# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1468 #============================================================================== data_global #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name ; Dr Robin G. Pritchard ; _publ_contact_author_address ; Department of Chemistry University of Manchester Institute of Science and Technology PO Box 88 Manchester M60 1QD England ; _publ_contact_author_phone '0161 200 4568' _publ_contact_author_fax '0161 236 7677' _publ_contact_author_email 'Robin.Pritchard@UMIST.AC.UK' _publ_requested_journal 'Chem. Soc., Dalton Trans.' _publ_author_name 'Godfrey, McAuliffe, Pritchard' _publ_section_title '**** Paper ref. 9/02433F Correction *****' data_sj3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H18 I2 N3 P S' _chemical_formula_weight 449.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 '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' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'C mc2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' '-x, y, z' '-x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' _cell_length_a 10.8780(13) _cell_length_b 9.0848(9) _cell_length_c 14.213(2) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1404.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.124 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 4.710 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 688 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0098 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 24.97 _reflns_number_total 688 _reflns_number_gt 680 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0658P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(6) _refine_ls_number_reflns 688 _refine_ls_number_parameters 67 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.186 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.0000 0.21104(7) 0.31735(4) 0.0283(2) Uani 1 2 d S . . I2 I 0.0000 0.00935(10) 0.47148(7) 0.0404(3) Uani 1 2 d S . . P1 P 0.0000 0.5959(3) 0.2254(2) 0.0198(6) Uani 1 2 d S . . S1 S 0.0000 0.3939(3) 0.1672(2) 0.0276(6) Uani 1 2 d S . . N1 N -0.1284(7) 0.6797(8) 0.1963(5) 0.0270(14) Uani 1 1 d . . . N2 N 0.0000 0.6086(10) 0.3382(7) 0.023(2) Uani 1 2 d S . . C1 C -0.1496(8) 0.8287(10) 0.2295(7) 0.035(2) Uani 1 1 d . . . H1A H -0.0768 0.8641 0.2617 0.052 Uiso 1 1 calc R . . H1B H -0.2187 0.8292 0.2727 0.052 Uiso 1 1 calc R . . H1C H -0.1675 0.8922 0.1764 0.052 Uiso 1 1 calc R . . C2 C -0.1953(8) 0.6456(10) 0.1087(6) 0.034(2) Uani 1 1 d . . . H2A H -0.1555 0.5640 0.0769 0.052 Uiso 1 1 calc R . . H2B H -0.1949 0.7312 0.0679 0.052 Uiso 1 1 calc R . . H2C H -0.2795 0.6192 0.1236 0.052 Uiso 1 1 calc R . . C3 C 0.1129(10) 0.5908(10) 0.3952(8) 0.044(2) Uani 1 1 d . . . H3A H 0.1663 0.5188 0.3657 0.066 Uiso 1 1 calc R . . H3B H 0.0911 0.5574 0.4579 0.066 Uiso 1 1 calc R . . H3C H 0.1554 0.6844 0.3995 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0235(4) 0.0260(4) 0.0354(4) -0.0024(3) 0.000 0.000 I2 0.0559(5) 0.0373(4) 0.0278(4) 0.0002(3) 0.000 0.000 P1 0.0158(13) 0.0260(13) 0.0177(12) 0.0021(11) 0.000 0.000 S1 0.0290(13) 0.0250(14) 0.0287(17) -0.0024(14) 0.000 0.000 N1 0.024(3) 0.035(3) 0.022(3) -0.001(3) -0.007(3) 0.003(3) N2 0.029(5) 0.027(4) 0.015(5) -0.004(3) 0.000 0.000 C1 0.021(4) 0.037(4) 0.046(5) -0.006(4) -0.004(4) 0.005(3) C2 0.031(5) 0.047(5) 0.026(5) 0.000(4) -0.015(4) 0.003(4) C3 0.051(6) 0.051(6) 0.029(4) 0.007(4) -0.012(5) 0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 S1 2.705(3) . ? I1 I2 2.8560(12) . ? P1 N2 1.608(10) . ? P1 N1 1.644(7) 3 ? P1 N1 1.644(7) . ? P1 S1 2.014(4) . ? N1 C1 1.451(10) . ? N1 C2 1.475(10) . ? N2 C3 1.481(11) . ? N2 C3 1.481(11) 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 S1 I1 I2 177.98(6) . . ? N2 P1 N1 102.6(3) . 3 ? N2 P1 N1 102.6(3) . . ? N1 P1 N1 116.4(5) 3 . ? N2 P1 S1 118.4(4) . . ? N1 P1 S1 108.6(3) 3 . ? N1 P1 S1 108.6(3) . . ? P1 S1 I1 103.61(17) . . ? C1 N1 C2 113.1(7) . . ? C1 N1 P1 119.0(6) . . ? C2 N1 P1 122.3(6) . . ? C3 N2 C3 112.1(11) . 3 ? C3 N2 P1 122.6(5) . . ? C3 N2 P1 122.6(5) 3 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.569 _refine_diff_density_min -1.475 _refine_diff_density_rms 0.195 #===END data_sg202a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Br I P S' _chemical_formula_weight 501.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.352(2) _cell_length_b 9.3856(10) _cell_length_c 15.298(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.47(2) _cell_angle_gamma 90.00 _cell_volume 1765.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'tablet' _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 4.280 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3158 _exptl_absorpt_correction_T_max 0.4142 _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3249 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3249 _reflns_number_gt 2660 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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 w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+1.0354P] 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_extinction_coef ? _refine_ls_number_reflns 3249 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.691796(19) 0.43367(3) 0.578441(16) 0.02951(11) Uani 0.888(4) d P . . Br1 Br 0.691796(19) 0.43367(3) 0.578441(16) 0.02951(11) Uani 0.112(4) d P . . Br2 Br 0.76304(3) 0.43959(5) 0.74967(3) 0.04105(15) Uani 1 d . . . S1 S 0.60964(9) 0.44544(11) 0.41169(7) 0.0368(3) Uani 1 d . . . P1 P 0.67048(8) 0.28052(10) 0.34867(6) 0.0260(2) Uani 1 d . . . C1 C 0.6394(3) 0.1090(4) 0.3922(2) 0.0253(8) Uani 1 d . . . C2 C 0.6950(3) 0.0644(4) 0.4710(3) 0.0355(9) Uani 1 d . . . H2 H 0.7507 0.1212 0.4991 0.043 Uiso 1 calc R . . C3 C 0.6680(4) -0.0630(5) 0.5074(3) 0.0410(10) Uani 1 d . . . H3 H 0.7051 -0.0926 0.5608 0.049 Uiso 1 calc R . . C4 C 0.5880(4) -0.1476(4) 0.4672(3) 0.0387(10) Uani 1 d . . . H4 H 0.5704 -0.2345 0.4929 0.046 Uiso 1 calc R . . C5 C 0.5333(4) -0.1049(4) 0.3889(3) 0.0398(10) Uani 1 d . . . H5 H 0.4789 -0.1634 0.3608 0.048 Uiso 1 calc R . . C6 C 0.5583(3) 0.0239(4) 0.3515(2) 0.0324(9) Uani 1 d . . . H6 H 0.5201 0.0534 0.2985 0.039 Uiso 1 calc R . . C7 C 0.8155(3) 0.2902(4) 0.3486(2) 0.0272(8) Uani 1 d . . . C8 C 0.8719(3) 0.4113(4) 0.3783(2) 0.0308(8) Uani 1 d . . . H8 H 0.8344 0.4890 0.3998 0.037 Uiso 1 calc R . . C9 C 0.9832(3) 0.4174(4) 0.3761(3) 0.0375(10) Uani 1 d . . . H9 H 1.0218 0.4982 0.3978 0.045 Uiso 1 calc R . . C10 C 1.0380(3) 0.3057(4) 0.3423(3) 0.0387(10) Uani 1 d . . . H10 H 1.1136 0.3114 0.3397 0.046 Uiso 1 calc R . . C11 C 0.9826(3) 0.1861(4) 0.3124(3) 0.0377(10) Uani 1 d . . . H11 H 1.0205 0.1104 0.2892 0.045 Uiso 1 calc R . . C12 C 0.8718(3) 0.1759(4) 0.3162(3) 0.0325(9) Uani 1 d . . . H12 H 0.8346 0.0925 0.2972 0.039 Uiso 1 calc R . . C13 C 0.6068(3) 0.2912(4) 0.2377(2) 0.0271(8) Uani 1 d . . . C14 C 0.4948(3) 0.3131(4) 0.2265(2) 0.0320(9) Uani 1 d . . . H14 H 0.4550 0.3213 0.2756 0.038 Uiso 1 calc R . . C15 C 0.4424(3) 0.3225(4) 0.1429(3) 0.0376(10) Uani 1 d . . . H15 H 0.3666 0.3351 0.1352 0.045 Uiso 1 calc R . . C16 C 0.5008(4) 0.3135(4) 0.0712(3) 0.0413(10) Uani 1 d . . . H16 H 0.4650 0.3225 0.0144 0.050 Uiso 1 calc R . . C17 C 0.6114(4) 0.2912(4) 0.0820(3) 0.0396(10) Uani 1 d . . . H17 H 0.6507 0.2828 0.0325 0.047 Uiso 1 calc R . . C18 C 0.6651(3) 0.2812(4) 0.1652(2) 0.0334(9) Uani 1 d . . . H18 H 0.7408 0.2676 0.1724 0.040 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02502(15) 0.03291(16) 0.02995(16) -0.00570(11) -0.00081(10) 0.00158(11) Br1 0.02502(15) 0.03291(16) 0.02995(16) -0.00570(11) -0.00081(10) 0.00158(11) Br2 0.0358(2) 0.0602(3) 0.0265(2) -0.00271(18) -0.00033(17) -0.0009(2) S1 0.0376(6) 0.0364(6) 0.0341(6) -0.0092(4) -0.0083(5) 0.0118(5) P1 0.0257(5) 0.0263(5) 0.0244(5) -0.0016(4) -0.0055(4) 0.0009(4) C1 0.0276(19) 0.0276(19) 0.0204(17) -0.0015(14) 0.0005(15) 0.0020(15) C2 0.038(2) 0.039(2) 0.028(2) -0.0019(18) -0.0071(17) 0.0044(19) C3 0.053(3) 0.043(2) 0.026(2) 0.0074(18) 0.0020(19) 0.013(2) C4 0.053(3) 0.026(2) 0.039(2) 0.0054(18) 0.018(2) 0.0041(19) C5 0.041(2) 0.037(2) 0.042(2) -0.0004(19) 0.009(2) -0.0076(19) C6 0.036(2) 0.035(2) 0.025(2) 0.0031(16) -0.0021(17) -0.0018(18) C7 0.0297(19) 0.0245(18) 0.0258(18) 0.0023(15) -0.0055(15) -0.0007(16) C8 0.036(2) 0.027(2) 0.028(2) -0.0020(16) -0.0032(17) 0.0000(17) C9 0.039(2) 0.034(2) 0.038(2) 0.0021(18) -0.0033(19) -0.0094(19) C10 0.028(2) 0.044(2) 0.043(2) 0.011(2) -0.0014(18) 0.0017(19) C11 0.034(2) 0.030(2) 0.050(3) 0.0044(19) 0.0040(19) 0.0050(18) C12 0.032(2) 0.0236(19) 0.041(2) -0.0040(16) 0.0011(18) -0.0033(16) C13 0.0315(19) 0.0230(18) 0.0246(18) 0.0018(15) -0.0084(16) -0.0032(16) C14 0.036(2) 0.033(2) 0.0256(19) 0.0027(16) -0.0042(16) 0.0073(18) C15 0.036(2) 0.041(2) 0.033(2) -0.0039(18) -0.0121(18) 0.0014(19) C16 0.054(3) 0.040(2) 0.027(2) 0.0010(18) -0.013(2) -0.008(2) C17 0.050(3) 0.043(2) 0.025(2) -0.0045(18) 0.0013(19) -0.009(2) C18 0.034(2) 0.033(2) 0.031(2) -0.0004(17) -0.0044(17) -0.0065(18) _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 S1 2.6564(11) . ? I1 Br2 2.6832(6) . ? S1 P1 2.0070(14) . ? P1 C7 1.794(4) . ? P1 C1 1.797(4) . ? P1 C13 1.804(4) . ? C1 C6 1.382(5) . ? C1 C2 1.395(5) . ? C2 C3 1.374(6) . ? C3 C4 1.367(6) . ? C4 C5 1.377(6) . ? C5 C6 1.385(5) . ? C7 C8 1.387(5) . ? C7 C12 1.395(5) . ? C8 C9 1.380(6) . ? C9 C10 1.374(6) . ? C10 C11 1.370(6) . ? C11 C12 1.378(5) . ? C13 C18 1.383(5) . ? C13 C14 1.394(5) . ? C14 C15 1.379(5) . ? C15 C16 1.372(6) . ? C16 C17 1.377(6) . ? C17 C18 1.381(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 S1 I1 Br2 175.13(2) . . ? P1 S1 I1 107.63(5) . . ? C7 P1 C1 107.11(17) . . ? C7 P1 C13 110.01(17) . . ? C1 P1 C13 107.99(16) . . ? C7 P1 S1 112.39(13) . . ? C1 P1 S1 114.21(12) . . ? C13 P1 S1 105.03(13) . . ? C6 C1 C2 119.5(3) . . ? C6 C1 P1 121.5(3) . . ? C2 C1 P1 118.9(3) . . ? C3 C2 C1 119.5(4) . . ? C4 C3 C2 121.1(4) . . ? C3 C4 C5 119.7(4) . . ? C4 C5 C6 120.2(4) . . ? C5 C6 C1 119.9(4) . . ? C8 C7 C12 119.7(4) . . ? C8 C7 P1 120.8(3) . . ? C12 C7 P1 119.5(3) . . ? C9 C8 C7 119.7(4) . . ? C10 C9 C8 120.4(4) . . ? C11 C10 C9 120.1(4) . . ? C10 C11 C12 120.6(4) . . ? C11 C12 C7 119.5(4) . . ? C18 C13 C14 119.9(3) . . ? C18 C13 P1 122.5(3) . . ? C14 C13 P1 117.6(3) . . ? C15 C14 C13 119.8(4) . . ? C16 C15 C14 120.2(4) . . ? C17 C16 C15 120.3(4) . . ? C16 C17 C18 120.3(4) . . ? C13 C18 C17 119.6(4) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.725 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.092 #===END data_sg204a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H18 Br3 N3 P S1.50' _chemical_formula_weight 451.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.429(2) _cell_length_b 9.972(2) _cell_length_c 19.282(4) _cell_angle_alpha 80.66(2) _cell_angle_beta 81.18(2) _cell_angle_gamma 74.33(2) _cell_volume 1529.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'orange-brown' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 8.198 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1615 _exptl_absorpt_correction_T_max 0.4944 _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5871 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.97 _reflns_number_total 5361 _reflns_number_gt 3372 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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 w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.9699P] 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_extinction_coef ? _refine_ls_number_reflns 5361 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.62549(11) 0.84849(11) 0.45041(5) 0.0524(3) Uani 1 d . . . Br2 Br 0.90945(10) 0.81018(8) 0.38297(4) 0.0334(2) Uani 1 d . . . Br3 Br 1.19440(11) 0.75794(10) 0.31251(5) 0.0519(3) Uani 1 d . . . Br4 Br 0.32607(11) 0.30479(10) 0.16992(5) 0.0492(3) Uani 1 d . . . Br5 Br 0.61976(10) 0.24343(9) 0.10632(4) 0.0384(2) Uani 1 d . . . Br6 Br 0.91163(12) 0.17137(11) 0.04613(5) 0.0545(3) Uani 1 d . . . S1 S 0.5826(2) 0.5287(2) 0.22702(11) 0.0330(5) Uani 1 d . . . S2 S 0.6230(3) 0.5790(2) 0.31968(11) 0.0398(6) Uani 1 d . . . S3 S 0.8762(3) 0.5201(2) 0.31900(12) 0.0404(6) Uani 1 d . . . P1 P 0.6098(2) 0.7041(2) 0.15215(10) 0.0259(5) Uani 1 d . . . P2 P 0.9114(2) 0.3107(2) 0.36220(10) 0.0249(5) Uani 1 d . . . N1 N 0.4305(8) 0.7773(7) 0.1267(3) 0.0327(16) Uani 1 d . . . N2 N 0.7421(8) 0.6326(8) 0.0911(3) 0.0388(18) Uani 1 d . . . N3 N 0.6745(7) 0.8184(6) 0.1835(3) 0.0284(15) Uani 1 d . . . N4 N 0.8495(7) 0.2142(6) 0.3178(3) 0.0298(15) Uani 1 d . . . N5 N 1.1111(8) 0.2595(7) 0.3571(4) 0.0341(16) Uani 1 d . . . N6 N 0.8058(8) 0.3061(7) 0.4391(3) 0.0311(16) Uani 1 d . . . C1 C 0.3202(10) 0.6905(11) 0.1190(5) 0.052(3) Uani 1 d . . . H1A H 0.3649 0.5946 0.1394 0.078 Uiso 1 calc R . . H1B H 0.3118 0.6926 0.0692 0.078 Uiso 1 calc R . . H1C H 0.2110 0.7271 0.1433 0.078 Uiso 1 calc R . . C2 C 0.3735(13) 0.9268(10) 0.1012(6) 0.068(3) Uani 1 d . . . H2A H 0.4528 0.9758 0.1092 0.103 Uiso 1 calc R . . H2B H 0.2663 0.9654 0.1265 0.103 Uiso 1 calc R . . H2C H 0.3637 0.9383 0.0510 0.103 Uiso 1 calc R . . C3 C 0.7145(11) 0.6610(12) 0.0167(5) 0.065(3) Uani 1 d . . . H3A H 0.6083 0.7281 0.0115 0.098 Uiso 1 calc R . . H3B H 0.7145 0.5745 -0.0001 0.098 Uiso 1 calc R . . H3C H 0.8022 0.6995 -0.0107 0.098 Uiso 1 calc R . . C4 C 0.8999(10) 0.5327(10) 0.1058(5) 0.053(3) Uani 1 d . . . H4A H 0.9083 0.5192 0.1562 0.080 Uiso 1 calc R . . H4B H 0.9910 0.5693 0.0804 0.080 Uiso 1 calc R . . H4C H 0.9047 0.4436 0.0905 0.080 Uiso 1 calc R . . C5 C 0.8420(10) 0.8369(10) 0.1679(5) 0.050(2) Uani 1 d . . . H5A H 0.9040 0.7775 0.1327 0.074 Uiso 1 calc R . . H5B H 0.8961 0.8112 0.2108 0.074 Uiso 1 calc R . . H5C H 0.8377 0.9343 0.1499 0.074 Uiso 1 calc R . . C6 C 0.5702(10) 0.9029(9) 0.2374(4) 0.041(2) Uani 1 d . . . H6A H 0.4619 0.8831 0.2464 0.062 Uiso 1 calc R . . H6B H 0.5579 1.0019 0.2206 0.062 Uiso 1 calc R . . H6C H 0.6222 0.8795 0.2808 0.062 Uiso 1 calc R . . C7 C 0.6821(9) 0.1956(8) 0.3303(4) 0.0330(19) Uani 1 d . . . H7A H 0.6306 0.2231 0.3761 0.050 Uiso 1 calc R . . H7B H 0.6860 0.0977 0.3295 0.050 Uiso 1 calc R . . H7C H 0.6180 0.2534 0.2936 0.050 Uiso 1 calc R . . C8 C 0.9396(10) 0.1748(9) 0.2506(4) 0.040(2) Uani 1 d . . . H8A H 1.0496 0.1907 0.2460 0.060 Uiso 1 calc R . . H8B H 0.8805 0.2313 0.2122 0.060 Uiso 1 calc R . . H8C H 0.9491 0.0763 0.2488 0.060 Uiso 1 calc R . . C9 C 1.2139(10) 0.3525(10) 0.3657(5) 0.049(2) Uani 1 d . . . H9A H 1.1483 0.4491 0.3615 0.074 Uiso 1 calc R . . H9B H 1.3080 0.3427 0.3293 0.074 Uiso 1 calc R . . H9C H 1.2533 0.3270 0.4119 0.074 Uiso 1 calc R . . C10 C 1.2011(10) 0.1111(8) 0.3630(5) 0.047(2) Uani 1 d . . . H10A H 1.1275 0.0548 0.3573 0.071 Uiso 1 calc R . . H10B H 1.2407 0.0825 0.4091 0.071 Uiso 1 calc R . . H10C H 1.2947 0.0976 0.3264 0.071 Uiso 1 calc R . . C11 C 0.8115(10) 0.1672(9) 0.4822(4) 0.040(2) Uani 1 d . . . H11A H 0.8383 0.0948 0.4511 0.059 Uiso 1 calc R . . H11B H 0.7044 0.1688 0.5094 0.059 Uiso 1 calc R . . H11C H 0.8957 0.1474 0.5141 0.059 Uiso 1 calc R . . C12 C 0.7654(13) 0.4165(10) 0.4846(5) 0.061(3) Uani 1 d . . . H12A H 0.7619 0.5063 0.4557 0.091 Uiso 1 calc R . . H12B H 0.8493 0.3980 0.5165 0.091 Uiso 1 calc R . . H12C H 0.6581 0.4189 0.5117 0.091 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0436(5) 0.0597(6) 0.0495(6) -0.0085(5) 0.0035(4) -0.0097(5) Br2 0.0379(5) 0.0280(4) 0.0371(5) -0.0092(4) -0.0090(4) -0.0073(4) Br3 0.0402(5) 0.0484(6) 0.0634(7) -0.0119(5) 0.0062(5) -0.0085(4) Br4 0.0492(6) 0.0521(6) 0.0467(6) -0.0026(5) -0.0015(4) -0.0177(5) Br5 0.0481(5) 0.0402(5) 0.0307(5) 0.0009(4) -0.0110(4) -0.0174(4) Br6 0.0506(6) 0.0653(7) 0.0448(6) -0.0019(5) -0.0044(4) -0.0136(5) S1 0.0399(11) 0.0280(11) 0.0322(12) 0.0024(9) -0.0122(9) -0.0095(9) S2 0.0519(13) 0.0325(12) 0.0278(12) -0.0040(9) -0.0096(10) 0.0043(10) S3 0.0541(14) 0.0240(11) 0.0487(14) 0.0066(10) -0.0266(11) -0.0143(10) P1 0.0256(10) 0.0294(11) 0.0236(11) -0.0034(9) -0.0047(8) -0.0076(8) P2 0.0292(10) 0.0218(10) 0.0256(11) -0.0021(8) -0.0085(8) -0.0072(8) N1 0.032(4) 0.036(4) 0.031(4) 0.003(3) -0.010(3) -0.011(3) N2 0.036(4) 0.056(5) 0.022(4) -0.007(3) -0.004(3) -0.006(3) N3 0.032(4) 0.026(3) 0.031(4) -0.003(3) -0.006(3) -0.012(3) N4 0.034(4) 0.029(4) 0.032(4) -0.004(3) -0.012(3) -0.014(3) N5 0.030(4) 0.030(4) 0.046(4) -0.001(3) -0.011(3) -0.013(3) N6 0.036(4) 0.028(4) 0.026(4) 0.000(3) -0.005(3) -0.006(3) C1 0.039(5) 0.078(7) 0.049(6) 0.010(5) -0.021(4) -0.031(5) C2 0.082(8) 0.038(6) 0.088(8) 0.009(5) -0.060(7) -0.001(5) C3 0.047(6) 0.108(9) 0.039(6) -0.009(6) -0.003(5) -0.016(6) C4 0.039(5) 0.054(6) 0.052(6) -0.008(5) 0.007(4) 0.008(5) C5 0.043(5) 0.054(6) 0.056(6) -0.003(5) -0.002(5) -0.024(5) C6 0.055(5) 0.034(5) 0.041(5) -0.011(4) -0.011(4) -0.015(4) C7 0.032(4) 0.032(5) 0.041(5) -0.003(4) -0.013(4) -0.014(4) C8 0.053(5) 0.043(5) 0.030(5) -0.011(4) -0.004(4) -0.021(4) C9 0.043(5) 0.055(6) 0.057(6) -0.006(5) -0.018(5) -0.020(5) C10 0.038(5) 0.027(5) 0.072(7) -0.004(4) -0.018(5) 0.003(4) C11 0.041(5) 0.041(5) 0.036(5) 0.000(4) -0.003(4) -0.013(4) C12 0.086(8) 0.045(6) 0.038(6) -0.011(5) 0.003(5) 0.005(5) _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 Br2 2.5056(14) . ? Br2 Br3 2.5376(14) . ? Br4 Br5 2.5496(14) . ? Br5 Br6 2.5210(15) . ? S1 S2 2.032(3) . ? S1 P1 2.119(3) . ? S2 S3 2.053(3) . ? S3 P2 2.079(3) . ? P1 N1 1.604(6) . ? P1 N2 1.605(7) . ? P1 N3 1.619(6) . ? P2 N6 1.609(7) . ? P2 N5 1.614(6) . ? P2 N4 1.615(6) . ? N1 C2 1.464(10) . ? N1 C1 1.467(11) . ? N2 C3 1.458(10) . ? N2 C4 1.466(9) . ? N3 C5 1.452(10) . ? N3 C6 1.473(9) . ? N4 C7 1.451(9) . ? N4 C8 1.453(9) . ? N5 C10 1.464(9) . ? N5 C9 1.472(10) . ? N6 C12 1.455(10) . ? N6 C11 1.488(10) . ? 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 Br1 Br2 Br3 176.51(5) . . ? Br6 Br5 Br4 177.38(5) . . ? S2 S1 P1 104.21(13) . . ? S1 S2 S3 104.66(13) . . ? S2 S3 P2 100.74(13) . . ? N1 P1 N2 113.2(3) . . ? N1 P1 N3 109.0(3) . . ? N2 P1 N3 111.6(4) . . ? N1 P1 S1 106.7(3) . . ? N2 P1 S1 102.5(3) . . ? N3 P1 S1 113.7(2) . . ? N6 P2 N5 118.6(3) . . ? N6 P2 N4 106.8(4) . . ? N5 P2 N4 107.8(3) . . ? N6 P2 S3 107.6(2) . . ? N5 P2 S3 101.5(3) . . ? N4 P2 S3 114.9(2) . . ? C2 N1 C1 115.3(7) . . ? C2 N1 P1 124.4(6) . . ? C1 N1 P1 119.8(6) . . ? C3 N2 C4 114.7(7) . . ? C3 N2 P1 122.7(6) . . ? C4 N2 P1 122.7(5) . . ? C5 N3 C6 113.8(7) . . ? C5 N3 P1 124.4(6) . . ? C6 N3 P1 121.4(5) . . ? C7 N4 C8 114.3(6) . . ? C7 N4 P2 122.4(5) . . ? C8 N4 P2 121.0(5) . . ? C10 N5 C9 113.0(6) . . ? C10 N5 P2 122.7(6) . . ? C9 N5 P2 122.4(5) . . ? C12 N6 C11 110.5(7) . . ? C12 N6 P2 125.3(6) . . ? C11 N6 P2 118.5(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.762 _refine_diff_density_min -0.767 _refine_diff_density_rms 0.139