# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 186/1497 #======================================================================= data_global # SUBMISSION DETAILS _publ_contact_author ; Prof A. Guy Orpen, ; _publ_contact_address ; School of Chemistry, Cantocks Close, University of Bristol. Bristol. BS8 1TS. ; _publ_contact_author_phone '0117 928 7648' _publ_contact_author_fax '0117 929 0509' _publ_contact_author_email guy.orpen@bris.ac.uk _publ_requested_journal 'J.Chem,.Soc.,Dalton Trans' #======================================================================= # TITLE AND AUTHOR LIST _publ_section_title ; Pyridine adducts of Aryl bismuth (III) halides ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'James, Sian C.' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Norman, Nicholas C.' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Orpen, A. Guy' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; #======================================================================= # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the '?' in the data_? line below # by a unique identifier. data_1 #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 180 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H20 Bi I3 N4' _chemical_formula_weight 453.04 _chemical_melting_point ? _chemical_compound_source ? 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz #<--must include 'x,y,z' x,y,z -x,-y,-z _cell_length_a 9.129(2) _cell_length_b 11.301(2) _cell_length_c 13.191(2) _cell_angle_alpha 84.566(14) _cell_angle_beta 81.626(14) _cell_angle_gamma 68.692(13) _cell_volume 1253.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 180 _cell_measurement_theta_min 14.450 _cell_measurement_theta_max 336.550 _exptl_crystal_description 'block' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.402 _exptl_crystal_density_method ? _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 10.744 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.589766 _exptl_absorpt_correction_T_max 1.000000 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 13205 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5681 _reflns_number_observed 4470 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0217P)^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 'calculated' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5681 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_obs 0.0258 _refine_ls_wR_factor_all 0.0541 _refine_ls_wR_factor_obs 0.0519 _refine_ls_goodness_of_fit_all 0.878 _refine_ls_goodness_of_fit_obs 0.955 _refine_ls_restrained_S_all 0.878 _refine_ls_restrained_S_obs 0.955 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.83922(2) 0.29453(2) 0.30314(2) 0.02015(6) Uani 1 d . . I1 I 0.73183(4) 0.20786(4) 0.51663(3) 0.03277(9) Uani 1 d . . I2 I 0.81707(4) 0.54023(3) 0.37763(3) 0.03135(9) Uani 1 d . . I3 I 0.95224(4) 0.34980(4) 0.08234(3) 0.03847(11) Uani 1 d . . N1 N 1.1263(5) 0.1901(4) 0.3348(3) 0.0275(10) Uani 1 d . . N2 N 0.5540(5) 0.3874(4) 0.2586(4) 0.0298(11) Uani 1 d . . N3 N 0.8766(5) 0.0664(4) 0.2499(4) 0.0317(11) Uani 1 d . . N4 N 1.6903(8) 0.1270(7) -0.0843(6) 0.087(2) Uani 1 d . . C1 C 1.1762(6) 0.2157(5) 0.4174(5) 0.0366(14) Uani 1 d . . H1A H 1.1008(6) 0.2697(5) 0.4663(5) 0.044 Uiso 1 calc R . C2 C 1.3345(7) 0.1664(5) 0.4348(5) 0.0393(15) Uani 1 d . . H2A H 1.3669(7) 0.1857(5) 0.4945(5) 0.047 Uiso 1 calc R . C3 C 1.4424(7) 0.0890(6) 0.3631(5) 0.045(2) Uani 1 d . . H3A H 1.5515(7) 0.0553(6) 0.3722(5) 0.054 Uiso 1 calc R . C4 C 1.3927(7) 0.0606(6) 0.2786(5) 0.046(2) Uani 1 d . . H4B H 1.4659(7) 0.0058(6) 0.2292(5) 0.055 Uiso 1 calc R . C5 C 1.2328(6) 0.1135(6) 0.2667(5) 0.0393(15) Uani 1 d . . H5A H 1.1979(6) 0.0946(6) 0.2078(5) 0.047 Uiso 1 calc R . C6 C 0.5162(6) 0.3920(5) 0.1638(5) 0.0355(14) Uani 1 d . . H6A H 0.5992(6) 0.3591(5) 0.1102(5) 0.043 Uiso 1 calc R . C7 C 0.3648(7) 0.4412(6) 0.1403(5) 0.042(2) Uani 1 d . . H7A H 0.3431(7) 0.4427(6) 0.0718(5) 0.050 Uiso 1 calc R . C8 C 0.2431(6) 0.4891(6) 0.2178(5) 0.041(2) Uani 1 d . . H8A H 0.1360(6) 0.5231(6) 0.2039(5) 0.049 Uiso 1 calc R . C9 C 0.2802(7) 0.4863(6) 0.3148(5) 0.0391(15) Uani 1 d . . H9A H 0.1986(7) 0.5196(6) 0.3692(5) 0.047 Uiso 1 calc R . C10 C 0.4351(6) 0.4354(5) 0.3339(4) 0.0338(13) Uani 1 d . . H10A H 0.4593(6) 0.4340(5) 0.4018(4) 0.041 Uiso 1 calc R . C11 C 0.9214(6) -0.0350(5) 0.3144(5) 0.0352(14) Uani 1 d . . H11A H 0.9449(6) -0.0242(5) 0.3800(5) 0.042 Uiso 1 calc R . C12 C 0.9350(7) -0.1554(5) 0.2897(5) 0.0399(15) Uani 1 d . . H12A H 0.9697(7) -0.2257(5) 0.3371(5) 0.048 Uiso 1 calc R . C13 C 0.8981(7) -0.1720(6) 0.1970(5) 0.047(2) Uani 1 d . . H13A H 0.9030(7) -0.2532(6) 0.1798(5) 0.056 Uiso 1 calc R . C14 C 0.8540(9) -0.0697(6) 0.1288(6) 0.069(2) Uani 1 d . . H14A H 0.8297(9) -0.0794(6) 0.0631(6) 0.083 Uiso 1 calc R . C15 C 0.8452(8) 0.0469(6) 0.1568(5) 0.052(2) Uani 1 d . . H15A H 0.8158(8) 0.1171(6) 0.1087(5) 0.063 Uiso 1 calc R . C16 C 1.5771(10) 0.1293(7) -0.0146(5) 0.060(2) Uani 1 d . . H16A H 1.5987(10) 0.0780(7) 0.0466(5) 0.072 Uiso 1 calc R . C17 C 1.4255(10) 0.2046(8) -0.0272(6) 0.064(2) Uani 1 d . . H17A H 1.3421(10) 0.2034(8) 0.0248(6) 0.077 Uiso 1 calc R . C18 C 1.3920(7) 0.2798(6) -0.1110(6) 0.051(2) Uani 1 d . . H18A H 1.2858(7) 0.3326(6) -0.1188(6) 0.062 Uiso 1 calc R . C19 C 1.5113(9) 0.2801(6) -0.1849(5) 0.052(2) Uani 1 d . . H19A H 1.4897(9) 0.3313(6) -0.2462(5) 0.063 Uiso 1 calc R . C20 C 1.6613(9) 0.2067(9) -0.1705(6) 0.066(2) Uani 1 d . . H20A H 1.7468(9) 0.2099(9) -0.2199(6) 0.079 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 Bi1 0.01909(9) 0.02095(10) 0.02051(11) 0.00037(8) -0.00263(7) -0.00747(7) I1 0.0356(2) 0.0400(2) 0.0230(2) 0.0040(2) -0.0012(2) -0.0159(2) I2 0.0331(2) 0.0255(2) 0.0369(2) -0.0051(2) -0.0029(2) -0.0116(2) I3 0.0342(2) 0.0518(3) 0.0257(2) 0.0071(2) 0.0012(2) -0.0149(2) N1 0.025(2) 0.028(2) 0.029(3) -0.001(2) -0.001(2) -0.009(2) N2 0.023(2) 0.035(3) 0.033(3) -0.003(2) -0.004(2) -0.011(2) N3 0.032(3) 0.025(2) 0.040(3) 0.000(2) -0.012(2) -0.010(2) N4 0.055(4) 0.100(6) 0.085(6) -0.024(5) -0.027(4) 0.011(4) C1 0.034(3) 0.037(3) 0.039(4) -0.008(3) -0.006(3) -0.010(3) C2 0.040(3) 0.033(3) 0.050(4) 0.003(3) -0.026(3) -0.012(3) C3 0.023(3) 0.047(4) 0.059(5) 0.006(3) -0.010(3) -0.008(3) C4 0.031(3) 0.052(4) 0.045(4) -0.007(3) 0.003(3) -0.005(3) C5 0.031(3) 0.042(4) 0.041(4) -0.010(3) -0.004(3) -0.009(3) C6 0.029(3) 0.042(3) 0.031(3) -0.009(3) -0.004(3) -0.006(3) C7 0.039(3) 0.053(4) 0.036(4) -0.010(3) -0.010(3) -0.015(3) C8 0.022(3) 0.041(4) 0.059(5) 0.003(3) -0.009(3) -0.008(3) C9 0.029(3) 0.045(4) 0.035(4) 0.005(3) -0.002(3) -0.006(3) C10 0.029(3) 0.042(3) 0.028(3) 0.002(3) -0.002(3) -0.011(3) C11 0.040(3) 0.032(3) 0.030(3) 0.001(3) -0.002(3) -0.010(3) C12 0.043(3) 0.026(3) 0.043(4) 0.008(3) -0.001(3) -0.007(3) C13 0.052(4) 0.027(3) 0.066(5) -0.006(3) -0.024(4) -0.013(3) C14 0.109(6) 0.027(4) 0.080(6) 0.000(4) -0.070(5) -0.013(4) C15 0.077(5) 0.034(4) 0.052(5) 0.006(3) -0.043(4) -0.017(3) C16 0.070(5) 0.070(5) 0.028(4) 0.012(4) -0.011(4) -0.011(4) C17 0.079(6) 0.078(6) 0.047(5) -0.012(4) 0.012(4) -0.048(5) C18 0.031(3) 0.045(4) 0.076(6) -0.018(4) -0.012(4) -0.005(3) C19 0.073(5) 0.045(4) 0.047(5) 0.020(3) -0.024(4) -0.029(4) C20 0.048(4) 0.109(7) 0.042(5) -0.017(5) 0.011(4) -0.033(5) #======================================================================= # 10. 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 Bi1 N1 2.533(4) . ? Bi1 N2 2.563(4) . ? Bi1 N3 2.625(4) . ? Bi1 I2 2.9609(7) . ? Bi1 I3 3.0309(7) . ? Bi1 I1 3.0367(7) . ? N1 C1 1.332(7) . ? N1 C5 1.336(6) . ? N2 C6 1.336(7) . ? N2 C10 1.349(6) . ? N3 C11 1.334(7) . ? N3 C15 1.356(7) . ? N4 C16 1.273(9) . ? N4 C20 1.377(10) . ? C1 C2 1.392(7) . ? C2 C3 1.374(8) . ? C3 C4 1.369(8) . ? C4 C5 1.388(8) . ? C6 C7 1.360(8) . ? C7 C8 1.381(8) . ? C8 C9 1.366(8) . ? C9 C10 1.371(7) . ? C11 C12 1.387(8) . ? C12 C13 1.362(8) . ? C13 C14 1.370(9) . ? C14 C15 1.374(8) . ? C16 C17 1.361(10) . ? C17 C18 1.330(10) . ? C18 C19 1.353(9) . ? C19 C20 1.349(9) . ? 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 Bi1 N2 175.14(13) . . ? N1 Bi1 N3 83.35(13) . . ? N2 Bi1 N3 92.57(13) . . ? N1 Bi1 I2 92.30(10) . . ? N2 Bi1 I2 91.90(10) . . ? N3 Bi1 I2 174.71(10) . . ? N1 Bi1 I3 88.48(10) . . ? N2 Bi1 I3 88.71(11) . . ? N3 Bi1 I3 87.71(11) . . ? I2 Bi1 I3 95.21(2) . . ? N1 Bi1 I1 90.65(10) . . ? N2 Bi1 I1 91.67(11) . . ? N3 Bi1 I1 85.48(11) . . ? I2 Bi1 I1 91.56(2) . . ? I3 Bi1 I1 173.196(13) . . ? C1 N1 C5 118.4(5) . . ? C1 N1 Bi1 120.6(3) . . ? C5 N1 Bi1 120.8(4) . . ? C6 N2 C10 117.8(5) . . ? C6 N2 Bi1 123.4(3) . . ? C10 N2 Bi1 118.9(4) . . ? C11 N3 C15 116.9(5) . . ? C11 N3 Bi1 121.7(4) . . ? C15 N3 Bi1 121.4(4) . . ? C16 N4 C20 120.0(7) . . ? N1 C1 C2 122.6(5) . . ? C3 C2 C1 118.0(6) . . ? C4 C3 C2 120.0(5) . . ? C3 C4 C5 118.5(6) . . ? N1 C5 C4 122.4(6) . . ? N2 C6 C7 123.3(5) . . ? C6 C7 C8 118.8(6) . . ? C9 C8 C7 118.5(5) . . ? C8 C9 C10 120.0(5) . . ? N2 C10 C9 121.6(5) . . ? N3 C11 C12 122.7(6) . . ? C13 C12 C11 119.4(6) . . ? C12 C13 C14 119.0(6) . . ? C13 C14 C15 119.1(6) . . ? N3 C15 C14 122.9(6) . . ? N4 C16 C17 120.6(7) . . ? C18 C17 C16 121.1(7) . . ? C17 C18 C19 119.0(7) . . ? C20 C19 C18 119.1(7) . . ? C19 C20 N4 119.9(7) . . ? _refine_diff_density_max 1.005 _refine_diff_density_min -1.605 _refine_diff_density_rms 0.159 #======================================================================= data_3 #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 96 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H19 Bi Cl2 N2' _chemical_formula_weight 543.23 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6039(7) _cell_length_b 13.2094(9) _cell_length_c 15.6045(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.7770(10) _cell_angle_gamma 90.00 _cell_volume 1950.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 96 _cell_measurement_theta_min 14.450 _cell_measurement_theta_max 336.550 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.850 _exptl_crystal_density_method ? _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 9.312 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.363444 _exptl_absorpt_correction_T_max 0.491502 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 10152 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0926 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3433 _reflns_number_observed 2324 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 28 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0221P)^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 'calculated' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00040(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3405 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_obs 0.0418 _refine_ls_wR_factor_all 0.0770 _refine_ls_wR_factor_obs 0.0633 _refine_ls_goodness_of_fit_all 0.986 _refine_ls_goodness_of_fit_obs 1.017 _refine_ls_restrained_S_all 1.004 _refine_ls_restrained_S_obs 1.017 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.51636(4) 1.38189(2) 0.39621(2) 0.02334(13) Uani 1 d . . Cl1 Cl 0.7069(3) 1.2321(2) 0.4108(2) 0.0331(6) Uani 1 d . . Cl2 Cl 0.3224(3) 1.5313(2) 0.3871(2) 0.0336(6) Uani 1 d . . N1 N 0.7025(8) 1.5132(6) 0.3902(5) 0.029(2) Uani 1 d . . N2 N 0.3153(8) 1.2541(5) 0.3674(5) 0.029(2) Uani 1 d . . C1 C 0.5019(9) 1.3819(7) 0.2492(6) 0.027(2) Uani 1 d . . C2 C 0.5857(10) 1.3169(6) 0.2088(6) 0.030(2) Uani 1 d . . H2A H 0.6465(10) 1.2701(6) 0.2430(6) 0.035 Uiso 1 calc R . C3 C 0.5817(11) 1.3197(7) 0.1196(6) 0.037(3) Uani 1 d . . H3A H 0.6405(11) 1.2759(7) 0.0932(6) 0.044 Uiso 1 calc R . C4 C 0.4886(10) 1.3887(7) 0.0674(6) 0.037(2) Uani 1 d . . H4A H 0.4832(10) 1.3914(7) 0.0061(6) 0.045 Uiso 1 calc R . C5 C 0.4074(10) 1.4510(6) 0.1094(6) 0.033(3) Uani 1 d . . H5A H 0.3440(10) 1.4968(6) 0.0760(6) 0.039 Uiso 1 calc R . C6 C 0.4148(10) 1.4492(7) 0.1984(7) 0.032(3) Uani 1 d . . H6A H 0.3590(10) 1.4950(7) 0.2250(7) 0.039 Uiso 1 calc R . C7 C 0.8377(10) 1.4888(7) 0.3951(7) 0.039(3) Uani 1 d . . H7A H 0.8628(10) 1.4192(7) 0.4003(7) 0.046 Uiso 1 calc R . C8 C 0.9430(11) 1.5584(7) 0.3932(8) 0.046(3) Uani 1 d . . H8A H 1.0385(11) 1.5368(7) 0.3990(8) 0.056 Uiso 1 calc R . C9 C 0.9106(11) 1.6595(7) 0.3829(6) 0.033(3) Uani 1 d . . C10 C 0.7729(10) 1.6854(7) 0.3780(6) 0.032(2) Uani 1 d . . H10A H 0.7462(10) 1.7546(7) 0.3714(6) 0.038 Uiso 1 calc R . C11 C 0.6709(10) 1.6130(7) 0.3826(6) 0.035(2) Uani 1 d . . H11A H 0.5757(10) 1.6338(7) 0.3803(6) 0.042 Uiso 1 calc R . C12 C 1.0244(11) 1.7373(7) 0.3796(8) 0.055(3) Uani 1 d . . H12A H 1.1161(11) 1.7034(7) 0.3840(8) 0.083 Uiso 1 calc R . H12B H 1.0270(11) 1.7848(7) 0.4281(8) 0.083 Uiso 1 calc R . H12C H 1.0041(11) 1.7744(7) 0.3244(8) 0.083 Uiso 1 calc R . C13 C 0.1873(10) 1.2773(8) 0.3840(7) 0.045(3) Uani 1 d . . H13A H 0.1699(10) 1.3444(8) 0.4016(7) 0.054 Uiso 1 calc R . C14 C 0.0806(12) 1.2081(8) 0.3767(8) 0.052(3) Uani 1 d . . H14A H -0.0096(12) 1.2273(8) 0.3884(8) 0.063 Uiso 1 calc R . C15 C 0.1040(10) 1.1091(8) 0.3519(6) 0.038(3) Uani 1 d . . C16 C 0.2369(11) 1.0845(7) 0.3355(7) 0.041(3) Uani 1 d . . H16A H 0.2576(11) 1.0177(7) 0.3191(7) 0.050 Uiso 1 calc R . C17 C 0.3380(10) 1.1587(7) 0.3434(6) 0.033(2) Uani 1 d . . H17A H 0.4289(10) 1.1417(7) 0.3314(6) 0.040 Uiso 1 calc R . C18 C -0.0172(11) 1.0325(8) 0.3424(9) 0.070(4) Uani 1 d . . H18A H -0.1018(11) 1.0651(8) 0.3571(9) 0.105 Uiso 1 calc R . H18B H 0.0097(11) 0.9753(8) 0.3818(9) 0.105 Uiso 1 calc R . H18C H -0.0372(11) 1.0080(8) 0.2823(9) 0.105 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 Bi1 0.0211(2) 0.0267(2) 0.0231(2) -0.0019(2) 0.00616(13) -0.0017(2) Cl1 0.0267(14) 0.0347(14) 0.039(2) 0.0084(12) 0.0086(12) 0.0032(12) Cl2 0.0274(14) 0.0350(14) 0.040(2) -0.0085(12) 0.0102(12) 0.0018(12) N1 0.027(5) 0.032(5) 0.025(5) 0.011(4) -0.001(4) 0.011(4) N2 0.030(5) 0.023(4) 0.035(6) 0.002(4) 0.010(4) 0.006(4) C1 0.023(5) 0.025(5) 0.029(5) 0.002(5) -0.002(4) -0.004(5) C2 0.038(6) 0.022(5) 0.031(6) 0.003(4) 0.011(5) 0.005(5) C3 0.040(7) 0.042(6) 0.034(7) -0.015(5) 0.023(6) -0.015(6) C4 0.056(7) 0.025(5) 0.030(6) 0.002(5) 0.004(5) -0.005(6) C5 0.042(6) 0.021(5) 0.032(7) 0.010(5) -0.002(5) 0.013(5) C6 0.033(6) 0.031(6) 0.035(7) -0.007(5) 0.011(5) 0.004(5) C7 0.020(6) 0.023(5) 0.071(9) 0.011(5) 0.001(6) 0.003(5) C8 0.019(6) 0.039(7) 0.079(9) 0.004(6) 0.001(6) -0.002(5) C9 0.032(6) 0.028(5) 0.038(7) 0.004(5) 0.001(5) -0.012(5) C10 0.028(6) 0.027(6) 0.041(7) -0.003(5) 0.007(5) -0.006(5) C11 0.035(6) 0.037(6) 0.031(6) -0.004(6) 0.003(5) 0.005(6) C12 0.045(7) 0.045(6) 0.075(10) 0.001(7) 0.005(7) -0.014(7) C13 0.032(6) 0.047(7) 0.064(9) -0.002(6) 0.032(6) -0.001(6) C14 0.035(7) 0.042(7) 0.085(10) -0.017(6) 0.022(7) -0.016(6) C15 0.032(6) 0.039(6) 0.045(7) 0.002(6) 0.010(5) -0.011(6) C16 0.041(7) 0.033(6) 0.049(8) -0.004(5) 0.006(6) -0.003(5) C17 0.021(5) 0.036(6) 0.043(7) -0.006(5) 0.008(5) 0.009(5) C18 0.051(9) 0.040(7) 0.117(13) -0.017(7) 0.007(8) -0.019(6) #======================================================================= # 10. 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 Bi1 C1 2.275(9) . ? Bi1 N1 2.504(8) . ? Bi1 N2 2.547(8) . ? Bi1 Cl1 2.678(2) . ? Bi1 Cl2 2.701(2) . ? Bi1 Cl2 3.657(3) 3_686 ? Cl2 Bi1 3.657(3) 3_686 ? N1 C7 1.327(11) . ? N1 C11 1.353(11) . ? N2 C13 1.335(11) . ? N2 C17 1.343(10) . ? C1 C6 1.375(12) . ? C1 C2 1.398(11) . ? C2 C3 1.386(12) . ? C3 C4 1.431(13) . ? C4 C5 1.374(12) . ? C5 C6 1.378(12) . ? C7 C8 1.372(12) . ? C8 C9 1.374(12) . ? C9 C10 1.355(12) . ? C9 C12 1.508(12) . ? C10 C11 1.380(12) . ? C13 C14 1.364(13) . ? C14 C15 1.392(13) . ? C15 C16 1.382(12) . ? C15 C18 1.530(12) . ? C16 C17 1.371(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 C1 Bi1 N1 83.3(3) . . ? C1 Bi1 N2 84.7(3) . . ? N1 Bi1 N2 167.8(2) . . ? C1 Bi1 Cl1 90.6(2) . . ? N1 Bi1 Cl1 91.9(2) . . ? N2 Bi1 Cl1 90.7(2) . . ? C1 Bi1 Cl2 91.3(2) . . ? N1 Bi1 Cl2 89.0(2) . . ? N2 Bi1 Cl2 88.8(2) . . ? Cl1 Bi1 Cl2 178.01(7) . . ? C1 Bi1 Cl2 151.2(2) . 3_686 ? N1 Bi1 Cl2 67.9(2) . 3_686 ? N2 Bi1 Cl2 124.1(2) . 3_686 ? Cl1 Bi1 Cl2 88.69(7) . 3_686 ? Cl2 Bi1 Cl2 89.98(7) . 3_686 ? Bi1 Cl2 Bi1 90.02(7) . 3_686 ? C7 N1 C11 116.4(8) . . ? C7 N1 Bi1 121.8(6) . . ? C11 N1 Bi1 121.8(6) . . ? C13 N2 C17 117.9(9) . . ? C13 N2 Bi1 120.6(6) . . ? C17 N2 Bi1 121.1(6) . . ? C6 C1 C2 118.5(9) . . ? C6 C1 Bi1 120.6(7) . . ? C2 C1 Bi1 120.9(7) . . ? C3 C2 C1 121.1(9) . . ? C2 C3 C4 119.8(9) . . ? C5 C4 C3 117.3(9) . . ? C4 C5 C6 122.3(9) . . ? C1 C6 C5 120.9(9) . . ? N1 C7 C8 123.6(9) . . ? C7 C8 C9 120.1(10) . . ? C10 C9 C8 116.8(9) . . ? C10 C9 C12 122.1(9) . . ? C8 C9 C12 121.0(10) . . ? C9 C10 C11 121.1(9) . . ? N1 C11 C10 121.9(9) . . ? N2 C13 C14 122.2(9) . . ? C13 C14 C15 119.9(10) . . ? C16 C15 C14 118.0(9) . . ? C16 C15 C18 122.6(9) . . ? C14 C15 C18 119.4(9) . . ? C17 C16 C15 118.6(9) . . ? N2 C17 C16 123.3(9) . . ? _refine_diff_density_max 0.800 _refine_diff_density_min -0.992 _refine_diff_density_rms 0.197 #======================================================================= data_4 #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 135 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. The crystal was a non-merohedral twin with twin law (1 0 0, 0 -1 0, 0 0 1/3). Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H19 Bi Br2 N2' _chemical_formula_weight 632.15 _chemical_melting_point ? _chemical_compound_source ? 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.812(3) _cell_length_b 13.392(5) _cell_length_c 15.845(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.15(3) _cell_angle_gamma 90.00 _cell_volume 2035.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 135 _cell_measurement_theta_min 14.552 _cell_measurement_theta_max 336.550 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.063 _exptl_crystal_density_method ? _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 12.589 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.162139 _exptl_absorpt_correction_T_max 0.261711 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 10441 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1313 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10441 _reflns_number_observed 6531 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 66 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0490P)^2^+10.3824P] 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 'calculated' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00042(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 10375 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1236 _refine_ls_R_factor_obs 0.0646 _refine_ls_wR_factor_all 0.1555 _refine_ls_wR_factor_obs 0.1233 _refine_ls_goodness_of_fit_all 1.028 _refine_ls_goodness_of_fit_obs 1.043 _refine_ls_restrained_S_all 1.040 _refine_ls_restrained_S_obs 1.043 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi -0.47809(5) 0.62010(3) 0.39270(3) 0.0255(2) Uani 1 d . . Br1 Br -0.27525(13) 0.77458(9) 0.41605(9) 0.0350(3) Uani 1 d . . Br2 Br -0.68503(13) 0.46932(9) 0.38302(9) 0.0376(4) Uani 1 d . . N1 N -0.2983(9) 0.4869(6) 0.3889(6) 0.026(2) Uani 1 d . . N2 N -0.6741(10) 0.7503(7) 0.3678(7) 0.031(3) Uani 1 d . . C1 C -0.4971(11) 0.6185(8) 0.2479(8) 0.026(3) Uani 1 d . . C2 C -0.5855(13) 0.5554(8) 0.1965(9) 0.035(3) Uani 1 d . . H2A H -0.6422(13) 0.5117(8) 0.2216(9) 0.042 Uiso 1 calc R . C3 C -0.5951(12) 0.5532(8) 0.1068(8) 0.029(3) Uani 1 d . . H3A H -0.6589(12) 0.5092(8) 0.0716(8) 0.034 Uiso 1 calc R . C4 C -0.5098(14) 0.6162(9) 0.0694(8) 0.040(3) Uani 1 d . . H4A H -0.5131(14) 0.6131(9) 0.0091(8) 0.048 Uiso 1 calc R . C5 C -0.4221(13) 0.6820(9) 0.1198(8) 0.037(3) Uani 1 d . . H5A H -0.3683(13) 0.7274(9) 0.0943(8) 0.045 Uiso 1 calc R . C6 C -0.4120(14) 0.6824(8) 0.2079(9) 0.038(3) Uani 1 d . . H6A H -0.3472(14) 0.7260(8) 0.2428(9) 0.045 Uiso 1 calc R . C7 C -0.1674(15) 0.5122(9) 0.3920(11) 0.065(5) Uani 1 d . . H7A H -0.1410(15) 0.5805(9) 0.3983(11) 0.078 Uiso 1 calc R . C8 C -0.0690(15) 0.4415(10) 0.3862(11) 0.061(5) Uani 1 d . . H8A H 0.0246(15) 0.4614(10) 0.3883(11) 0.073 Uiso 1 calc R . C9 C -0.1038(15) 0.3423(10) 0.3775(9) 0.045(4) Uani 1 d . . C10 C -0.2340(14) 0.3169(9) 0.3787(9) 0.041(4) Uani 1 d . . H10A H -0.2593(14) 0.2484(9) 0.3778(9) 0.050 Uiso 1 calc R . C11 C -0.3328(15) 0.3893(9) 0.3812(9) 0.045(4) Uani 1 d . . H11A H -0.4271(15) 0.3702(9) 0.3775(9) 0.054 Uiso 1 calc R . C12 C 0.0064(14) 0.2607(9) 0.3698(10) 0.058(5) Uani 1 d . . H12A H 0.0963(14) 0.2926(9) 0.3699(10) 0.087 Uiso 1 calc R . H12B H -0.0243(14) 0.2235(9) 0.3158(10) 0.087 Uiso 1 calc R . H12C H 0.0163(14) 0.2147(9) 0.4188(10) 0.087 Uiso 1 calc R . C13 C -0.7904(13) 0.7330(8) 0.3907(9) 0.037(3) Uani 1 d . . H13A H -0.8060(13) 0.6687(8) 0.4123(9) 0.044 Uiso 1 calc R . C14 C -0.8930(14) 0.8046(10) 0.3850(10) 0.056(4) Uani 1 d . . H14A H -0.9799(14) 0.7882(10) 0.3989(10) 0.067 Uiso 1 calc R . C15 C -0.8687(15) 0.9004(9) 0.3590(10) 0.048(4) Uani 1 d . . C16 C -0.7409(13) 0.9178(9) 0.3381(8) 0.036(3) Uani 1 d . . H16A H -0.7174(13) 0.9831(9) 0.3225(8) 0.043 Uiso 1 calc R . C17 C -0.6499(15) 0.8425(8) 0.3400(8) 0.040(4) Uani 1 d . . H17A H -0.5657(15) 0.8546(8) 0.3212(8) 0.048 Uiso 1 calc R . C18 C -0.9802(18) 0.9797(11) 0.3557(13) 0.100(7) Uani 1 d . . H18A H -1.0615(18) 0.9503(11) 0.3731(13) 0.150 Uiso 1 calc R . H18B H -1.0077(18) 1.0057(11) 0.2968(13) 0.150 Uiso 1 calc R . H18C H -0.9433(18) 1.0343(11) 0.3951(13) 0.150 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 Bi1 0.0248(3) 0.0240(2) 0.0285(3) 0.0018(3) 0.0077(2) 0.0016(2) Br1 0.0313(8) 0.0323(7) 0.0420(9) -0.0070(6) 0.0086(7) -0.0038(6) Br2 0.0308(8) 0.0333(7) 0.0507(10) 0.0085(7) 0.0133(7) -0.0024(6) N1 0.012(5) 0.027(6) 0.034(7) 0.003(5) -0.003(5) 0.000(5) N2 0.023(6) 0.031(6) 0.036(7) 0.013(5) 0.000(5) -0.001(5) C1 0.024(6) 0.015(5) 0.042(7) 0.007(6) 0.016(6) 0.001(5) C2 0.046(9) 0.021(7) 0.039(9) 0.000(6) 0.011(7) 0.000(6) C3 0.029(7) 0.015(6) 0.037(8) -0.002(6) -0.004(6) 0.000(5) C4 0.060(9) 0.036(7) 0.025(7) -0.002(7) 0.009(7) 0.027(8) C5 0.052(9) 0.040(8) 0.018(8) 0.002(6) 0.006(7) -0.008(7) C6 0.048(9) 0.026(7) 0.043(9) 0.006(6) 0.019(7) 0.004(6) C7 0.046(10) 0.019(7) 0.125(17) -0.013(9) 0.006(10) -0.003(7) C8 0.027(9) 0.046(9) 0.105(15) -0.020(9) 0.005(9) 0.006(7) C9 0.051(10) 0.040(8) 0.037(9) 0.007(7) -0.004(8) 0.020(7) C10 0.038(9) 0.026(7) 0.060(11) 0.006(7) 0.009(8) -0.006(7) C11 0.049(9) 0.029(7) 0.061(10) 0.001(8) 0.021(8) -0.002(7) C12 0.045(10) 0.054(8) 0.070(12) -0.007(8) 0.001(9) 0.032(8) C13 0.034(8) 0.030(7) 0.055(9) -0.004(7) 0.028(8) -0.010(6) C14 0.025(8) 0.050(9) 0.091(14) 0.013(9) 0.008(8) 0.021(7) C15 0.049(10) 0.045(9) 0.059(10) -0.003(8) 0.031(8) 0.015(7) C16 0.040(9) 0.026(7) 0.042(9) -0.008(6) 0.010(7) 0.000(6) C17 0.054(10) 0.031(7) 0.032(8) -0.002(6) 0.005(7) -0.019(7) C18 0.109(15) 0.066(11) 0.135(19) 0.032(12) 0.048(14) 0.074(11) #======================================================================= # 10. 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 Bi1 C1 2.263(12) . ? Bi1 N1 2.519(9) . ? Bi1 N2 2.564(9) . ? Bi1 Br1 2.8403(15) . ? Bi1 Br2 2.8448(15) . ? Bi1 Br2 3.772(2) 3_466 ? Br2 Bi1 3.772(2) 3_466 ? N1 C7 1.319(15) . ? N1 C11 1.349(13) . ? N2 C13 1.290(13) . ? N2 C17 1.348(13) . ? C1 C2 1.35(2) . ? C1 C6 1.434(14) . ? C2 C3 1.40(2) . ? C3 C4 1.40(2) . ? C4 C5 1.37(2) . ? C5 C6 1.38(2) . ? C7 C8 1.37(2) . ? C8 C9 1.37(2) . ? C9 C10 1.33(2) . ? C9 C12 1.56(2) . ? C10 C11 1.38(2) . ? C13 C14 1.38(2) . ? C14 C15 1.38(2) . ? C15 C16 1.38(2) . ? C15 C18 1.52(2) . ? C16 C17 1.34(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 C1 Bi1 N1 83.0(3) . . ? C1 Bi1 N2 87.2(4) . . ? N1 Bi1 N2 169.9(3) . . ? C1 Bi1 Br1 92.6(3) . . ? N1 Bi1 Br1 92.5(2) . . ? N2 Bi1 Br1 90.4(2) . . ? C1 Bi1 Br2 91.9(3) . . ? N1 Bi1 Br2 89.5(2) . . ? N2 Bi1 Br2 88.3(2) . . ? Br1 Bi1 Br2 175.29(4) . . ? C1 Bi1 Br2 151.7(3) . 3_466 ? N1 Bi1 Br2 68.7(2) . 3_466 ? N2 Bi1 Br2 121.1(2) . 3_466 ? Br1 Bi1 Br2 87.81(4) . 3_466 ? Br2 Bi1 Br2 88.97(4) . 3_466 ? Bi1 Br2 Bi1 91.03(4) . 3_466 ? C7 N1 C11 118.5(10) . . ? C7 N1 Bi1 119.9(8) . . ? C11 N1 Bi1 121.6(8) . . ? C13 N2 C17 118.9(11) . . ? C13 N2 Bi1 120.9(8) . . ? C17 N2 Bi1 119.7(9) . . ? C2 C1 C6 117.8(11) . . ? C2 C1 Bi1 121.4(8) . . ? C6 C1 Bi1 120.8(9) . . ? C1 C2 C3 121.3(11) . . ? C2 C3 C4 119.7(11) . . ? C5 C4 C3 119.9(12) . . ? C4 C5 C6 119.9(12) . . ? C5 C6 C1 121.4(13) . . ? N1 C7 C8 121.0(12) . . ? C7 C8 C9 120.8(13) . . ? C10 C9 C8 117.8(12) . . ? C10 C9 C12 120.5(12) . . ? C8 C9 C12 121.6(13) . . ? C9 C10 C11 120.5(12) . . ? N1 C11 C10 121.3(12) . . ? N2 C13 C14 122.2(12) . . ? C13 C14 C15 119.7(12) . . ? C16 C15 C14 116.7(12) . . ? C16 C15 C18 123.9(13) . . ? C14 C15 C18 119.4(13) . . ? C17 C16 C15 120.0(12) . . ? C16 C17 N2 122.3(12) . . ? _refine_diff_density_max 1.407 _refine_diff_density_min -1.026 _refine_diff_density_rms 0.244 #======================================================================= data_5 #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 95 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H31 Bi Br2 N2' _chemical_formula_weight 716.31 _chemical_melting_point ? _chemical_compound_source ? 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _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 9.828(2) _cell_length_b 11.673(2) _cell_length_c 12.475(3) _cell_angle_alpha 101.65(3) _cell_angle_beta 101.75(3) _cell_angle_gamma 108.01(3) _cell_volume 1277.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 95 _cell_measurement_theta_min 14.454 _cell_measurement_theta_max 336.550 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.862 _exptl_crystal_density_method ? _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 10.041 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.055826 _exptl_absorpt_correction_T_max 0.094962 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 13086 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5769 _reflns_number_observed 4713 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0246P)^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 'calculated' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5769 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_obs 0.0371 _refine_ls_wR_factor_all 0.0680 _refine_ls_wR_factor_obs 0.0647 _refine_ls_goodness_of_fit_all 1.057 _refine_ls_goodness_of_fit_obs 1.118 _refine_ls_restrained_S_all 1.057 _refine_ls_restrained_S_obs 1.118 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.18970(2) 0.11197(2) 0.20198(2) 0.02274(6) Uani 1 d . . Br1 Br 0.17234(7) 0.21722(5) 0.42654(5) 0.03357(14) Uani 1 d . . Br2 Br 0.20045(7) 0.01677(5) -0.02004(5) 0.03416(14) Uani 1 d . . C1 C 0.4233(6) 0.1190(4) 0.2770(4) 0.0248(11) Uani 1 d . . C2 C 0.4714(6) 0.1208(5) 0.3894(5) 0.0305(13) Uani 1 d . . H2A H 0.4050(6) 0.1164(5) 0.4355(5) 0.037 Uiso 1 calc R . C3 C 0.6167(7) 0.1290(6) 0.4358(5) 0.040(2) Uani 1 d . . H3A H 0.6489(7) 0.1318(6) 0.5137(5) 0.048 Uiso 1 calc R . C4 C 0.7126(7) 0.1332(5) 0.3714(5) 0.0373(15) Uani 1 d . . H4A H 0.8111(7) 0.1379(5) 0.4037(5) 0.045 Uiso 1 calc R . C5 C 0.6658(6) 0.1305(5) 0.2577(5) 0.0326(13) Uani 1 d . . H5A H 0.7329(6) 0.1340(5) 0.2123(5) 0.039 Uiso 1 calc R . C6 C 0.5214(6) 0.1228(5) 0.2103(5) 0.0303(13) Uani 1 d . . H6A H 0.4896(6) 0.1201(5) 0.1323(5) 0.036 Uiso 1 calc R . N1 N 0.0996(5) -0.1091(4) 0.2228(4) 0.0273(10) Uani 1 d . . C7 C 0.0796(6) -0.2096(5) 0.1396(5) 0.0313(13) Uani 1 d . . H7A H 0.0965(6) -0.1978(5) 0.0696(5) 0.038 Uiso 1 calc R . C8 C 0.0359(6) -0.3296(5) 0.1501(5) 0.0299(13) Uani 1 d . . H8A H 0.0219(6) -0.3981(5) 0.0877(5) 0.036 Uiso 1 calc R . C9 C 0.0120(6) -0.3512(5) 0.2515(4) 0.0248(11) Uani 1 d . . C10 C 0.0310(6) -0.2459(5) 0.3364(5) 0.0277(12) Uani 1 d . . H10A H 0.0142(6) -0.2553(5) 0.4070(5) 0.033 Uiso 1 calc R . C11 C 0.0738(6) -0.1276(5) 0.3208(5) 0.0292(13) Uani 1 d . . H11A H 0.0853(6) -0.0576(5) 0.3808(5) 0.035 Uiso 1 calc R . C12 C -0.0310(6) -0.4804(5) 0.2730(5) 0.0298(13) Uani 1 d . . C13 C 0.0894(8) -0.4739(6) 0.3765(5) 0.047(2) Uani 1 d . . H13A H 0.1863(8) -0.4513(6) 0.3604(5) 0.070 Uiso 1 calc R . H13B H 0.0642(8) -0.5560(6) 0.3916(5) 0.070 Uiso 1 calc R . H13C H 0.0946(8) -0.4104(6) 0.4435(5) 0.070 Uiso 1 calc R . C14 C -0.1841(7) -0.5156(5) 0.2949(6) 0.042(2) Uani 1 d . . H14A H -0.2115(7) -0.5983(5) 0.3086(6) 0.063 Uiso 1 calc R . H14B H -0.2587(7) -0.5181(5) 0.2281(6) 0.063 Uiso 1 calc R . H14C H -0.1803(7) -0.4528(5) 0.3619(6) 0.063 Uiso 1 calc R . C15 C -0.0389(8) -0.5834(5) 0.1713(5) 0.045(2) Uani 1 d . . H15A H 0.0584(8) -0.5627(5) 0.1558(5) 0.067 Uiso 1 calc R . H15B H -0.1150(8) -0.5893(5) 0.1038(5) 0.067 Uiso 1 calc R . H15C H -0.0650(8) -0.6641(5) 0.1891(5) 0.067 Uiso 1 calc R . N2 N 0.3268(5) 0.3308(4) 0.1938(4) 0.0292(11) Uani 1 d . . C16 C 0.2963(6) 0.3621(5) 0.0963(5) 0.0298(13) Uani 1 d . . H16A H 0.2340(6) 0.2978(5) 0.0284(5) 0.036 Uiso 1 calc R . C17 C 0.3523(6) 0.4846(5) 0.0910(5) 0.0291(13) Uani 1 d . . H17A H 0.3283(6) 0.5023(5) 0.0199(5) 0.035 Uiso 1 calc R . C18 C 0.4431(6) 0.5823(5) 0.1882(5) 0.0257(12) Uani 1 d . . C19 C 0.4757(6) 0.5451(5) 0.2881(5) 0.0292(12) Uani 1 d . . H19A H 0.5408(6) 0.6062(5) 0.3569(5) 0.035 Uiso 1 calc R . C20 C 0.4151(6) 0.4229(5) 0.2875(5) 0.0305(13) Uani 1 d . . H20A H 0.4370(6) 0.4023(5) 0.3573(5) 0.037 Uiso 1 calc R . C21 C 0.5061(6) 0.7183(5) 0.1897(4) 0.0261(12) Uani 1 d . . C22 C 0.4485(7) 0.7403(5) 0.0752(5) 0.0364(14) Uani 1 d . . H22A H 0.4928(7) 0.8298(5) 0.0810(5) 0.055 Uiso 1 calc R . H22B H 0.3396(7) 0.7142(5) 0.0552(5) 0.055 Uiso 1 calc R . H22C H 0.4764(7) 0.6911(5) 0.0159(5) 0.055 Uiso 1 calc R . C23 C 0.4602(7) 0.7961(5) 0.2803(5) 0.0381(15) Uani 1 d . . H23A H 0.5001(7) 0.8848(5) 0.2826(5) 0.057 Uiso 1 calc R . H23B H 0.5002(7) 0.7864(5) 0.3552(5) 0.057 Uiso 1 calc R . H23C H 0.3511(7) 0.7666(5) 0.2611(5) 0.057 Uiso 1 calc R . C24 C 0.6763(6) 0.7635(5) 0.2222(5) 0.0355(14) Uani 1 d . . H24A H 0.7172(6) 0.8518(5) 0.2232(5) 0.053 Uiso 1 calc R . H24B H 0.7067(6) 0.7125(5) 0.1662(5) 0.053 Uiso 1 calc R . H24C H 0.7142(6) 0.7552(5) 0.2982(5) 0.053 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 Bi1 0.02389(11) 0.02249(10) 0.02275(10) 0.00715(7) 0.00792(8) 0.00844(7) Br1 0.0393(4) 0.0358(3) 0.0311(3) 0.0077(2) 0.0170(3) 0.0179(3) Br2 0.0352(3) 0.0385(3) 0.0247(3) 0.0062(2) 0.0107(3) 0.0084(3) C1 0.022(3) 0.025(3) 0.030(3) 0.007(2) 0.010(2) 0.011(2) C2 0.027(3) 0.041(3) 0.029(3) 0.009(2) 0.013(3) 0.017(3) C3 0.036(4) 0.053(4) 0.030(3) 0.006(3) 0.006(3) 0.020(3) C4 0.028(3) 0.033(3) 0.045(4) 0.004(3) 0.005(3) 0.011(3) C5 0.033(3) 0.028(3) 0.039(3) 0.005(2) 0.022(3) 0.009(2) C6 0.032(3) 0.029(3) 0.030(3) 0.009(2) 0.011(3) 0.007(2) N1 0.023(2) 0.028(2) 0.031(2) 0.011(2) 0.007(2) 0.009(2) C7 0.037(3) 0.033(3) 0.026(3) 0.012(2) 0.012(3) 0.011(3) C8 0.036(3) 0.029(3) 0.030(3) 0.010(2) 0.016(3) 0.014(2) C9 0.018(3) 0.026(3) 0.030(3) 0.008(2) 0.010(2) 0.005(2) C10 0.029(3) 0.032(3) 0.025(3) 0.010(2) 0.011(2) 0.012(2) C11 0.027(3) 0.028(3) 0.028(3) 0.005(2) 0.006(3) 0.007(2) C12 0.035(3) 0.024(3) 0.033(3) 0.008(2) 0.012(3) 0.012(2) C13 0.056(5) 0.050(4) 0.048(4) 0.027(3) 0.017(3) 0.028(3) C14 0.046(4) 0.027(3) 0.060(4) 0.015(3) 0.030(3) 0.010(3) C15 0.062(5) 0.032(3) 0.053(4) 0.013(3) 0.034(4) 0.024(3) N2 0.029(3) 0.024(2) 0.035(3) 0.009(2) 0.010(2) 0.011(2) C16 0.036(3) 0.026(3) 0.028(3) 0.007(2) 0.009(3) 0.012(2) C17 0.035(3) 0.029(3) 0.028(3) 0.010(2) 0.010(3) 0.016(2) C18 0.022(3) 0.030(3) 0.032(3) 0.011(2) 0.014(2) 0.012(2) C19 0.024(3) 0.030(3) 0.028(3) 0.007(2) 0.006(2) 0.004(2) C20 0.033(3) 0.031(3) 0.026(3) 0.011(2) 0.008(3) 0.009(2) C21 0.026(3) 0.025(3) 0.028(3) 0.010(2) 0.008(2) 0.009(2) C22 0.041(4) 0.033(3) 0.038(3) 0.018(3) 0.009(3) 0.012(3) C23 0.040(4) 0.027(3) 0.045(4) 0.006(3) 0.013(3) 0.010(3) C24 0.032(3) 0.039(3) 0.041(3) 0.020(3) 0.016(3) 0.012(3) #======================================================================= # 10. 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 Bi1 C1 2.265(5) . ? Bi1 N2 2.527(4) . ? Bi1 N1 2.542(4) . ? Bi1 Br2 2.8047(10) . ? Bi1 Br1 2.8846(10) . ? Bi1 Br2 3.691(2) 2 ? Br2 Bi1 3.691(2) 2 ? C1 C2 1.380(7) . ? C1 C6 1.392(8) . ? C2 C3 1.392(8) . ? C3 C4 1.354(8) . ? C4 C5 1.389(8) . ? C5 C6 1.389(8) . ? N1 C7 1.332(6) . ? N1 C11 1.344(7) . ? C7 C8 1.374(7) . ? C8 C9 1.391(7) . ? C9 C10 1.386(7) . ? C9 C12 1.530(7) . ? C10 C11 1.380(7) . ? C12 C14 1.528(8) . ? C12 C15 1.532(7) . ? C12 C13 1.534(8) . ? N2 C20 1.334(7) . ? N2 C16 1.341(6) . ? C16 C17 1.386(7) . ? C17 C18 1.393(7) . ? C18 C19 1.408(7) . ? C18 C21 1.511(7) . ? C19 C20 1.364(7) . ? C21 C24 1.528(8) . ? C21 C22 1.528(7) . ? C21 C23 1.533(8) . ? 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 C1 Bi1 N2 83.3(2) . . ? C1 Bi1 N1 86.2(2) . . ? N2 Bi1 N1 169.46(14) . . ? C1 Bi1 Br2 91.10(14) . . ? N2 Bi1 Br2 88.91(11) . . ? N1 Bi1 Br2 90.44(11) . . ? C1 Bi1 Br1 90.83(14) . . ? N2 Bi1 Br1 89.59(11) . . ? N1 Bi1 Br1 91.42(11) . . ? Br2 Bi1 Br1 177.40(2) . . ? C1 Bi1 Br2 158.36(12) . 2 ? N2 Bi1 Br2 111.60(11) . 2 ? N1 Bi1 Br2 78.29(10) . 2 ? Br2 Bi1 Br2 74.20(4) . 2 ? Br1 Bi1 Br2 104.42(4) . 2 ? Bi1 Br2 Bi1 105.80(4) . 2 ? C2 C1 C6 118.9(5) . . ? C2 C1 Bi1 120.7(4) . . ? C6 C1 Bi1 120.3(4) . . ? C1 C2 C3 120.4(6) . . ? C4 C3 C2 120.9(6) . . ? C3 C4 C5 119.5(6) . . ? C6 C5 C4 120.3(6) . . ? C5 C6 C1 120.0(5) . . ? C7 N1 C11 117.6(5) . . ? C7 N1 Bi1 122.1(4) . . ? C11 N1 Bi1 120.3(3) . . ? N1 C7 C8 123.2(5) . . ? C7 C8 C9 120.4(5) . . ? C10 C9 C8 115.5(5) . . ? C10 C9 C12 120.1(5) . . ? C8 C9 C12 124.3(5) . . ? C11 C10 C9 121.5(5) . . ? N1 C11 C10 121.6(5) . . ? C14 C12 C9 109.6(4) . . ? C14 C12 C15 108.1(5) . . ? C9 C12 C15 112.2(5) . . ? C14 C12 C13 111.1(5) . . ? C9 C12 C13 108.1(4) . . ? C15 C12 C13 107.8(5) . . ? C20 N2 C16 117.5(5) . . ? C20 N2 Bi1 121.8(4) . . ? C16 N2 Bi1 120.1(3) . . ? N2 C16 C17 122.4(5) . . ? C16 C17 C18 121.0(5) . . ? C17 C18 C19 114.8(5) . . ? C17 C18 C21 124.1(5) . . ? C19 C18 C21 121.1(5) . . ? C20 C19 C18 121.1(5) . . ? N2 C20 C19 123.2(5) . . ? C18 C21 C24 109.4(4) . . ? C18 C21 C22 112.9(4) . . ? C24 C21 C22 109.2(5) . . ? C18 C21 C23 108.2(5) . . ? C24 C21 C23 108.8(4) . . ? C22 C21 C23 108.2(4) . . ? _refine_diff_density_max 1.722 _refine_diff_density_min -1.436 _refine_diff_density_rms 0.157 #======================================================================= data_7 # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 85 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H15 Bi Br2 N2' _chemical_formula_weight 604.10 _chemical_melting_point ? _chemical_compound_source ? 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C2/c' loop_ _symmetry_equiv_pos_as_xyz '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, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.520(3) _cell_length_b 14.687(2) _cell_length_c 8.699(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.60(1) _cell_angle_gamma 90.00 _cell_volume 1703.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 85 _cell_measurement_theta_min 15.104 _cell_measurement_theta_max 335.919 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.356 _exptl_crystal_density_method ? _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 15.039 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.512433 _exptl_absorpt_correction_T_max 1.000000 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 8717 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1949 _reflns_number_observed 1645 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0425P)^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 'calculated' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00038(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1949 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_obs 0.0340 _refine_ls_wR_factor_all 0.0787 _refine_ls_wR_factor_obs 0.0755 _refine_ls_goodness_of_fit_all 1.023 _refine_ls_goodness_of_fit_obs 1.074 _refine_ls_restrained_S_all 1.023 _refine_ls_restrained_S_obs 1.074 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.5000 0.39069(2) -0.7500 0.01759(13) Uani 1 d S . Br1 Br 0.59991(5) 0.38617(4) -0.43527(7) 0.0269(2) Uani 1 d . . N1 N 0.3312(4) 0.3719(3) -0.6604(6) 0.0211(11) Uani 1 d . . C1 C 0.5000 0.2353(5) -0.7500 0.017(2) Uani 1 d S . C2 C 0.5784(4) 0.1875(4) -0.6608(7) 0.0220(13) Uani 1 d . . H2A H 0.6319(4) 0.2195(4) -0.5990(7) 0.026 Uiso 1 calc R . C3 C 0.5781(5) 0.0929(4) -0.6626(8) 0.0285(15) Uani 1 d . . H3A H 0.6322(5) 0.0606(4) -0.6030(8) 0.034 Uiso 1 calc R . C4 C 0.5000 0.0450(6) -0.7500 0.031(2) Uani 1 d S . H4 H 0.5000 -0.0197(6) -0.7500 0.037 Uiso 1 calc SR . C5 C 0.2462(5) 0.3515(4) -0.7574(8) 0.0256(13) Uani 1 d . . H5A H 0.2487(5) 0.3449(4) -0.8653(8) 0.031 Uiso 1 calc R . C6 C 0.1564(5) 0.3398(5) -0.7089(8) 0.0280(15) Uani 1 d . . H6A H 0.0985(5) 0.3243(5) -0.7819(8) 0.034 Uiso 1 calc R . C7 C 0.1498(5) 0.3504(5) -0.5545(8) 0.0276(15) Uani 1 d . . H7A H 0.0877(5) 0.3426(5) -0.5184(8) 0.033 Uiso 1 calc R . C8 C 0.2361(5) 0.3729(5) -0.4530(8) 0.029(2) Uani 1 d . . H8A H 0.2343(5) 0.3816(5) -0.3453(8) 0.035 Uiso 1 calc R . C9 C 0.3251(5) 0.3825(4) -0.5093(8) 0.0270(14) Uani 1 d . . H9A H 0.3842(5) 0.3972(4) -0.4383(8) 0.032 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 Bi1 0.0168(2) 0.0177(2) 0.0158(2) 0.000 -0.00437(11) 0.000 Br1 0.0277(3) 0.0312(4) 0.0182(3) -0.0026(2) -0.0067(3) 0.0021(3) N1 0.016(3) 0.024(3) 0.022(3) -0.003(2) 0.000(2) 0.000(2) C1 0.018(4) 0.015(4) 0.020(4) 0.000 0.005(3) 0.000 C2 0.014(3) 0.027(3) 0.022(3) 0.002(3) -0.004(2) 0.001(2) C3 0.020(3) 0.029(4) 0.034(4) 0.005(3) -0.002(3) 0.006(3) C4 0.030(5) 0.021(4) 0.039(6) 0.000 -0.005(4) 0.000 C5 0.020(3) 0.033(4) 0.022(3) -0.005(3) 0.000(3) 0.008(3) C6 0.017(3) 0.031(4) 0.032(4) -0.002(3) -0.006(3) 0.003(3) C7 0.019(3) 0.034(4) 0.030(4) 0.003(3) 0.004(3) 0.002(3) C8 0.026(4) 0.037(4) 0.025(4) 0.004(3) 0.007(3) 0.000(3) C9 0.027(3) 0.029(4) 0.024(3) 0.003(3) 0.000(3) -0.002(3) #======================================================================= # 10. MOLECULAR GEOMETRY ; 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 Bi1 C1 2.282(8) . ? Bi1 N1 2.547(5) . ? Bi1 N1 2.547(5) 2_653 ? Bi1 Br1 2.8444(6) 2_653 ? Bi1 Br1 2.8445(6) . ? Bi1 Br1 3.9861(7) 5_664 ? Bi1 Br1 3.9861(7) 6_565 ? N1 C9 1.340(8) . ? N1 C5 1.341(8) . ? C1 C2 1.394(7) . ? C1 C2 1.394(7) 2_653 ? C2 C3 1.389(9) . ? C3 C4 1.386(8) . ? C4 C3 1.386(8) 2_653 ? C5 C6 1.361(9) . ? C6 C7 1.369(9) . ? C7 C8 1.381(10) . ? C8 C9 1.379(9) . ? 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 C1 Bi1 N1 83.79(11) . . ? C1 Bi1 N1 83.79(11) . 2_653 ? N1 Bi1 N1 167.6(2) . 2_653 ? C1 Bi1 Br1 88.659(15) . 2_653 ? N1 Bi1 Br1 89.20(12) . 2_653 ? N1 Bi1 Br1 90.51(12) 2_653 2_653 ? C1 Bi1 Br1 88.660(15) . . ? N1 Bi1 Br1 90.51(12) . . ? N1 Bi1 Br1 89.20(12) 2_653 . ? Br1 Bi1 Br1 177.32(3) 2_653 . ? C1 Bi1 Br1 145.303(10) . 5_664 ? N1 Bi1 Br1 65.40(11) . 5_664 ? N1 Bi1 Br1 126.45(11) 2_653 5_664 ? Br1 Bi1 Br1 105.66(2) 2_653 5_664 ? Br1 Bi1 Br1 76.62(2) . 5_664 ? C1 Bi1 Br1 145.303(10) . 6_565 ? N1 Bi1 Br1 126.44(11) . 6_565 ? N1 Bi1 Br1 65.40(11) 2_653 6_565 ? Br1 Bi1 Br1 76.62(2) 2_653 6_565 ? Br1 Bi1 Br1 105.66(2) . 6_565 ? Br1 Bi1 Br1 69.39(2) 5_664 6_565 ? C9 N1 C5 117.2(6) . . ? C9 N1 Bi1 119.5(4) . . ? C5 N1 Bi1 123.3(4) . . ? C2 C1 C2 119.5(8) . 2_653 ? C2 C1 Bi1 120.2(4) . . ? C2 C1 Bi1 120.2(4) 2_653 . ? C3 C2 C1 119.8(6) . . ? C4 C3 C2 121.0(6) . . ? C3 C4 C3 119.0(9) 2_653 . ? N1 C5 C6 123.2(6) . . ? C5 C6 C7 119.8(6) . . ? C6 C7 C8 117.9(6) . . ? C9 C8 C7 119.4(7) . . ? N1 C9 C8 122.5(7) . . ? _refine_diff_density_max 2.559 _refine_diff_density_min -2.259 _refine_diff_density_rms 0.221 #======================================================================= data_9 #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 125 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H32 Bi Cl3 N2' _chemical_formula_weight 663.85 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.891(3) _cell_length_b 8.996(2) _cell_length_c 17.280(5) _cell_angle_alpha 90.00(2) _cell_angle_beta 98.59(2) _cell_angle_gamma 90.00(2) _cell_volume 2596.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 125 _cell_measurement_theta_min 14.610 _cell_measurement_theta_max 336.550 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method ? _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 7.113 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.704296 _exptl_absorpt_correction_T_max 0.862084 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 15965 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.0999 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5926 _reflns_number_observed 3968 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0178P)^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 'calculated' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00086(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5926 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_obs 0.0419 _refine_ls_wR_factor_all 0.0715 _refine_ls_wR_factor_obs 0.0591 _refine_ls_goodness_of_fit_all 0.993 _refine_ls_goodness_of_fit_obs 1.014 _refine_ls_restrained_S_all 0.993 _refine_ls_restrained_S_obs 1.014 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.208951(15) -0.77227(2) 0.77095(2) 0.02026(8) Uani 1 d . . Cl1 Cl 0.30256(12) -0.9693(2) 0.85135(13) 0.0408(5) Uani 1 d . . Cl2 Cl 0.08850(10) -0.9478(2) 0.72486(11) 0.0306(4) Uani 1 d . . Cl3 Cl 0.12030(10) -0.5350(2) 0.69947(10) 0.0274(4) Uani 1 d . . N1 N 0.3208(3) -0.5706(6) 0.8229(3) 0.0239(13) Uani 1 d . . N2 N -0.0462(3) -0.6687(6) 0.6303(3) 0.0271(14) Uani 1 d . . H2A H -0.0038(3) -0.6560(6) 0.6660(3) 0.032 Uiso 1 calc R . C1 C 0.1561(3) -0.7221(7) 0.8795(4) 0.0210(13) Uani 1 d . . C2 C 0.0743(4) -0.6889(6) 0.8746(4) 0.024(2) Uani 1 d . . H2B H 0.0412(4) -0.6860(6) 0.8251(4) 0.029 Uiso 1 calc R . C3 C 0.0419(4) -0.6602(7) 0.9427(5) 0.032(2) Uani 1 d . . H3A H -0.0135(4) -0.6384(7) 0.9395(5) 0.038 Uiso 1 calc R . C4 C 0.0886(4) -0.6632(7) 1.0132(4) 0.030(2) Uani 1 d . . H4A H 0.0659(4) -0.6428(7) 1.0591(4) 0.036 Uiso 1 calc R . C5 C 0.1699(4) -0.6958(7) 1.0192(4) 0.032(2) Uani 1 d . . H5A H 0.2026(4) -0.6984(7) 1.0689(4) 0.038 Uiso 1 calc R . C6 C 0.2023(4) -0.7241(7) 0.9525(3) 0.0222(14) Uani 1 d . . H6A H 0.2578(4) -0.7457(7) 0.9566(3) 0.027 Uiso 1 calc R . C7 C 0.3139(4) -0.4298(7) 0.7947(4) 0.024(2) Uani 1 d . . H7A H 0.2646(4) -0.4006(7) 0.7647(4) 0.029 Uiso 1 calc R . C8 C 0.3746(4) -0.3275(7) 0.8075(4) 0.027(2) Uani 1 d . . H8A H 0.3663(4) -0.2302(7) 0.7864(4) 0.033 Uiso 1 calc R . C9 C 0.4480(4) -0.3643(7) 0.8509(4) 0.022(2) Uani 1 d . . C10 C 0.4536(4) -0.5073(7) 0.8823(4) 0.028(2) Uani 1 d . . H10A H 0.5012(4) -0.5377(7) 0.9149(4) 0.033 Uiso 1 calc R . C11 C 0.3899(4) -0.6052(7) 0.8662(4) 0.029(2) Uani 1 d . . H11A H 0.3962(4) -0.7027(7) 0.8873(4) 0.035 Uiso 1 calc R . C12 C 0.5163(3) -0.2542(7) 0.8654(4) 0.026(2) Uani 1 d . . C13 C 0.5949(5) -0.3289(9) 0.8660(9) 0.126(6) Uani 1 d . . H13A H 0.6379(5) -0.2550(9) 0.8755(9) 0.189 Uiso 1 calc R . H13B H 0.5963(5) -0.3769(9) 0.8153(9) 0.189 Uiso 1 calc R . H13C H 0.6024(5) -0.4039(9) 0.9076(9) 0.189 Uiso 1 calc R . C14 C 0.5074(5) -0.1288(10) 0.8062(6) 0.087(4) Uani 1 d . . H14A H 0.4555(5) -0.0800(10) 0.8060(6) 0.131 Uiso 1 calc R . H14B H 0.5105(5) -0.1690(10) 0.7540(6) 0.131 Uiso 1 calc R . H14C H 0.5505(5) -0.0563(10) 0.8202(6) 0.131 Uiso 1 calc R . C15 C 0.5132(6) -0.1803(11) 0.9444(5) 0.096(4) Uani 1 d . . H15A H 0.4613(6) -0.1313(11) 0.9437(5) 0.144 Uiso 1 calc R . H15B H 0.5561(6) -0.1063(11) 0.9546(5) 0.144 Uiso 1 calc R . H15C H 0.5203(6) -0.2558(11) 0.9858(5) 0.144 Uiso 1 calc R . C16 C -0.0938(4) -0.7848(8) 0.6356(4) 0.033(2) Uani 1 d . . H16A H -0.0817(4) -0.8528(8) 0.6778(4) 0.039 Uiso 1 calc R . C17 C -0.1593(4) -0.8070(7) 0.5818(4) 0.029(2) Uani 1 d . . H17A H -0.1929(4) -0.8902(7) 0.5865(4) 0.035 Uiso 1 calc R . C18 C -0.1781(3) -0.7088(7) 0.5191(4) 0.0183(14) Uani 1 d . . C19 C -0.1268(4) -0.5899(7) 0.5159(4) 0.030(2) Uani 1 d . . H19A H -0.1369(4) -0.5201(7) 0.4743(4) 0.036 Uiso 1 calc R . C20 C -0.0612(4) -0.5725(7) 0.5725(4) 0.027(2) Uani 1 d . . H20A H -0.0263(4) -0.4903(7) 0.5700(4) 0.033 Uiso 1 calc R . C21 C -0.2504(4) -0.7320(7) 0.4545(4) 0.0248(15) Uani 1 d . . C22 C -0.3142(4) -0.8304(8) 0.4851(5) 0.047(2) Uani 1 d . . H22A H -0.2904(4) -0.9265(8) 0.5022(5) 0.070 Uiso 1 calc R . H22B H -0.3592(4) -0.8462(8) 0.4431(5) 0.070 Uiso 1 calc R . H22C H -0.3332(4) -0.7809(8) 0.5293(5) 0.070 Uiso 1 calc R . C23 C -0.2880(4) -0.5828(7) 0.4280(5) 0.039(2) Uani 1 d . . H23A H -0.3074(4) -0.5340(7) 0.4723(5) 0.058 Uiso 1 calc R . H23B H -0.3330(4) -0.5990(7) 0.3860(5) 0.058 Uiso 1 calc R . H23C H -0.2479(4) -0.5196(7) 0.4088(5) 0.058 Uiso 1 calc R . C24 C -0.2199(4) -0.8096(7) 0.3862(4) 0.037(2) Uani 1 d . . H24A H -0.1958(4) -0.9052(7) 0.4038(4) 0.055 Uiso 1 calc R . H24B H -0.1796(4) -0.7471(7) 0.3668(4) 0.055 Uiso 1 calc R . H24C H -0.2646(4) -0.8265(7) 0.3440(4) 0.055 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 Bi1 0.01910(12) 0.02287(13) 0.01941(13) -0.00233(15) 0.00479(9) - 0.00015(13) Cl1 0.0401(12) 0.0337(10) 0.0481(13) 0.0039(10) 0.0053(11) 0.0149(8) Cl2 0.0328(10) 0.0316(9) 0.0268(10) -0.0025(8) 0.0024(9) -0.0118(8) Cl3 0.0260(9) 0.0293(9) 0.0256(10) 0.0022(8) -0.0007(8) -0.0058(7) N1 0.020(3) 0.029(3) 0.023(3) 0.000(3) 0.003(3) 0.000(2) N2 0.022(3) 0.037(3) 0.022(3) -0.002(3) 0.001(3) -0.005(3) C1 0.025(3) 0.020(3) 0.018(3) 0.003(3) 0.001(3) 0.004(3) C2 0.022(4) 0.028(4) 0.020(4) 0.001(3) 0.002(3) 0.005(3) C3 0.028(4) 0.024(4) 0.048(5) -0.002(4) 0.020(4) 0.002(3) C4 0.046(5) 0.026(4) 0.022(4) -0.005(3) 0.016(4) -0.004(3) C5 0.050(5) 0.028(4) 0.018(4) -0.004(3) 0.004(4) -0.007(3) C6 0.025(3) 0.021(3) 0.020(3) 0.006(3) 0.001(3) 0.001(3) C7 0.019(4) 0.028(4) 0.024(4) 0.006(3) -0.005(3) 0.005(3) C8 0.025(4) 0.022(3) 0.034(4) 0.002(3) 0.003(4) 0.001(3) C9 0.018(3) 0.026(4) 0.023(4) -0.001(3) 0.003(3) 0.002(3) C10 0.014(3) 0.040(4) 0.027(4) 0.004(4) -0.001(3) -0.006(3) C11 0.028(4) 0.027(4) 0.030(4) 0.009(3) -0.005(4) 0.003(3) C12 0.017(3) 0.025(4) 0.035(4) -0.002(3) 0.001(3) -0.007(3) C13 0.021(5) 0.048(6) 0.313(20) -0.018(8) 0.039(8) -0.011(4) C14 0.052(6) 0.095(7) 0.106(10) 0.052(7) -0.012(6) -0.047(5) C15 0.134(10) 0.105(8) 0.050(7) -0.022(6) 0.014(7) -0.094(8) C16 0.031(4) 0.037(4) 0.029(4) 0.005(4) -0.002(3) -0.002(4) C17 0.031(4) 0.019(4) 0.038(5) 0.001(3) 0.008(4) -0.006(3) C18 0.015(3) 0.017(3) 0.022(4) -0.002(3) -0.001(3) 0.003(3) C19 0.029(4) 0.024(4) 0.037(5) 0.008(3) 0.004(4) 0.001(3) C20 0.028(4) 0.023(4) 0.029(4) 0.000(3) 0.001(4) -0.006(3) C21 0.026(3) 0.022(3) 0.026(4) 0.003(3) 0.002(3) 0.002(3) C22 0.025(4) 0.065(5) 0.047(5) 0.011(5) -0.007(4) -0.015(4) C23 0.027(4) 0.046(5) 0.039(5) -0.008(4) -0.008(4) 0.014(3) C24 0.038(4) 0.035(4) 0.035(5) -0.003(4) -0.002(4) 0.002(3) #======================================================================= # 10. 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 Bi1 C1 2.241(6) . ? Bi1 Cl2 2.604(2) . ? Bi1 Cl1 2.630(2) . ? Bi1 N1 2.676(5) . ? Bi1 Cl3 2.788(2) . ? N1 C11 1.326(8) . ? N1 C7 1.355(7) . ? N2 C20 1.317(8) . ? N2 C16 1.330(8) . ? C1 C6 1.380(8) . ? C1 C2 1.403(8) . ? C2 C3 1.395(9) . ? C3 C4 1.349(10) . ? C4 C5 1.392(9) . ? C5 C6 1.371(8) . ? C7 C8 1.371(8) . ? C8 C9 1.390(9) . ? C9 C10 1.394(8) . ? C9 C12 1.513(8) . ? C10 C11 1.386(9) . ? C12 C13 1.487(9) . ? C12 C14 1.515(10) . ? C12 C15 1.526(10) . ? C16 C17 1.350(9) . ? C17 C18 1.397(9) . ? C18 C19 1.383(8) . ? C18 C21 1.540(8) . ? C19 C20 1.373(9) . ? C21 C23 1.526(8) . ? C21 C24 1.526(8) . ? C21 C22 1.548(8) . ? 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 C1 Bi1 Cl2 89.3(2) . . ? C1 Bi1 Cl1 88.7(2) . . ? Cl2 Bi1 Cl1 97.66(6) . . ? C1 Bi1 N1 86.1(2) . . ? Cl2 Bi1 N1 173.63(11) . . ? Cl1 Bi1 N1 86.64(13) . . ? C1 Bi1 Cl3 87.8(2) . . ? Cl2 Bi1 Cl3 89.17(5) . . ? Cl1 Bi1 Cl3 172.28(6) . . ? N1 Bi1 Cl3 86.26(12) . . ? C11 N1 C7 116.3(5) . . ? C11 N1 Bi1 123.2(4) . . ? C7 N1 Bi1 119.6(4) . . ? C20 N2 C16 121.3(6) . . ? C6 C1 C2 118.4(6) . . ? C6 C1 Bi1 121.4(4) . . ? C2 C1 Bi1 120.2(5) . . ? C3 C2 C1 119.7(7) . . ? C4 C3 C2 120.5(6) . . ? C3 C4 C5 120.6(6) . . ? C6 C5 C4 119.3(7) . . ? C5 C6 C1 121.6(6) . . ? N1 C7 C8 123.2(6) . . ? C7 C8 C9 120.8(6) . . ? C8 C9 C10 115.7(6) . . ? C8 C9 C12 122.0(6) . . ? C10 C9 C12 122.3(6) . . ? C11 C10 C9 120.2(6) . . ? N1 C11 C10 123.8(6) . . ? C13 C12 C9 111.3(6) . . ? C13 C12 C14 109.8(7) . . ? C9 C12 C14 112.3(6) . . ? C13 C12 C15 109.9(9) . . ? C9 C12 C15 107.8(6) . . ? C14 C12 C15 105.5(7) . . ? N2 C16 C17 120.7(7) . . ? C16 C17 C18 120.6(6) . . ? C19 C18 C17 116.6(6) . . ? C19 C18 C21 120.6(6) . . ? C17 C18 C21 122.7(5) . . ? C20 C19 C18 120.3(7) . . ? N2 C20 C19 120.5(6) . . ? C23 C21 C24 110.2(6) . . ? C23 C21 C18 110.4(5) . . ? C24 C21 C18 107.5(5) . . ? C23 C21 C22 109.0(5) . . ? C24 C21 C22 109.6(6) . . ? C18 C21 C22 110.3(5) . . ? _refine_diff_density_max 0.811 _refine_diff_density_min -1.046 _refine_diff_density_rms 0.191 #======================================================================= data_10 #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 121 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H17 Bi I N' _chemical_formula_weight 583.21 _chemical_melting_point ? _chemical_compound_source ? 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pca21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 10.786(2) _cell_length_b 9.463(2) _cell_length_c 17.611(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1797.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 121 _cell_measurement_theta_min 17.450 _cell_measurement_theta_max 336.550 _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.155 _exptl_crystal_density_method ? _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 11.520 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.334411 _exptl_absorpt_correction_T_max 0.694165 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 10964 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0832 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3981 _reflns_number_observed 2928 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0138P)^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 'calculated' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00053(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.043(5) _refine_ls_number_reflns 3981 _refine_ls_number_parameters 192 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_obs 0.0303 _refine_ls_wR_factor_all 0.0548 _refine_ls_wR_factor_obs 0.0503 _refine_ls_goodness_of_fit_all 0.801 _refine_ls_goodness_of_fit_obs 0.864 _refine_ls_restrained_S_all 0.801 _refine_ls_restrained_S_obs 0.864 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 1.40180(2) 0.64315(3) 0.24925(2) 0.02608(8) Uani 1 d . . I1 I 1.58312(5) 0.52821(6) 0.36465(4) 0.0346(2) Uani 1 d . . N1 N 1.2576(6) 0.7663(7) 0.1509(4) 0.026(2) Uani 1 d . . C1 C 1.5567(7) 0.6716(8) 0.1636(5) 0.019(2) Uani 1 d . . C2 C 1.5317(8) 0.6508(9) 0.0887(5) 0.025(2) Uani 1 d . . H2A H 1.4484(8) 0.6350(9) 0.0735(5) 0.030 Uiso 1 calc R . C3 C 1.6255(8) 0.6520(10) 0.0329(5) 0.030(2) Uani 1 d . . H3A H 1.6056(8) 0.6381(10) -0.0191(5) 0.036 Uiso 1 calc R . C4 C 1.7454(8) 0.6734(9) 0.0548(5) 0.033(2) Uani 1 d . . H4A H 1.8101(8) 0.6711(9) 0.0183(5) 0.040 Uiso 1 calc R . C5 C 1.7727(8) 0.6987(8) 0.1308(5) 0.029(2) Uani 1 d . . H5A H 1.8556(8) 0.7186(8) 0.1457(5) 0.035 Uiso 1 calc R . C6 C 1.6796(7) 0.6949(8) 0.1849(5) 0.026(2) Uani 1 d . . H6A H 1.6996(7) 0.7082(8) 0.2369(5) 0.031 Uiso 1 calc R . C7 C 1.4080(7) 0.8643(8) 0.2953(4) 0.024(2) Uani 1 d . . C8 C 1.3079(8) 0.9096(11) 0.3398(5) 0.035(2) Uani 1 d . . H8A H 1.2483(8) 0.8429(11) 0.3569(5) 0.042 Uiso 1 calc R . C9 C 1.2951(8) 1.0489(11) 0.3588(6) 0.043(3) Uani 1 d . . H9A H 1.2258(8) 1.0785(11) 0.3881(6) 0.052 Uiso 1 calc R . C10 C 1.3807(8) 1.1453(11) 0.3360(6) 0.042(3) Uani 1 d . . H10A H 1.3718(8) 1.2416(11) 0.3502(6) 0.051 Uiso 1 calc R . C11 C 1.4805(8) 1.1042(10) 0.2924(5) 0.033(2) Uani 1 d . . H11A H 1.5411(8) 1.1714(10) 0.2773(5) 0.039 Uiso 1 calc R . C12 C 1.4916(7) 0.9656(9) 0.2709(5) 0.031(2) Uani 1 d . . H12A H 1.5580(7) 0.9385(9) 0.2386(5) 0.037 Uiso 1 calc R . C13 C 1.1832(9) 0.6814(9) 0.1109(6) 0.043(3) Uani 1 d . . H13A H 1.1902(9) 0.5824(9) 0.1188(6) 0.051 Uiso 1 calc R . C14 C 1.0960(9) 0.7285(9) 0.0582(6) 0.035(3) Uani 1 d . . H14A H 1.0489(9) 0.6629(9) 0.0294(6) 0.042 Uiso 1 calc R . C15 C 1.0789(7) 0.8749(10) 0.0485(5) 0.030(2) Uani 1 d . . C16 C 1.1550(8) 0.9606(10) 0.0924(5) 0.032(2) Uani 1 d . . H16A H 1.1480(8) 1.0604(10) 0.0885(5) 0.039 Uiso 1 calc R . C17 C 1.2413(9) 0.9021(9) 0.1419(5) 0.034(2) Uani 1 d . . H17A H 1.2913(9) 0.9646(9) 0.1709(5) 0.040 Uiso 1 calc R . C18 C 0.9840(8) 0.9286(9) -0.0039(5) 0.035(2) Uani 1 d . . H18A H 0.9421(8) 0.8490(9) -0.0285(5) 0.053 Uiso 1 calc R . H18B H 1.0233(8) 0.9881(9) -0.0426(5) 0.053 Uiso 1 calc R . H18C H 0.9232(8) 0.9847(9) 0.0245(5) 0.053 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 Bi1 0.02108(12) 0.02638(15) 0.0308(2) -0.0016(2) 0.0006(3) -0.00383(15) I1 0.0357(3) 0.0400(4) 0.0282(3) 0.0064(3) -0.0002(3) -0.0001(3) N1 0.032(4) 0.016(4) 0.028(5) -0.002(3) -0.002(3) -0.005(3) C1 0.026(4) 0.014(5) 0.018(5) -0.004(3) -0.001(3) 0.004(3) C2 0.033(5) 0.016(4) 0.025(5) 0.002(4) -0.011(4) -0.001(4) C3 0.045(6) 0.022(5) 0.024(5) 0.007(5) 0.002(4) 0.000(5) C4 0.038(5) 0.020(5) 0.040(6) 0.001(4) 0.018(5) -0.005(4) C5 0.031(5) 0.026(5) 0.031(6) -0.004(4) -0.003(4) -0.001(4) C6 0.029(5) 0.022(5) 0.028(5) -0.009(4) 0.003(4) -0.002(4) C7 0.021(4) 0.024(4) 0.027(5) 0.002(4) -0.008(4) -0.004(4) C8 0.032(5) 0.041(6) 0.031(6) -0.002(5) 0.008(4) -0.001(5) C9 0.025(5) 0.065(8) 0.040(6) -0.028(6) 0.012(5) 0.006(5) C10 0.042(6) 0.040(6) 0.045(6) -0.023(5) -0.019(5) 0.027(5) C11 0.030(5) 0.038(6) 0.029(6) -0.007(5) -0.018(4) -0.002(4) C12 0.018(4) 0.039(6) 0.034(7) -0.007(4) 0.002(4) -0.003(4) C13 0.044(6) 0.019(5) 0.066(8) -0.003(5) -0.020(6) 0.010(4) C14 0.025(5) 0.017(5) 0.063(8) -0.004(5) -0.018(5) -0.005(5) C15 0.017(4) 0.036(6) 0.037(6) -0.004(5) 0.015(4) -0.003(4) C16 0.035(5) 0.026(6) 0.036(6) 0.002(4) -0.004(5) -0.002(5) C17 0.047(6) 0.027(5) 0.027(6) -0.006(4) -0.005(5) -0.010(5) C18 0.025(5) 0.036(6) 0.045(7) 0.007(5) 0.007(4) 0.006(5) #======================================================================= # 10. 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 Bi1 C7 2.246(8) . ? Bi1 C1 2.267(8) . ? Bi1 N1 2.604(7) . ? Bi1 I1 3.0229(8) . ? Bi1 I1 4.3099(9) 3_465 ? I1 Bi1 4.3099(9) 3_565 ? N1 C17 1.307(10) . ? N1 C13 1.337(10) . ? C1 C2 1.359(10) . ? C1 C6 1.396(10) . ? C2 C3 1.411(11) . ? C3 C4 1.365(11) . ? C4 C5 1.391(12) . ? C5 C6 1.384(11) . ? C7 C12 1.385(10) . ? C7 C8 1.401(11) . ? C8 C9 1.367(12) . ? C9 C10 1.359(13) . ? C10 C11 1.378(12) . ? C11 C12 1.370(12) . ? C13 C14 1.394(12) . ? C14 C15 1.408(12) . ? C15 C16 1.389(12) . ? C15 C18 1.469(12) . ? C16 C17 1.390(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 Bi1 C1 96.2(3) . . ? C7 Bi1 N1 80.8(2) . . ? C1 Bi1 N1 86.8(2) . . ? C7 Bi1 I1 94.2(2) . . ? C1 Bi1 I1 90.8(2) . . ? N1 Bi1 I1 174.21(15) . . ? C7 Bi1 I1 101.8(2) . 3_465 ? C1 Bi1 I1 161.1(2) . 3_465 ? N1 Bi1 I1 90.32(14) . 3_465 ? I1 Bi1 I1 93.64(2) . 3_465 ? Bi1 I1 Bi1 109.53(2) . 3_565 ? C17 N1 C13 116.5(8) . . ? C17 N1 Bi1 126.9(6) . . ? C13 N1 Bi1 116.1(6) . . ? C2 C1 C6 118.1(7) . . ? C2 C1 Bi1 118.8(6) . . ? C6 C1 Bi1 122.7(6) . . ? C1 C2 C3 122.2(8) . . ? C4 C3 C2 118.9(8) . . ? C3 C4 C5 119.9(9) . . ? C6 C5 C4 120.2(8) . . ? C5 C6 C1 120.6(8) . . ? C12 C7 C8 117.6(8) . . ? C12 C7 Bi1 123.5(6) . . ? C8 C7 Bi1 117.7(6) . . ? C9 C8 C7 120.6(9) . . ? C10 C9 C8 120.4(9) . . ? C9 C10 C11 120.4(9) . . ? C12 C11 C10 119.5(9) . . ? C11 C12 C7 121.3(8) . . ? N1 C13 C14 124.3(8) . . ? C13 C14 C15 118.9(8) . . ? C16 C15 C14 115.4(8) . . ? C16 C15 C18 124.0(9) . . ? C14 C15 C18 120.5(8) . . ? C15 C16 C17 120.8(9) . . ? N1 C17 C16 123.9(9) . . ? _refine_diff_density_max 0.890 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.144 #======================================================================= data_12 #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 64 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H23 Bi Br2 N2' _chemical_formula_weight 660.20 _chemical_melting_point ? _chemical_compound_source ? 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3904(4) _cell_length_b 18.2220(4) _cell_length_c 9.3437(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.252(2) _cell_angle_gamma 90.00 _cell_volume 2363.82(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 64 _cell_measurement_theta_min 17.501 _cell_measurement_theta_max 336.462 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method ? _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 10.844 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.382021 _exptl_absorpt_correction_T_max 0.491507 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 14617 _diffrn_reflns_av_R_equivalents 0.1186 _diffrn_reflns_av_sigmaI/netI 0.1669 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5347 _reflns_number_observed 2500 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0600P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5347 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1746 _refine_ls_R_factor_obs 0.0656 _refine_ls_wR_factor_all 0.1691 _refine_ls_wR_factor_obs 0.1131 _refine_ls_goodness_of_fit_all 1.011 _refine_ls_goodness_of_fit_obs 1.009 _refine_ls_restrained_S_all 1.011 _refine_ls_restrained_S_obs 1.009 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.14762(4) 0.49720(4) 0.66345(6) 0.0288(2) Uani 1 d . . Br1 Br 0.04703(14) 0.57327(10) 0.3764(2) 0.0388(5) Uani 1 d . . Br2 Br 0.31858(13) 0.57168(12) 0.6791(2) 0.0467(5) Uani 1 d . . Br3 Br 0.22102(13) 0.42048(11) 0.9249(2) 0.0427(5) Uani 1 d . . C1 C 0.1001(11) 0.5899(9) 0.7851(15) 0.023(3) Uani 1 d . . C2 C 0.0510(11) 0.5777(10) 0.8898(18) 0.031(4) Uani 1 d . . H2A H 0.0386(11) 0.5284(10) 0.9124(18) 0.037 Uiso 1 calc R . C3 C 0.0187(11) 0.6328(11) 0.9638(18) 0.034(4) Uani 1 d . . H3A H -0.0145(11) 0.6216(11) 1.0364(18) 0.040 Uiso 1 calc R . C4 C 0.0349(11) 0.7052(10) 0.9319(20) 0.038(5) Uani 1 d . . H4A H 0.0135(11) 0.7443(10) 0.9824(20) 0.045 Uiso 1 calc R . C5 C 0.0822(12) 0.7188(9) 0.8263(19) 0.035(4) Uani 1 d . . H5A H 0.0930(12) 0.7683(9) 0.8029(19) 0.042 Uiso 1 calc R . C6 C 0.1153(10) 0.6632(9) 0.7520(19) 0.029(4) Uani 1 d . . H6A H 0.1481(10) 0.6746(9) 0.6789(19) 0.035 Uiso 1 calc R . N1 N 0.3484(9) 0.3498(8) 0.5319(15) 0.032(3) Uani 1 d . . H1A H 0.4103(9) 0.3494(8) 0.5775(15) 0.038 Uiso 1 calc R . C7 C 0.3162(11) 0.3997(10) 0.4240(18) 0.033(4) Uani 1 d . . C8 C 0.2195(12) 0.4028(11) 0.3538(19) 0.041(5) Uani 1 d . . H8A H 0.1968(12) 0.4392(11) 0.2800(19) 0.049 Uiso 1 calc R . C9 C 0.1558(12) 0.3555(13) 0.3871(20) 0.050(6) Uani 1 d . . H9A H 0.0889(12) 0.3586(13) 0.3390(20) 0.060 Uiso 1 calc R . C10 C 0.1918(11) 0.3015(12) 0.4953(19) 0.041(5) Uani 1 d . . H10A H 0.1496(11) 0.2654(12) 0.5164(19) 0.050 Uiso 1 calc R . C11 C 0.2916(13) 0.3007(10) 0.5736(20) 0.040(5) Uani 1 d . . C12 C 0.3880(14) 0.4485(12) 0.3852(22) 0.053(6) Uani 1 d . . H12A H 0.4523(14) 0.4371(12) 0.4485(22) 0.079 Uiso 1 calc R . H12B H 0.3722(14) 0.4997(12) 0.4005(22) 0.079 Uiso 1 calc R . H12C H 0.3872(14) 0.4411(12) 0.2810(22) 0.079 Uiso 1 calc R . C13 C 0.3340(15) 0.2445(11) 0.6870(20) 0.056(6) Uani 1 d . . H13A H 0.4030(15) 0.2541(11) 0.7267(20) 0.083 Uiso 1 calc R . H13B H 0.3248(15) 0.1957(11) 0.6415(20) 0.083 Uiso 1 calc R . H13C H 0.3022(15) 0.2467(11) 0.7677(20) 0.083 Uiso 1 calc R . N2 N 0.5378(9) 0.3508(8) 0.6910(15) 0.034(3) Uani 1 d . . C14 C 0.5613(13) 0.3884(9) 0.8161(19) 0.037(4) Uani 1 d . . C15 C 0.6536(16) 0.4004(11) 0.8918(24) 0.051(5) Uani 1 d . . H15A H 0.6680(16) 0.4258(11) 0.9839(24) 0.061 Uiso 1 calc R . C16 C 0.7250(16) 0.3763(16) 0.8362(30) 0.087(10) Uani 1 d . . H16A H 0.7902(16) 0.3865(16) 0.8860(30) 0.104 Uiso 1 calc R . C17 C 0.7022(14) 0.3360(15) 0.7038(32) 0.078(9) Uani 1 d . . H17A H 0.7517(14) 0.3166(15) 0.6645(32) 0.093 Uiso 1 calc R . C18 C 0.6040(14) 0.3248(10) 0.6298(22) 0.043(5) Uani 1 d . . C19 C 0.4798(16) 0.4160(13) 0.8816(21) 0.072(7) Uani 1 d . . H19A H 0.4173(16) 0.4032(13) 0.8144(21) 0.107 Uiso 1 calc R . H19B H 0.4845(16) 0.4694(13) 0.8937(21) 0.107 Uiso 1 calc R . H19C H 0.4859(16) 0.3929(13) 0.9783(21) 0.107 Uiso 1 calc R . C20 C 0.5695(16) 0.2827(12) 0.4870(25) 0.072(7) Uani 1 d . . H20A H 0.4990(16) 0.2822(12) 0.4570(25) 0.108 Uiso 1 calc R . H20B H 0.5937(16) 0.2323(12) 0.5015(25) 0.108 Uiso 1 calc R . H20C H 0.5936(16) 0.3064(12) 0.4096(25) 0.108 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 Bi1 0.0368(3) 0.0263(3) 0.0235(3) -0.0008(3) 0.0080(2) 0.0027(4) Br1 0.0538(11) 0.0321(10) 0.0263(9) 0.0047(8) 0.0033(8) -0.0105(9) Br2 0.0392(11) 0.0540(14) 0.0526(12) 0.0078(10) 0.0220(10) 0.0039(10) Br3 0.0434(11) 0.0443(12) 0.0394(11) 0.0149(9) 0.0089(9) 0.0070(9) C1 0.030(9) 0.027(9) 0.013(7) -0.001(6) 0.008(7) 0.008(7) C2 0.027(9) 0.036(10) 0.029(9) -0.002(8) 0.005(7) -0.001(8) C3 0.019(9) 0.057(13) 0.028(10) 0.006(8) 0.012(7) 0.019(8) C4 0.022(9) 0.042(12) 0.045(11) -0.016(9) 0.002(8) 0.009(8) C5 0.045(11) 0.022(9) 0.043(11) -0.021(8) 0.018(9) -0.008(8) C6 0.019(8) 0.033(10) 0.039(10) -0.011(8) 0.012(7) 0.004(7) N1 0.026(7) 0.031(9) 0.034(8) 0.002(7) 0.001(6) -0.008(7) C7 0.027(9) 0.043(12) 0.025(9) -0.013(8) -0.001(8) -0.004(8) C8 0.027(10) 0.050(13) 0.035(11) -0.012(9) -0.013(8) 0.017(9) C9 0.016(9) 0.088(18) 0.039(12) -0.013(11) -0.004(8) 0.015(10) C10 0.013(8) 0.079(16) 0.033(10) -0.019(10) 0.008(8) -0.010(9) C11 0.042(11) 0.037(12) 0.040(11) 0.003(9) 0.009(9) 0.007(9) C12 0.051(12) 0.054(15) 0.051(12) 0.021(11) 0.009(10) 0.000(11) C13 0.081(15) 0.047(13) 0.032(11) 0.021(9) 0.001(11) -0.021(12) N2 0.025(8) 0.039(9) 0.028(8) -0.005(7) -0.007(6) 0.003(7) C14 0.044(11) 0.026(10) 0.033(10) 0.005(8) -0.005(9) 0.011(8) C15 0.054(14) 0.038(13) 0.054(14) 0.006(10) 0.002(12) -0.002(10) C16 0.040(14) 0.106(24) 0.082(20) 0.018(17) -0.041(14) -0.025(14) C17 0.021(12) 0.083(21) 0.127(24) 0.040(18) 0.015(13) 0.014(11) C18 0.044(11) 0.026(11) 0.055(13) 0.004(9) 0.006(10) -0.007(9) C19 0.090(17) 0.086(19) 0.032(12) -0.018(12) 0.005(12) 0.026(15) C20 0.087(17) 0.057(16) 0.074(17) -0.028(13) 0.026(14) 0.015(14) #======================================================================= # 10. 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 Bi1 C1 2.241(14) . ? Bi1 Br3 2.771(2) . ? Bi1 Br2 2.780(2) . ? Bi1 Br1 3.014(2) 3_566 ? Bi1 Br1 3.028(2) . ? Br1 Bi1 3.014(2) 3_566 ? C1 C2 1.37(2) . ? C1 C6 1.40(2) . ? C2 C3 1.37(2) . ? C3 C4 1.38(2) . ? C4 C5 1.36(2) . ? C5 C6 1.38(2) . ? N1 C11 1.34(2) . ? N1 C7 1.35(2) . ? C7 C8 1.37(2) . ? C7 C12 1.48(2) . ? C8 C9 1.35(3) . ? C9 C10 1.41(3) . ? C10 C11 1.43(2) . ? C11 C13 1.49(2) . ? N2 C14 1.32(2) . ? N2 C18 1.32(2) . ? C14 C15 1.35(3) . ? C14 C19 1.54(3) . ? C15 C16 1.34(3) . ? C16 C17 1.40(4) . ? C17 C18 1.42(3) . ? C18 C20 1.50(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 C1 Bi1 Br3 91.7(4) . . ? C1 Bi1 Br2 89.4(4) . . ? Br3 Bi1 Br2 94.20(6) . . ? C1 Bi1 Br1 89.2(4) . 3_566 ? Br3 Bi1 Br1 91.17(5) . 3_566 ? Br2 Bi1 Br1 174.49(6) . 3_566 ? C1 Bi1 Br1 88.0(4) . . ? Br3 Bi1 Br1 173.89(6) . . ? Br2 Bi1 Br1 91.90(6) . . ? Br1 Bi1 Br1 82.72(5) 3_566 . ? Bi1 Br1 Bi1 97.28(5) 3_566 . ? C2 C1 C6 116.9(14) . . ? C2 C1 Bi1 121.6(12) . . ? C6 C1 Bi1 121.4(11) . . ? C1 C2 C3 123.4(17) . . ? C2 C3 C4 119.5(16) . . ? C5 C4 C3 118.2(16) . . ? C4 C5 C6 122.4(17) . . ? C5 C6 C1 119.6(15) . . ? C11 N1 C7 123.6(15) . . ? N1 C7 C8 119.4(17) . . ? N1 C7 C12 117.7(15) . . ? C8 C7 C12 122.9(17) . . ? C9 C8 C7 121.8(18) . . ? C8 C9 C10 117.8(16) . . ? C9 C10 C11 120.3(17) . . ? N1 C11 C10 117.0(17) . . ? N1 C11 C13 120.0(16) . . ? C10 C11 C13 122.7(17) . . ? C14 N2 C18 121.6(15) . . ? N2 C14 C15 122.4(18) . . ? N2 C14 C19 118.4(16) . . ? C15 C14 C19 119.1(18) . . ? C16 C15 C14 119.5(20) . . ? C15 C16 C17 119.3(19) . . ? C16 C17 C18 118.5(22) . . ? N2 C18 C17 118.6(20) . . ? N2 C18 C20 117.4(17) . . ? C17 C18 C20 124.0(21) . . ? _refine_diff_density_max 2.191 _refine_diff_density_min -1.333 _refine_diff_density_rms 0.377 #======================================================================= data_13 [SbBr4Ph]2- #======================================================================= # 5. CHEMICAL DATA _publ_section_exptl_refinement ; Unit cell dimensions were determined from 378 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C34 H49 Br4 N3 Sb' _chemical_formula_weight 941.15 _chemical_melting_point ? _chemical_compound_source ? 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sb' 'Sb' -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #======================================================================= # 6. CRYSTAL DATA _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 11.189(2) _cell_length_b 11.824(2) _cell_length_c 14.931(3) _cell_angle_alpha 90.09(3) _cell_angle_beta 92.04(3) _cell_angle_gamma 105.96(3) _cell_volume 1897.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 378 _cell_measurement_theta_min 14.654 _cell_measurement_theta_max 336.550 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method ? _exptl_crystal_F_000 930 _exptl_absorpt_coefficient_mu 4.963 _exptl_absorpt_correction_type 'sadabs' _exptl_absorpt_correction_T_min 0.474064 _exptl_absorpt_correction_T_max 1.000000 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 19872 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8604 _reflns_number_observed 5405 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXTL (Siemens, 1995)' _computing_structure_refinement 'SHELXTL (Siemens, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995)' _computing_publication_material 'SHELXTL (Siemens, 1995)' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0272P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00052(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 8604 _refine_ls_number_parameters 398 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_obs 0.0344 _refine_ls_wR_factor_all 0.0752 _refine_ls_wR_factor_obs 0.0697 _refine_ls_goodness_of_fit_all 0.841 _refine_ls_goodness_of_fit_obs 0.995 _refine_ls_restrained_S_all 0.840 _refine_ls_restrained_S_obs 0.994 _refine_ls_shift/esd_max 0.015 _refine_ls_shift/esd_mean 0.001 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sb1 Sb 1.27163(3) 1.10405(2) 0.29954(2) 0.02392(9) Uani 1 d . . Br1 Br 1.11612(4) 0.92690(4) 0.40548(3) 0.02827(12) Uani 1 d . . Br2 Br 1.41026(4) 1.19842(4) 0.47103(3) 0.03470(13) Uani 1 d . . Br3 Br 1.41763(4) 1.27835(4) 0.19769(3) 0.03539(13) Uani 1 d . . Br4 Br 1.13476(4) 1.00960(4) 0.15526(3) 0.03525(13) Uani 1 d . . N1 N 0.7341(4) 1.0260(3) 0.3922(3) 0.0400(10) Uani 1 d . . H1A H 0.7289(4) 1.0014(3) 0.4465(3) 0.048 Uiso 1 calc R . N2 N 0.7098(4) 0.4775(3) 0.5258(3) 0.0421(11) Uani 1 d . . H2A H 0.7261(4) 0.5159(3) 0.4768(3) 0.051 Uiso 1 calc R . N3 N 0.7670(4) 0.5700(3) 0.3618(3) 0.0436(11) Uani 1 d . . C1 C 1.1506(4) 1.2174(3) 0.3212(3) 0.0221(9) Uani 1 d . . C2 C 1.1271(4) 1.2890(3) 0.2522(3) 0.0280(10) Uani 1 d . . H2B H 1.1612(4) 1.2863(3) 0.1966(3) 0.034 Uiso 1 calc R . C3 C 1.0533(4) 1.3639(4) 0.2661(3) 0.0335(11) Uani 1 d . . H3B H 1.0394(4) 1.4121(4) 0.2200(3) 0.040 Uiso 1 calc R . C4 C 1.0009(4) 1.3673(4) 0.3470(3) 0.0366(12) Uani 1 d . . H4A H 0.9517(4) 1.4179(4) 0.3560(3) 0.044 Uiso 1 calc R . C5 C 1.0212(4) 1.2955(4) 0.4156(3) 0.0364(12) Uani 1 d . . H5A H 0.9844(4) 1.2968(4) 0.4704(3) 0.044 Uiso 1 calc R . C6 C 1.0969(4) 1.2209(4) 0.4026(3) 0.0286(10) Uani 1 d . . H6A H 1.1112(4) 1.1734(4) 0.4490(3) 0.034 Uiso 1 calc R . C7 C 0.6504(4) 1.0800(4) 0.3609(3) 0.0416(13) Uani 1 d . . H7A H 0.5896(4) 1.0922(4) 0.3976(3) 0.050 Uiso 1 calc R . C8 C 0.6565(4) 1.1167(4) 0.2738(3) 0.0358(12) Uani 1 d . . H8A H 0.5988(4) 1.1541(4) 0.2517(3) 0.043 Uiso 1 calc R . C9 C 0.7470(4) 1.0995(3) 0.2173(3) 0.0252(10) Uani 1 d . . C10 C 0.8312(4) 1.0443(4) 0.2558(3) 0.0314(11) Uani 1 d . . H10A H 0.8938(4) 1.0310(4) 0.2213(3) 0.038 Uiso 1 calc R . C11 C 0.8236(4) 1.0090(4) 0.3437(3) 0.0396(12) Uani 1 d . . H11A H 0.8812(4) 0.9734(4) 0.3687(3) 0.048 Uiso 1 calc R . C12 C 0.7489(4) 1.1372(4) 0.1206(3) 0.0315(11) Uani 1 d . . C13 C 0.8621(5) 1.1216(4) 0.0746(3) 0.0436(13) Uani 1 d . . H13A H 0.8604(5) 1.1463(4) 0.0135(3) 0.065 Uiso 1 calc R . H13B H 0.8614(5) 1.0402(4) 0.0761(3) 0.065 Uiso 1 calc R . H13C H 0.9363(5) 1.1683(4) 0.1052(3) 0.065 Uiso 1 calc R . C14 C 0.7500(4) 1.2662(4) 0.1164(3) 0.0431(13) Uani 1 d . . H14A H 0.7512(4) 1.2903(4) 0.0550(3) 0.065 Uiso 1 calc R . H14B H 0.8226(4) 1.3134(4) 0.1484(3) 0.065 Uiso 1 calc R . H14C H 0.6768(4) 1.2764(4) 0.1432(3) 0.065 Uiso 1 calc R . C15 C 0.6318(5) 1.0618(4) 0.0718(3) 0.0528(15) Uani 1 d . . H15A H 0.6315(5) 1.0846(4) 0.0101(3) 0.079 Uiso 1 calc R . H15B H 0.5596(5) 1.0728(4) 0.0994(3) 0.079 Uiso 1 calc R . H15C H 0.6308(5) 0.9804(4) 0.0751(3) 0.079 Uiso 1 calc R . C16 C 0.7436(5) 0.3781(4) 0.5364(3) 0.0454(13) Uani 1 d . . H16A H 0.7839(5) 0.3513(4) 0.4909(3) 0.054 Uiso 1 calc R . C17 C 0.7190(4) 0.3157(4) 0.6138(3) 0.0401(12) Uani 1 d . . H17A H 0.7434(4) 0.2470(4) 0.6209(3) 0.048 Uiso 1 calc R . C18 C 0.6579(4) 0.3543(4) 0.6817(3) 0.0307(11) Uani 1 d . . C19 C 0.6248(4) 0.4577(4) 0.6668(3) 0.0363(12) Uani 1 d . . H19A H 0.5833(4) 0.4862(4) 0.7106(3) 0.044 Uiso 1 calc R . C20 C 0.6520(5) 0.5184(4) 0.5886(4) 0.0401(13) Uani 1 d . . H20A H 0.6299(5) 0.5879(4) 0.5798(4) 0.048 Uiso 1 calc R . C21 C 0.6290(6) 0.2850(5) 0.7679(4) 0.056(2) Uani 1 d . . C22 C 0.6515(28) 0.1741(20) 0.7737(16) 0.183(15) Uani 0.50 d P 1 C23 C 0.4645(15) 0.2373(18) 0.7554(14) 0.160(9) Uani 0.50 d P 1 C24 C 0.6228(23) 0.3684(17) 0.8428(13) 0.098(9) Uani 0.50 d PU 1 C22' C 0.5631(18) 0.3268(14) 0.8407(14) 0.062(5) Uani 0.50 d P 2 C23' C 0.7719(9) 0.2887(10) 0.8110(7) 0.049(3) Uani 0.50 d P 2 C24' C 0.5665(12) 0.1587(9) 0.7427(10) 0.047(3) Uani 0.50 d P 2 C25 C 0.6923(4) 0.5033(4) 0.3002(4) 0.0401(13) Uani 1 d . . H25A H 0.6320(4) 0.4375(4) 0.3190(4) 0.048 Uiso 1 calc R . C26 C 0.6989(4) 0.5259(4) 0.2090(3) 0.0380(12) Uani 1 d . . H26A H 0.6437(4) 0.4762(4) 0.1685(3) 0.046 Uiso 1 calc R . C27 C 0.7884(4) 0.6230(4) 0.1784(3) 0.0334(11) Uani 1 d . . C28 C 0.8652(4) 0.6929(4) 0.2439(3) 0.0442(13) Uani 1 d . . H28A H 0.9261(4) 0.7598(4) 0.2276(3) 0.053 Uiso 1 calc R . C29 C 0.8518(5) 0.6640(4) 0.3319(4) 0.0512(15) Uani 1 d . . H29A H 0.9051(5) 0.7128(4) 0.3739(4) 0.061 Uiso 1 calc R . C30 C 0.8007(5) 0.6494(4) 0.0787(3) 0.0421(13) Uani 1 d . . C31 C 0.9201(6) 0.6242(6) 0.0497(4) 0.077(2) Uani 1 d . . H31A H 0.9302(6) 0.6401(6) -0.0130(4) 0.116 Uiso 1 calc R . H31B H 0.9155(6) 0.5430(6) 0.0604(4) 0.116 Uiso 1 calc R . H31C H 0.9897(6) 0.6734(6) 0.0834(4) 0.116 Uiso 1 calc R . C32 C 0.6897(6) 0.5762(5) 0.0224(4) 0.069(2) Uani 1 d . . H32A H 0.6150(6) 0.5927(5) 0.0411(4) 0.103 Uiso 1 calc R . H32B H 0.6829(6) 0.4941(5) 0.0302(4) 0.103 Uiso 1 calc R . H32C H 0.7015(6) 0.5957(5) -0.0397(4) 0.103 Uiso 1 calc R . C33 C 0.8090(6) 0.7791(4) 0.0631(4) 0.067(2) Uani 1 d . . H33A H 0.7338(6) 0.7951(4) 0.0814(4) 0.100 Uiso 1 calc R . H33B H 0.8198(6) 0.7963(4) 0.0007(4) 0.100 Uiso 1 calc R . H33D H 0.8785(6) 0.8274(4) 0.0975(4) 0.100 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 Sb1 0.0228(2) 0.02368(15) 0.0270(2) -0.00009(12) 0.00150(12) 0.00930(12) Br1 0.0294(3) 0.0254(2) 0.0301(3) 0.0033(2) 0.0019(2) 0.0076(2) Br2 0.0342(3) 0.0339(3) 0.0367(3) -0.0003(2) -0.0076(2) 0.0117(2) Br3 0.0251(3) 0.0346(3) 0.0467(3) 0.0107(2) 0.0083(2) 0.0077(2) Br4 0.0404(3) 0.0374(3) 0.0285(3) -0.0070(2) -0.0028(2) 0.0120(2) N1 0.045(3) 0.057(3) 0.024(2) 0.006(2) -0.001(2) 0.024(2) N2 0.043(3) 0.039(2) 0.038(3) 0.012(2) 0.002(2) 0.000(2) N3 0.048(3) 0.041(2) 0.036(3) 0.004(2) -0.004(2) 0.002(2) C1 0.017(2) 0.019(2) 0.030(3) -0.002(2) 0.001(2) 0.005(2) C2 0.026(3) 0.030(2) 0.028(3) 0.001(2) 0.001(2) 0.007(2) C3 0.031(3) 0.034(3) 0.040(3) 0.011(2) 0.001(2) 0.017(2) C4 0.028(3) 0.033(3) 0.055(3) 0.000(2) 0.003(2) 0.018(2) C5 0.039(3) 0.037(3) 0.038(3) -0.002(2) 0.011(2) 0.018(2) C6 0.030(3) 0.026(2) 0.031(3) 0.001(2) 0.003(2) 0.011(2) C7 0.035(3) 0.054(3) 0.041(3) 0.004(3) 0.009(2) 0.020(3) C8 0.028(3) 0.043(3) 0.039(3) 0.008(2) -0.004(2) 0.014(2) C9 0.023(2) 0.025(2) 0.026(3) -0.005(2) -0.002(2) 0.006(2) C10 0.025(3) 0.041(3) 0.032(3) -0.001(2) 0.002(2) 0.015(2) C11 0.035(3) 0.054(3) 0.036(3) 0.005(2) -0.001(2) 0.023(2) C12 0.030(3) 0.032(2) 0.031(3) 0.009(2) -0.003(2) 0.007(2) C13 0.059(4) 0.043(3) 0.032(3) 0.004(2) 0.007(3) 0.017(3) C14 0.043(3) 0.038(3) 0.048(3) 0.011(3) 0.000(3) 0.012(2) C15 0.054(4) 0.057(3) 0.034(3) 0.009(3) -0.015(3) -0.005(3) C16 0.043(3) 0.049(3) 0.047(4) -0.001(3) 0.013(3) 0.017(3) C17 0.041(3) 0.032(3) 0.052(3) 0.001(2) 0.003(3) 0.017(2) C18 0.032(3) 0.025(2) 0.035(3) -0.003(2) -0.002(2) 0.009(2) C19 0.039(3) 0.033(3) 0.040(3) -0.002(2) 0.007(2) 0.013(2) C20 0.043(3) 0.024(2) 0.052(4) 0.004(2) -0.008(3) 0.010(2) C21 0.088(5) 0.040(3) 0.041(4) 0.009(3) 0.016(3) 0.018(3) C22 0.324(37) 0.164(21) 0.160(24) 0.127(19) 0.145(24) 0.217(26) C23 0.085(12) 0.184(19) 0.178(20) 0.137(17) 0.025(13) -0.020(13) C24 0.194(26) 0.074(13) 0.017(8) 0.028(8) 0.046(13) 0.018(13) C22' 0.082(13) 0.047(10) 0.065(11) 0.007(9) 0.048(9) 0.025(9) C23' 0.032(6) 0.067(7) 0.046(7) 0.038(6) -0.012(5) 0.012(5) C24' 0.059(9) 0.016(5) 0.061(9) 0.018(5) 0.015(7) 0.001(6) C25 0.034(3) 0.029(3) 0.055(4) 0.008(2) 0.009(3) 0.003(2) C26 0.038(3) 0.032(3) 0.041(3) 0.003(2) -0.006(2) 0.005(2) C27 0.036(3) 0.025(2) 0.038(3) 0.008(2) 0.003(2) 0.007(2) C28 0.041(3) 0.035(3) 0.045(3) 0.009(2) -0.003(3) -0.008(2) C29 0.055(4) 0.039(3) 0.046(4) 0.003(3) -0.015(3) -0.007(3) C30 0.051(3) 0.035(3) 0.034(3) 0.008(2) 0.006(3) 0.002(2) C31 0.083(5) 0.098(5) 0.061(4) 0.027(4) 0.033(4) 0.037(4) C32 0.102(5) 0.050(3) 0.038(4) 0.003(3) -0.010(3) -0.003(3) C33 0.102(5) 0.038(3) 0.054(4) 0.016(3) -0.009(3) 0.009(3) #======================================================================= # 10. 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 Sb1 C1 2.183(4) . ? Sb1 Br4 2.6554(11) . ? Sb1 Br3 2.7502(12) . ? Sb1 Br1 2.8493(12) . ? Sb1 Br2 2.9941(11) . ? Br1 H1A 2.743(4) 2_776 ? Br1 N1 3.372(4) 2_776 ? Br2 H1A 2.765(4) 2_776 ? Br2 N1 3.423(4) 2_776 ? N1 C11 1.315(5) . ? N1 C7 1.341(5) . ? N2 C20 1.320(6) . ? N2 C16 1.339(6) . ? N3 C25 1.322(6) . ? N3 C29 1.337(6) . ? C1 C6 1.381(6) . ? C1 C2 1.396(5) . ? C2 C3 1.386(5) . ? C3 C4 1.368(6) . ? C4 C5 1.384(6) . ? C5 C6 1.398(5) . ? C7 C8 1.370(6) . ? C8 C9 1.397(6) . ? C9 C10 1.396(5) . ? C9 C12 1.510(6) . ? C10 C11 1.377(6) . ? C12 C13 1.518(6) . ? C12 C14 1.523(6) . ? C12 C15 1.527(6) . ? C16 C17 1.367(6) . ? C17 C18 1.386(6) . ? C18 C19 1.388(5) . ? C18 C21 1.523(6) . ? C19 C20 1.370(6) . ? C21 C22 1.40(2) . ? C21 C22' 1.49(2) . ? C21 C24' 1.505(13) . ? C21 C24 1.51(2) . ? C21 C23' 1.691(11) . ? C21 C23 1.77(2) . ? C25 C26 1.389(6) . ? C26 C27 1.390(6) . ? C27 C28 1.388(6) . ? C27 C30 1.524(6) . ? C28 C29 1.361(6) . ? C30 C31 1.524(7) . ? C30 C32 1.527(7) . ? C30 C33 1.529(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 C1 Sb1 Br4 90.50(11) . . ? C1 Sb1 Br3 88.71(10) . . ? Br4 Sb1 Br3 90.87(3) . . ? C1 Sb1 Br1 89.87(10) . . ? Br4 Sb1 Br1 89.03(3) . . ? Br3 Sb1 Br1 178.57(2) . . ? C1 Sb1 Br2 88.55(11) . . ? Br4 Sb1 Br2 175.45(2) . . ? Br3 Sb1 Br2 93.55(3) . . ? Br1 Sb1 Br2 86.52(3) . . ? H1A Br1 Sb1 91.11(9) 2_776 . ? H1A Br1 N1 11.08(2) 2_776 2_776 ? Sb1 Br1 N1 102.19(7) . 2_776 ? H1A Br2 Sb1 87.70(9) 2_776 . ? H1A Br2 N1 10.34(2) 2_776 2_776 ? Sb1 Br2 N1 98.03(7) . 2_776 ? C11 N1 C7 123.0(4) . . ? C20 N2 C16 121.8(4) . . ? C25 N3 C29 116.1(4) . . ? C25 N3 H2A 111.5(3) . . ? C29 N3 H2A 132.3(4) . . ? C6 C1 C2 118.8(4) . . ? C6 C1 Sb1 121.2(3) . . ? C2 C1 Sb1 120.0(3) . . ? C3 C2 C1 120.5(4) . . ? C4 C3 C2 120.5(4) . . ? C3 C4 C5 119.9(4) . . ? C4 C5 C6 119.9(4) . . ? C1 C6 C5 120.4(4) . . ? N1 C7 C8 118.6(4) . . ? C7 C8 C9 121.9(4) . . ? C10 C9 C8 115.6(4) . . ? C10 C9 C12 123.6(4) . . ? C8 C9 C12 120.8(4) . . ? C11 C10 C9 121.3(4) . . ? N1 C11 C10 119.5(4) . . ? C9 C12 C13 111.7(4) . . ? C9 C12 C14 109.4(4) . . ? C13 C12 C14 108.9(4) . . ? C9 C12 C15 108.3(3) . . ? C13 C12 C15 108.9(4) . . ? C14 C12 C15 109.6(4) . . ? N2 C16 C17 120.2(5) . . ? C16 C17 C18 120.3(4) . . ? C17 C18 C19 116.8(4) . . ? C17 C18 C21 120.8(4) . . ? C19 C18 C21 122.4(4) . . ? C20 C19 C18 121.2(5) . . ? N2 C20 C19 119.7(4) . . ? C22' C21 C24' 111.4(9) . . ? C22 C21 C24 128.5(13) . . ? C22 C21 C18 119.0(10) . . ? C22' C21 C18 120.6(8) . . ? C24' C21 C18 107.9(7) . . ? C24 C21 C18 108.8(7) . . ? C22' C21 C23' 106.3(11) . . ? C24' C21 C23' 106.5(7) . . ? C18 C21 C23' 102.9(5) . . ? C22 C21 C23 98.3(14) . . ? C24 C21 C23 91.6(12) . . ? C18 C21 C23 99.2(6) . . ? N3 C25 C26 123.7(4) . . ? C25 C26 C27 119.7(5) . . ? C28 C27 C26 115.9(4) . . ? C28 C27 C30 122.7(4) . . ? C26 C27 C30 121.4(4) . . ? C29 C28 C27 120.3(4) . . ? N3 C29 C28 124.2(5) . . ? C31 C30 C27 107.7(4) . . ? C31 C30 C32 110.1(5) . . ? C27 C30 C32 112.4(4) . . ? C31 C30 C33 109.5(4) . . ? C27 C30 C33 109.6(4) . . ? C32 C30 C33 107.6(4) . . ? _refine_diff_density_max 0.929 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.109 ##end##