935(2) 0.0266(13) Uani 1 3 d S . . N1 N 0.3850(8) 0.1180(9) 0.9234(4) 0.033(3) Uiso 1 1 d . . . N2 N 0.3472(9) -0.0720(9) 0.9604(4) 0.036(3) Uiso 1 1 d . . . N3 N 0.2447(8) -0.0606(8) 0.8711(4) 0.030(2) Uiso 1 1 d . . . N4 N -0.0721(8) 0.0540(8) 0.1313(4) 0.031(2) Uiso 1 1 d . . . N5 N 0.5929(9) 0.2077(10) 0.6632(4) 0.038(3) Uiso 1 1 d . . . N6 N 0.4572(9) -0.2753(9) 0.6738(4) 0.037(3) Uiso 1 1 d . . . N7 N 0 0 0.8730(10) 0.065(6) Uiso 1 3 d S . . C1 C 0.3131(17) 0.1675(16) 0.9048(8) 0.075(6) Uiso 1 1 d . . . H1A H 0.303 0.2057 0.9347 0.112 Uiso 1 1 calc R . . H1B H 0.2426 0.1092 0.8928 0.112 Uiso 1 1 calc R . . H1C H 0.3491 0.2181 0.8754 0.112 Uiso 1 1 calc R . . C2 C 0.4962(14) 0.2017(14) 0.9453(7) 0.061(5) Uiso 1 1 d . . . H2A H 0.4875 0.2256 0.9806 0.092 Uiso 1 1 calc R . . H2B H 0.5299 0.2638 0.9212 0.092 Uiso 1 1 calc R . . H2C H 0.542 0.1689 0.9481 0.092 Uiso 1 1 calc R . . C3 C 0.3401(11) -0.1792(11) 0.9578(5) 0.039(3) Uiso 1 1 d . . . H3A H 0.391 -0.1812 0.9834 0.059 Uiso 1 1 calc R . . H3B H 0.3582 -0.1912 0.9218 0.059 Uiso 1 1 calc R . . H3C H 0.2665 -0.2358 0.9667 0.059 Uiso 1 1 calc R . . C4 C 0.3331(13) -0.0367(12) 1.0161(5) 0.048(4) Uiso 1 1 d . . . H4A H 0.2583 -0.0826 1.0278 0.071 Uiso 1 1 calc R . . H4B H 0.3503 0.0387 1.0149 0.071 Uiso 1 1 calc R . . H4C H 0.3819 -0.0438 1.0411 0.071 Uiso 1 1 calc R . . C5 C 0.1447(15) -0.1516(14) 0.8913(7) 0.063(5) Uiso 1 1 d . . . H5A H 0.0845 -0.1389 0.8845 0.095 Uiso 1 1 calc R . . H5B H 0.1514 -0.1592 0.9297 0.095 Uiso 1 1 calc R . . H5C H 0.1311 -0.218 0.8731 0.095 Uiso 1 1 calc R . . C6 C 0.2425(12) -0.0259(13) 0.8147(5) 0.047(4) Uiso 1 1 d . . . H6A H 0.2528 -0.073 0.79 0.071 Uiso 1 1 calc R . . H6B H 0.3007 0.0489 0.8098 0.071 Uiso 1 1 calc R . . H6C H 0.1728 -0.0309 0.8077 0.071 Uiso 1 1 calc R . . C7 C -0.0541(10) 0.1569(10) 0.1059(6) 0.037(3) Uiso 1 1 d . . . H7A H -0.1158 0.1415 0.0831 0.055 Uiso 1 1 calc R . . H7B H 0.0119 0.1881 0.0844 0.055 Uiso 1 1 calc R . . H7C H -0.0466 0.2083 0.1338 0.055 Uiso 1 1 calc R . . C8 C -0.1701(9) -0.0032(12) 0.1608(5) 0.031(3) Uiso 1 1 d . . . H8A H -0.1718 0.0438 0.1888 0.046 Uiso 1 1 calc R . . H8B H -0.1742 -0.0674 0.177 0.046 Uiso 1 1 calc R . . H8C H -0.2318 -0.0251 0.1368 0.046 Uiso 1 1 calc R . . C9 C 0.4837(10) 0.1360(10) 0.6874(5) 0.032(3) Uiso 1 1 d . . . H9A H 0.486 0.0803 0.7091 0.047 Uiso 1 1 calc R . . H9B H 0.4301 0.1016 0.659 0.047 Uiso 1 1 calc R . . H9C H 0.4636 0.1793 0.7098 0.047 Uiso 1 1 calc R . . C10 C 0.6370(13) 0.1599(13) 0.6279(6) 0.048(4) Uiso 1 1 d . . . H10A H 0.5842 0.1188 0.6 0.073 Uiso 1 1 calc R . . H10B H 0.6536 0.1114 0.6483 0.073 Uiso 1 1 calc R . . H10C H 0.7033 0.217 0.6115 0.073 Uiso 1 1 calc R . . C11 C 0.5131(13) -0.1832(13) 0.6338(6) 0.051(4) Uiso 1 1 d . . . H11A H 0.5686 -0.1185 0.652 0.077 Uiso 1 1 calc R . . H11B H 0.4597 -0.1677 0.6178 0.077 Uiso 1 1 calc R . . H11C H 0.5467 -0.2042 0.6058 0.077 Uiso 1 1 calc R . . C12 C 0.5333(12) -0.3071(13) 0.6973(6) 0.049(4) Uiso 1 1 d . . . H12A H 0.5614 -0.3335 0.669 0.074 Uiso 1 1 calc R . . H12B H 0.495 -0.3643 0.7237 0.074 Uiso 1 1 calc R . . H12C H 0.5933 -0.2443 0.7146 0.074 Uiso 1 1 calc R . . C13 C 0 0 0.8302(7) 0.039(5) Uiso 1 3 d SD . . C14 C 0 0 0.7733(8) 0.032(5) Uiso 1 3 d S . . H14 H -0.019(8) -0.081(4) 0.7614(15) 0.034 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0268(3) 0.0396(4) 0.0461(3) -0.0009(4) 0.0062(4) 0.0171(3) I2 0.0535(5) 0.0535(5) 0.0290(6) 0 0 0.0267(3) I3 0.0426(5) 0.0426(5) 0.0392(8) 0 0 0.0213(2) I4 0.0607(7) 0.0607(7) 0.0343(8) 0 0 0.0303(3) I5 0.0412(3) 0.0481(4) 0.0425(4) 0.0019(4) 0.0058(4) 0.0261(3) I6 0.0454(4) 0.0551(5) 0.0421(4) -0.0039(6) -0.0013(5) 0.0255(4) P1 0.0273(13) 0.0233(13) 0.0349(14) -0.0031(13) 0.0011(13) 0.0120(11) P2 0.0204(12) 0.0204(12) 0.027(2) 0 0 0.0102(6) P3 0.0230(17) 0.0230(17) 0.044(3) 0 0 0.0115(8) P4 0.0233(17) 0.0233(17) 0.033(3) 0 0 0.0116(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 P1 2.427(3) . ? I2 P2 2.448(5) . ? I3 P3 2.436(6) . ? I4 P4 2.435(6) . ? P1 N1 1.576(12) . ? P1 N2 1.618(11) . ? P1 N3 1.624(10) . ? P2 N4 1.613(12) 3 ? P2 N4 1.613(12) 2 ? P2 N4 1.613(12) . ? P3 N5 1.607(11) 2_655 ? P3 N5 1.607(11) . ? P3 N5 1.607(11) 3_665 ? P4 N6 1.579(11) 2_545 ? P4 N6 1.579(11) 3_655 ? P4 N6 1.579(11) . ? N1 C2 1.504(19) . ? N1 C1 1.55(3) . ? N2 C3 1.454(18) . ? N2 C4 1.501(17) . ? N3 C5 1.431(19) . ? N3 C6 1.473(16) . ? N4 C8 1.398(14) . ? N4 C7 1.471(17) . ? N5 C10 1.41(2) . ? N5 C9 1.471(16) . ? N6 C12 1.46(2) . ? N6 C11 1.495(18) . ? N7 C13 1.05(3) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 C14 1.40(3) . ? C14 H14 1.07(5) . ? 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 N1 P1 N2 109.2(6) . . ? N1 P1 N3 109.9(6) . . ? N2 P1 N3 110.9(5) . . ? N1 P1 I1 109.9(4) . . ? N2 P1 I1 108.7(5) . . ? N3 P1 I1 108.1(4) . . ? N4 P2 N4 110.9(4) 3 2 ? N4 P2 N4 110.9(4) 3 . ? N4 P2 N4 110.9(4) 2 . ? N4 P2 I2 108.0(4) 3 . ? N4 P2 I2 108.0(4) 2 . ? N4 P2 I2 108.0(4) . . ? N5 P3 N5 111.2(4) 2_655 . ? N5 P3 N5 111.2(4) 2_655 3_665 ? N5 P3 N5 111.2(4) . 3_665 ? N5 P3 I3 107.7(4) 2_655 . ? N5 P3 I3 107.7(4) . . ? N5 P3 I3 107.7(4) 3_665 . ? N6 P4 N6 111.1(4) 2_545 3_655 ? N6 P4 N6 111.1(4) 2_545 . ? N6 P4 N6 111.1(4) 3_655 . ? N6 P4 I4 107.8(4) 2_545 . ? N6 P4 I4 107.8(4) 3_655 . ? N6 P4 I4 107.8(4) . . ? C2 N1 C1 114.1(13) . . ? C2 N1 P1 121.9(12) . . ? C1 N1 P1 122.0(10) . . ? C3 N2 C4 115.2(11) . . ? C3 N2 P1 122.2(9) . . ? C4 N2 P1 122.3(10) . . ? C5 N3 C6 116.6(11) . . ? C5 N3 P1 122.7(10) . . ? C6 N3 P1 120.6(8) . . ? C8 N4 C7 114.8(11) . . ? C8 N4 P2 123.9(10) . . ? C7 N4 P2 119.2(8) . . ? C10 N5 C9 118.4(11) . . ? C10 N5 P3 120.7(9) . . ? C9 N5 P3 120.3(10) . . ? C12 N6 C11 112.0(11) . . ? C12 N6 P4 120.2(9) . . ? C11 N6 P4 127.7(11) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 H7A 109.5 . . ? N4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C10 H10A 109.5 . . ? N5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N6 C11 H11A 109.5 . . ? N6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N6 C12 H12A 109.5 . . ? N6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N7 C13 C14 180.000(13) . . ? C13 C14 H14 106(3) . . ? # Attachment 'Compound_2.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-07-21 at 12:06:05 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : smg34c dreduc sortav struct data_smg34c _database_code_depnum_ccdc_archive 'CCDC 644011' _audit_creation_date 2006-07-21T12:06:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H18 Cl1 I1 N3 P1' _chemical_formula_sum 'C6 H18 Cl I N3 P' _chemical_formula_weight 325.55 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R3m _symmetry_space_group_name_Hall R3-2" _symmetry_Int_Tables_number 160 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-y, -x, z' '-x+y, -x, z' 'x, x-y, z' '-x+y, y, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-y+1/3, -x+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' _cell_length_a 8.2595(4) _cell_length_b 8.2595(4) _cell_length_c 16.5475(8) _cell_angle_alpha 90.000(2) _cell_angle_beta 90.000(2) _cell_angle_gamma 120.000(2) _cell_volume 977.62(8) _cell_formula_units_Z 3 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2610 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.6833 _exptl_absorpt_correction_T_max 0.7706 #----------------------------------------------------------------------------# # 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 0.151761E-1 _diffrn_orient_matrix_ub_12 0.965876E-1 _diffrn_orient_matrix_ub_13 -0.404467E-1 _diffrn_orient_matrix_ub_21 -0.136693 _diffrn_orient_matrix_ub_22 -0.440896E-1 _diffrn_orient_matrix_ub_23 0.37178E-2 _diffrn_orient_matrix_ub_31 0.250593E-1 _diffrn_orient_matrix_ub_32 0.909515E-1 _diffrn_orient_matrix_ub_33 0.447469E-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 0.0434 _diffrn_reflns_av_unetI/netI 0.0393 _diffrn_reflns_number 2362 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.38 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 592 _reflns_number_gt 577 _reflns_threshold_expression >2sigma(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, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0064P)^2^+0.8871P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0069(6) _refine_ls_number_reflns 592 _refine_ls_number_parameters 52 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.043 _refine_ls_wR_factor_gt 0.0417 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.112 _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 0.17(3) _refine_diff_density_max 0.372 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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 Cl1 Cl 0.6667 0.3333 0.00710(9) 0.0262(4) Uani 1 6 d S . . I1 I 0 0 0 0.0360(2) Uani 1 6 d S . . P1 P 0.6667 0.3333 -0.11556(9) 0.0165(3) Uani 1 6 d S . . N1 N 0.5066(6) 0.1297(7) -0.1440(3) 0.0240(10) Uani 0.5 1 d PD . . C1 C 0.4816(3) -0.0368(7) -0.1066(3) 0.0373(11) Uani 1 2 d SD . . C2 C 0.3488(10) 0.0985(10) -0.1971(4) 0.0313(13) Uani 0.5 1 d PD . . H1A H 0.401(5) -0.054(5) -0.0684(19) 0.052(8) Uiso 1 1 d D . . H1B H 0.440(3) -0.121(5) -0.146(3) 0.052(8) Uiso 1 2 d SD . . H2A H 0.351(9) 0.032(10) -0.235(3) 0.052(8) Uiso 0.5 1 d PD . . H2B H 0.255(5) 0.057(10) -0.167(3) 0.052(8) Uiso 0.5 1 d PD . . H2C H 0.391(7) 0.196(4) -0.224(3) 0.052(8) Uiso 1 2 d SD . . 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 Cl1 0.0308(6) 0.0308(6) 0.0169(7) 0 0 0.0154(3) I1 0.0411(2) 0.0411(2) 0.0258(2) 0 0 0.02054(12) P1 0.0171(5) 0.0171(5) 0.0151(7) 0 0 0.0086(3) N1 0.023(2) 0.022(2) 0.025(2) -0.0018(17) -0.0100(17) 0.0095(18) C1 0.044(2) 0.023(2) 0.038(3) -0.003(2) -0.0013(10) 0.0115(12) C2 0.028(3) 0.035(3) 0.029(3) -0.010(3) -0.010(3) 0.014(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 P1 2.030(2) . ? P1 N1 1.605(5) 2_655 ? P1 N1 1.605(5) 6_655 ? P1 N1 1.605(5) . ? P1 N1 1.605(5) 3_665 ? P1 N1 1.605(5) 4_665 ? P1 N1 1.605(5) 5 ? N1 N1 0.963(9) 6_655 ? N1 C1 1.427(7) . ? N1 C2 1.483(8) . ? C1 N1 1.427(7) 6_655 ? C1 H1A 0.88(3) . ? C1 H1B 0.88(3) . ? C2 C2 1.254(15) 5 ? C2 H2A 0.84(4) . ? C2 H2B 0.84(3) . ? C2 H2C 0.82(3) . ? 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 N1 P1 N1 79.0(3) 2_655 6_655 ? N1 P1 N1 111.76(15) 2_655 . ? N1 P1 N1 34.9(3) 6_655 . ? N1 P1 N1 34.9(3) 2_655 3_665 ? N1 P1 N1 111.76(15) 6_655 3_665 ? N1 P1 N1 138.8(3) . 3_665 ? N1 P1 N1 111.76(15) 2_655 4_665 ? N1 P1 N1 138.8(3) 6_655 4_665 ? N1 P1 N1 111.76(15) . 4_665 ? N1 P1 N1 79.0(3) 3_665 4_665 ? N1 P1 N1 138.8(3) 2_655 5 ? N1 P1 N1 111.76(15) 6_655 5 ? N1 P1 N1 79.0(3) . 5 ? N1 P1 N1 111.76(15) 3_665 5 ? N1 P1 N1 34.9(3) 4_665 5 ? N1 P1 Cl1 107.08(17) 2_655 . ? N1 P1 Cl1 107.08(17) 6_655 . ? N1 P1 Cl1 107.08(17) . . ? N1 P1 Cl1 107.08(17) 3_665 . ? N1 P1 Cl1 107.08(17) 4_665 . ? N1 P1 Cl1 107.08(17) 5 . ? N1 N1 C1 70.27(19) 6_655 . ? N1 N1 C2 142.3(3) 6_655 . ? C1 N1 C2 113.5(4) . . ? N1 N1 P1 72.54(16) 6_655 . ? C1 N1 P1 121.9(3) . . ? C2 N1 P1 123.2(4) . . ? N1 C1 N1 39.5(4) . 6_655 ? N1 C1 H1A 102(2) . . ? N1 C1 H1A 131(2) 6_655 . ? N1 C1 H1B 104(3) . . ? N1 C1 H1B 104(3) 6_655 . ? H1A C1 H1B 116(3) . . ? C2 C2 N1 105.4(3) 5 . ? C2 C2 H2A 131(5) 5 . ? N1 C2 H2A 105(3) . . ? C2 C2 H2B 87(5) 5 . ? N1 C2 H2B 106(4) . . ? H2A C2 H2B 120(7) . . ? C2 C2 H2C 40(3) 5 . ? N1 C2 H2C 104(3) . . ? H2A C2 H2C 96(6) . . ? H2B C2 H2C 125(6) . . ? # Attachment 'Compound_4.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-03-26 at 16:31:04 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : new dreduc sortav struct data_new _database_code_depnum_ccdc_archive 'CCDC 644012' _audit_creation_date 2007-03-26T16:31:04-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H18 I1 N4 P1' _chemical_formula_sum 'C7 H18 I N4 P' _chemical_formula_weight 316.12 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 23.2367(4) _cell_length_b 8.22590(10) _cell_length_c 13.8563(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2648.53(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3206 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.51 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.6749 _exptl_absorpt_correction_T_max 0.7698 #----------------------------------------------------------------------------# # 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 -0.108061 _diffrn_orient_matrix_ub_12 0.81277E-2 _diffrn_orient_matrix_ub_13 -0.01911 _diffrn_orient_matrix_ub_21 0.347608E-1 _diffrn_orient_matrix_ub_22 -0.448115E-1 _diffrn_orient_matrix_ub_23 -0.314098E-1 _diffrn_orient_matrix_ub_31 -0.435112E-1 _diffrn_orient_matrix_ub_32 -0.559847E-1 _diffrn_orient_matrix_ub_33 0.223668E-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 0.050 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_number 3080 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 28.04 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.92 _diffrn_measured_fraction_theta_max 0.92 _reflns_number_total 3080 _reflns_number_gt 2529 _reflns_threshold_expression >2sigma(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, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0224P)^2^+5.1394P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3080 _refine_ls_number_parameters 247 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.06(3) _refine_diff_density_max 0.586 _refine_diff_density_min -0.836 _refine_diff_density_rms 0.086 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 0.8367(4) 0.4967(15) 0.6121(6) 0.065(2) Uani 1 1 d . . . H1A H 0.8788 0.5036 0.6126 0.098 Uiso 1 1 calc R . . H1B H 0.824 0.417 0.6603 0.098 Uiso 1 1 calc R . . H1C H 0.8203 0.6034 0.6277 0.098 Uiso 1 1 calc R . . C2 C 0.8393(4) 0.2872(9) 0.4865(6) 0.064(2) Uani 1 1 d . . . H2A H 0.8303 0.206 0.5359 0.096 Uiso 1 1 calc R . . H2B H 0.8811 0.2937 0.478 0.096 Uiso 1 1 calc R . . H2C H 0.8213 0.2558 0.4253 0.096 Uiso 1 1 calc R . . C3 C 0.7153(3) 0.8076(9) 0.5223(6) 0.0524(17) Uani 1 1 d . . . H3A H 0.7032 0.892 0.4768 0.079 Uiso 1 1 calc R . . H3B H 0.7235 0.8572 0.5852 0.079 Uiso 1 1 calc R . . H3C H 0.6845 0.7271 0.5295 0.079 Uiso 1 1 calc R . . C4 C 0.8177(3) 0.8360(9) 0.4752(7) 0.060(2) Uani 1 1 d . . . H4A H 0.8248 0.8928 0.5362 0.09 Uiso 1 1 calc R . . H4B H 0.8101 0.9158 0.4242 0.09 Uiso 1 1 calc R . . H4C H 0.8516 0.7713 0.458 0.09 Uiso 1 1 calc R . . C5 C 0.6684(3) 0.5017(14) 0.3755(6) 0.057(2) Uani 1 1 d . . . H5A H 0.6322 0.5349 0.4057 0.086 Uiso 1 1 calc R . . H5B H 0.6616 0.4082 0.3332 0.086 Uiso 1 1 calc R . . H5C H 0.6839 0.5921 0.3375 0.086 Uiso 1 1 calc R . . C6 C 0.6918(3) 0.3240(10) 0.5133(7) 0.0569(19) Uani 1 1 d . . . H6A H 0.6888 0.2237 0.4755 0.085 Uiso 1 1 calc R . . H6B H 0.6543 0.3499 0.5416 0.085 Uiso 1 1 calc R . . H6C H 0.7202 0.3093 0.5649 0.085 Uiso 1 1 calc R . . C7 C 0.7985(3) 0.5414(8) 0.3316(6) 0.0407(15) Uani 1 1 d . . . C8 C 0.4354(4) 1.2591(9) 0.7476(8) 0.062(2) Uani 1 1 d . . . H8A H 0.4412 1.3444 0.796 0.094 Uiso 1 1 calc R . . H8B H 0.3941 1.2464 0.735 0.094 Uiso 1 1 calc R . . H8C H 0.4551 1.2893 0.6877 0.094 Uiso 1 1 calc R . . C9 C 0.4392(4) 1.0583(9) 0.8802(5) 0.0502(18) Uani 1 1 d . . . H9A H 0.3972 1.0458 0.8797 0.075 Uiso 1 1 calc R . . H9B H 0.4499 1.143 0.9266 0.075 Uiso 1 1 calc R . . H9C H 0.4571 0.9552 0.8989 0.075 Uiso 1 1 calc R . . C10 C 0.5834(3) 1.2234(9) 0.7509(8) 0.067(2) Uani 1 1 d . . . H10A H 0.5814 1.3162 0.7067 0.1 Uiso 1 1 calc R . . H10B H 0.6234 1.2071 0.7713 0.1 Uiso 1 1 calc R . . H10C H 0.5594 1.2448 0.8076 0.1 Uiso 1 1 calc R . . C11 C 0.5988(3) 1.0182(11) 0.6221(6) 0.063(2) Uani 1 1 d . . . H11A H 0.6386 1.0069 0.6445 0.094 Uiso 1 1 calc R . . H11B H 0.5974 1.0962 0.5687 0.094 Uiso 1 1 calc R . . H11C H 0.5846 0.9124 0.5999 0.094 Uiso 1 1 calc R . . C12 C 0.4511(3) 0.7146(8) 0.7521(7) 0.0464(15) Uani 1 1 d . . . H12A H 0.4467 0.6589 0.8142 0.07 Uiso 1 1 calc R . . H12B H 0.454 0.6338 0.7003 0.07 Uiso 1 1 calc R . . H12C H 0.4176 0.7844 0.7406 0.07 Uiso 1 1 calc R . . C13 C 0.5570(3) 0.7288(10) 0.7797(7) 0.060(3) Uani 1 1 d . . . H13A H 0.5648 0.6437 0.7319 0.089 Uiso 1 1 calc R . . H13B H 0.5527 0.6794 0.8436 0.089 Uiso 1 1 calc R . . H13C H 0.5891 0.8061 0.7808 0.089 Uiso 1 1 calc R . . C14 C 0.4656(3) 0.9958(8) 0.6009(5) 0.0387(14) Uani 1 1 d . . . I1 I 0.78052(2) 1.05371(7) 0.75349(4) 0.06391(16) Uani 1 1 d . . . I2 I 1.01580(2) 0.50157(9) 0.51677(4) 0.06266(16) Uani 1 1 d . . . N1 N 0.8172(2) 0.4463(6) 0.5168(4) 0.0392(12) Uani 1 1 d . . . N2 N 0.7673(2) 0.7276(6) 0.4859(4) 0.0400(13) Uani 1 1 d . . . N3 N 0.7099(2) 0.4566(7) 0.4507(4) 0.0385(12) Uani 1 1 d . . . N4 N 0.8128(3) 0.5446(7) 0.2552(7) 0.0556(14) Uani 1 1 d . . . N5 N 0.4590(2) 1.1047(6) 0.7838(4) 0.0416(13) Uani 1 1 d . . . N6 N 0.5626(2) 1.0766(7) 0.7016(4) 0.0432(13) Uani 1 1 d . . . N7 N 0.5036(2) 0.8147(5) 0.7538(5) 0.0375(11) Uani 1 1 d . . . N8 N 0.4441(2) 0.9951(8) 0.5263(6) 0.0521(14) Uani 1 1 d . . . P1 P 0.77121(6) 0.54304(18) 0.45480(11) 0.0303(3) Uani 1 1 d . . . P2 P 0.50030(7) 0.9986(2) 0.71790(11) 0.0304(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 0.069(5) 0.071(5) 0.056(5) -0.005(5) -0.025(4) 0.011(5) C2 0.076(5) 0.049(4) 0.067(5) -0.001(4) 0.004(5) 0.028(4) C3 0.054(4) 0.051(4) 0.053(4) -0.006(4) 0.004(4) 0.016(3) C4 0.063(5) 0.044(4) 0.074(5) -0.012(4) 0.006(4) -0.014(4) C5 0.030(3) 0.098(6) 0.043(4) 0.008(4) -0.012(3) -0.007(4) C6 0.053(4) 0.060(5) 0.058(5) 0.010(4) 0.001(4) -0.015(3) C7 0.028(3) 0.042(4) 0.052(4) -0.006(3) -0.001(3) -0.002(3) C8 0.084(6) 0.048(4) 0.055(5) 0.012(5) 0.019(5) 0.028(4) C9 0.053(4) 0.058(4) 0.039(4) -0.003(3) 0.010(3) 0.001(4) C10 0.062(5) 0.064(5) 0.074(5) -0.023(6) -0.004(5) -0.028(4) C11 0.036(4) 0.089(6) 0.064(5) -0.019(5) 0.021(4) -0.018(4) C12 0.037(3) 0.041(3) 0.061(4) 0.011(4) -0.008(4) -0.007(3) C13 0.042(4) 0.052(4) 0.085(7) 0.017(4) -0.011(4) 0.006(3) C14 0.031(3) 0.038(3) 0.047(4) -0.002(3) 0.001(3) 0.001(3) I1 0.0666(3) 0.0753(3) 0.0499(3) -0.0003(3) -0.0053(3) -0.0127(3) I2 0.0624(3) 0.0739(3) 0.0517(3) -0.0039(3) 0.0177(3) -0.0058(3) N1 0.036(3) 0.048(3) 0.033(3) 0.003(3) -0.008(3) 0.010(2) N2 0.041(3) 0.029(3) 0.049(3) -0.005(2) 0.005(2) -0.001(2) N3 0.032(3) 0.049(3) 0.035(3) 0.004(2) -0.001(2) -0.008(2) N4 0.054(3) 0.066(4) 0.046(3) -0.002(4) 0.008(4) -0.003(3) N5 0.047(3) 0.041(3) 0.037(3) 0.003(2) 0.012(2) 0.011(3) N6 0.037(3) 0.050(3) 0.042(3) -0.006(3) 0.004(3) -0.012(2) N7 0.029(2) 0.033(2) 0.050(3) 0.005(3) 0.003(3) 0.001(2) N8 0.042(3) 0.070(4) 0.044(3) -0.002(3) -0.011(3) -0.002(3) P1 0.0259(7) 0.0350(8) 0.0299(8) -0.0020(6) -0.0001(6) 0.0008(6) P2 0.0287(7) 0.0314(7) 0.0310(7) 0.0003(6) 0.0009(6) -0.0002(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.458(10) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 N1 1.467(9) . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? C3 N2 1.465(8) . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 N2 1.480(9) . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 N3 1.465(9) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 N3 1.456(9) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 N4 1.111(11) . ? C7 P1 1.820(8) . ? C8 N5 1.472(8) . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 N5 1.463(8) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 N6 1.469(9) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 N6 1.467(9) . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 N7 1.473(7) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 N7 1.472(8) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 N8 1.148(10) . ? C14 P2 1.811(7) . ? N1 P1 1.584(5) . ? N2 P1 1.580(5) . ? N3 P1 1.594(5) . ? N5 P2 1.587(5) . ? N6 P2 1.600(5) . ? N7 P2 1.594(5) . ? 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 N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 P1 176.6(7) . . ? N5 C8 H8A 109.5 . . ? N5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N6 C10 H10A 109.5 . . ? N6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N6 C11 H11A 109.5 . . ? N6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N7 C12 H12A 109.5 . . ? N7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N7 C13 H13A 109.5 . . ? N7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N8 C14 P2 179.3(7) . . ? C1 N1 C2 113.8(6) . . ? C1 N1 P1 123.9(5) . . ? C2 N1 P1 122.0(5) . . ? C3 N2 C4 114.6(5) . . ? C3 N2 P1 125.0(4) . . ? C4 N2 P1 120.4(5) . . ? C6 N3 C5 115.1(6) . . ? C6 N3 P1 124.8(5) . . ? C5 N3 P1 120.0(5) . . ? C9 N5 C8 114.7(6) . . ? C9 N5 P2 124.9(5) . . ? C8 N5 P2 120.3(5) . . ? C11 N6 C10 115.5(6) . . ? C11 N6 P2 119.6(5) . . ? C10 N6 P2 124.2(5) . . ? C13 N7 C12 115.7(5) . . ? C13 N7 P2 124.9(4) . . ? C12 N7 P2 119.1(4) . . ? N2 P1 N1 111.9(3) . . ? N2 P1 N3 112.7(3) . . ? N1 P1 N3 113.5(3) . . ? N2 P1 C7 106.4(3) . . ? N1 P1 C7 105.6(3) . . ? N3 P1 C7 105.9(3) . . ? N5 P2 N7 111.8(3) . . ? N5 P2 N6 114.1(3) . . ? N7 P2 N6 112.4(3) . . ? N5 P2 C14 104.7(3) . . ? N7 P2 C14 106.8(3) . . ? N6 P2 C14 106.3(3) . . ? 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 C3 N2 P1 N1 -120.0(6) . . . . ? C4 N2 P1 N1 62.9(7) . . . . ? C3 N2 P1 N3 9.3(7) . . . . ? C4 N2 P1 N3 -167.8(6) . . . . ? C3 N2 P1 C7 125.0(6) . . . . ? C4 N2 P1 C7 -52.1(6) . . . . ? C1 N1 P1 N2 22.5(7) . . . . ? C2 N1 P1 N2 -164.1(6) . . . . ? C1 N1 P1 N3 -106.5(7) . . . . ? C2 N1 P1 N3 66.9(6) . . . . ? C1 N1 P1 C7 137.9(7) . . . . ? C2 N1 P1 C7 -48.7(6) . . . . ? C6 N3 P1 N2 -115.0(6) . . . . ? C5 N3 P1 N2 69.4(7) . . . . ? C6 N3 P1 N1 13.6(7) . . . . ? C5 N3 P1 N1 -162.0(6) . . . . ? C6 N3 P1 C7 129.1(6) . . . . ? C5 N3 P1 C7 -46.6(7) . . . . ? N4 C7 P1 N2 -61(11) . . . . ? N4 C7 P1 N1 18E1(10) . . . . ? N4 C7 P1 N3 59(11) . . . . ? C9 N5 P2 N7 16.7(7) . . . . ? C8 N5 P2 N7 -160.5(6) . . . . ? C9 N5 P2 N6 -112.3(6) . . . . ? C8 N5 P2 N6 70.5(7) . . . . ? C9 N5 P2 C14 131.9(6) . . . . ? C8 N5 P2 C14 -45.3(7) . . . . ? C13 N7 P2 N5 -123.6(7) . . . . ? C12 N7 P2 N5 63.2(7) . . . . ? C13 N7 P2 N6 6.3(8) . . . . ? C12 N7 P2 N6 -166.9(6) . . . . ? C13 N7 P2 C14 122.5(7) . . . . ? C12 N7 P2 C14 -50.7(7) . . . . ? C11 N6 P2 N5 -162.7(6) . . . . ? C10 N6 P2 N5 6.7(8) . . . . ? C11 N6 P2 N7 68.7(7) . . . . ? C10 N6 P2 N7 -122.0(7) . . . . ? C11 N6 P2 C14 -47.8(7) . . . . ? C10 N6 P2 C14 121.5(7) . . . . ? N8 C14 P2 N5 11E1(6) . . . . ? N8 C14 P2 N7 -13E1(6) . . . . ? N8 C14 P2 N6 -1E1(6) . . . . ? # Formatted by publCIF # Attachment 'Compound_3b.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-07-21 at 12:49:05 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : sg183b dreduc psi_scan struct data_sg183b _database_code_depnum_ccdc_archive 'CCDC 644013' _audit_creation_date 2006-07-21T12:49:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H18 Br0.50 Cl0.50 I1 N3 P1' _chemical_formula_sum 'C6 H18 Br0.50 Cl0.50 I N3 P' _chemical_formula_weight 347.78 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R 3 m' _symmetry_space_group_name_Hall 'R 3 -2' _symmetry_Int_Tables_number 160 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-y, -x, z' '-x+y, -x, z' 'x, x-y, z' '-x+y, y, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-y+1/3, -x+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' _cell_length_a 8.2719(9) _cell_length_b 8.2719(9) _cell_length_c 16.646(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 986.40(19) _cell_formula_units_Z 3 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 507 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.142 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.5755 _exptl_absorpt_correction_T_max 0.6822 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 5 -2 0 1 -7 5 -1 0 _diffrn_reflns_av_R_equivalents 0.1063 _diffrn_reflns_av_unetI/netI 0.0691 _diffrn_reflns_number 481 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.934 _diffrn_measured_fraction_theta_max 0.934 _reflns_number_total 230 _reflns_number_gt 230 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+0.7530P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0026(13) _refine_ls_number_reflns 230 _refine_ls_number_parameters 53 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.131 _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 0.13(15) _refine_diff_density_max 0.702 _refine_diff_density_min -0.63 _refine_diff_density_rms 0.106 #----------------------------------------------------------------------------# # 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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 Br1 Br 0.3333 0.6667 0.9865(2) 0.0278(9) Uani 0.51(2) 6 d SP . . Cl1 Cl 0.3333 0.6667 0.9865(2) 0.0278(9) Uani 0.49(2) 6 d SP . . I1 I 1 1 1 0.0342(4) Uani 1 6 d S . . P1 P 0.3333 0.6667 1.1143(3) 0.0180(9) Uani 1 6 d S . . N1 N 0.4858(15) 0.8663(14) 1.1423(8) 0.030(2) Uani 0.5 1 d PD . . C1 C 0.5182(7) 1.0363(14) 1.1045(8) 0.045(3) Uani 1 2 d SD . . C2 C 0.6493(18) 0.9095(18) 1.1946(11) 0.031(2) Uani 0.5 1 d PD . . H1A H 0.583(11) 1.031(10) 1.065(3) 0.037(15) Uiso 1 1 d D . . H1B H 0.554(5) 1.109(9) 1.142(4) 0.037(15) Uiso 1 2 d SD . . H2A H 0.652(17) 0.996(18) 1.220(9) 0.037(15) Uiso 0.5 1 d PD . . H2B H 0.730(9) 0.98(2) 1.162(5) 0.037(15) Uiso 0.5 1 d PD . . H2C H 0.606(12) 0.803(6) 1.214(5) 0.037(15) Uiso 1 2 d SD . . 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 0.0302(9) 0.0302(9) 0.0231(12) 0 0 0.0151(5) Cl1 0.0302(9) 0.0302(9) 0.0231(12) 0 0 0.0151(5) I1 0.0360(5) 0.0360(5) 0.0305(5) 0 0 0.0180(2) P1 0.0133(13) 0.0133(13) 0.0275(16) 0 0 0.0067(7) N1 0.029(5) 0.009(4) 0.046(4) -0.006(4) -0.015(4) 0.006(3) C1 0.056(5) 0.013(4) 0.054(6) -0.007(4) -0.003(2) 0.006(2) C2 0.023(6) 0.023(7) 0.046(6) 0.005(5) -0.005(5) 0.010(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 P1 2.127(9) . ? P1 N1 1.566(10) 6 ? P1 N1 1.566(10) 2_665 ? P1 N1 1.566(10) . ? P1 N1 1.566(10) 3_665 ? P1 N1 1.566(10) 5_565 ? P1 N1 1.566(10) 4_565 ? N1 N1 0.87(2) 6 ? N1 C1 1.439(14) . ? N1 C2 1.493(16) . ? C1 N1 1.439(15) 6 ? C1 H1A 0.86(5) . ? C1 H1B 0.81(5) . ? C2 C2 1.40(3) 5_565 ? C2 H2A 0.82(6) . ? C2 H2B 0.84(6) . ? C2 H2C 0.83(5) . ? 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 N1 P1 N1 81.3(8) 6 2_665 ? N1 P1 N1 32.3(9) 6 . ? N1 P1 N1 111.5(4) 2_665 . ? N1 P1 N1 111.5(4) 6 3_665 ? N1 P1 N1 32.3(9) 2_665 3_665 ? N1 P1 N1 136.8(9) . 3_665 ? N1 P1 N1 111.5(4) 6 5_565 ? N1 P1 N1 136.8(9) 2_665 5_565 ? N1 P1 N1 81.3(8) . 5_565 ? N1 P1 N1 111.5(4) 3_665 5_565 ? N1 P1 N1 136.8(9) 6 4_565 ? N1 P1 N1 111.5(4) 2_665 4_565 ? N1 P1 N1 111.5(4) . 4_565 ? N1 P1 N1 81.3(8) 3_665 4_565 ? N1 P1 N1 32.3(9) 5_565 4_565 ? N1 P1 Br1 107.4(4) 6 . ? N1 P1 Br1 107.4(4) 2_665 . ? N1 P1 Br1 107.4(4) . . ? N1 P1 Br1 107.4(4) 3_665 . ? N1 P1 Br1 107.4(4) 5_565 . ? N1 P1 Br1 107.4(4) 4_565 . ? N1 N1 C1 72.4(5) 6 . ? N1 N1 C2 141.8(9) 6 . ? C1 N1 C2 108.5(9) . . ? N1 N1 P1 73.9(4) 6 . ? C1 N1 P1 123.9(8) . . ? C2 N1 P1 125.6(8) . . ? N1 C1 N1 35.2(10) 6 . ? N1 C1 H1A 120(5) 6 . ? N1 C1 H1A 96(5) . . ? N1 C1 H1B 102(6) 6 . ? N1 C1 H1B 102(5) . . ? H1A C1 H1B 128(7) . . ? C2 C2 N1 102.3(6) 5_565 . ? C2 C2 H2A 149(10) 5_565 . ? N1 C2 H2A 98(5) . . ? C2 C2 H2B 109(10) 5_565 . ? N1 C2 H2B 95(5) . . ? H2A C2 H2B 92(10) . . ? C2 C2 H2C 33(6) 5_565 . ? N1 C2 H2C 96(5) . . ? H2A C2 H2C 122(10) . . ? H2B C2 H2C 142(10) . . ?