# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sad _audit_creation_date 2013-06-12T08:50:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H17 Bi Cl4 N4 O2' _chemical_formula_weight 696.16 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' 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 23.6950(10) _cell_length_b 26.6618(10) _cell_length_c 7.2913(5) _cell_angle_alpha 90 _cell_angle_beta 95.950(10) _cell_angle_gamma 90 _cell_volume 4581.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 2.019 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.283 _exptl_absorpt_correction_T_max 0.446 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0801 _diffrn_reflns_av_unetI/netI 0.0579 _diffrn_reflns_number 67247 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.7 _diffrn_reflns_theta_max 32.08 _diffrn_reflns_theta_full 32.08 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 7990 _reflns_number_gt 4253 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+16.1052P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7990 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0554 _refine_ls_wR_factor_gt 0.0441 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.877 _refine_diff_density_min -0.951 _refine_diff_density_rms 0.138 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.29177(19) 0.23864(16) 1.3350(6) 0.0361(10) Uani 1 1 d . . . H1 H 0.3102 0.2086 1.3675 0.043 Uiso 1 1 calc R . . C2 C 0.24013(16) 0.23776(15) 1.2327(6) 0.0315(11) Uani 1 1 d . . . H033 H 0.2239 0.207 1.198 0.038 Uiso 1 1 calc R . . C3 C 0.21103(17) 0.28159(15) 1.1787(5) 0.0287(9) Uani 1 1 d . . . C4 C 0.23803(16) 0.32592(16) 1.2372(6) 0.0364(11) Uani 1 1 d . . . H018 H 0.2204 0.3563 1.2057 0.044 Uiso 1 1 calc R . . C5 C 0.2895(2) 0.32610(17) 1.3391(7) 0.0440(11) Uani 1 1 d . . . H022 H 0.3065 0.3565 1.3748 0.053 Uiso 1 1 calc R . . C6 C 0.15592(19) 0.28110(16) 1.0654(6) 0.0293(9) Uani 1 1 d . . . C7 C 0.13033(17) 0.32472(17) 0.9957(6) 0.0380(10) Uani 1 1 d . . . H016 H 0.148 0.3554 1.0218 0.046 Uiso 1 1 calc R . . C8 C 0.07874(18) 0.32327(17) 0.8877(6) 0.0405(10) Uani 1 1 d . . . H013 H 0.0621 0.3531 0.8437 0.049 Uiso 1 1 calc R . . C9 C 0.07626(18) 0.23719(18) 0.9090(6) 0.0424(11) Uani 1 1 d . . . H030 H 0.0581 0.207 0.8785 0.051 Uiso 1 1 calc R . . C10 C 0.12733(18) 0.23693(17) 1.0189(6) 0.0398(10) Uani 1 1 d . . . H021 H 0.1428 0.2066 1.0624 0.048 Uiso 1 1 calc R . . C11 C 0.54110(18) 0.20116(16) 0.8483(6) 0.0406(11) Uani 1 1 d . . . H028 H 0.5701 0.2187 0.9162 0.049 Uiso 1 1 calc R . . C12 C 0.54258(17) 0.14954(17) 0.8538(6) 0.0376(10) Uani 1 1 d . . . H024 H 0.5714 0.1327 0.9254 0.045 Uiso 1 1 calc R . . C13 C 0.5 0.1232(3) 0.75 0.0315(14) Uani 1 2 d S . . C14 C 0.5 0.0674(2) 0.75 0.0321(13) Uani 1 2 d S . . C15 C 0.4506(2) 0.0399(2) 0.7190(7) 0.0505(13) Uani 1 1 d . . . H031 H 0.4162 0.0567 0.6966 0.061 Uiso 1 1 calc R . . C16 C 0.4509(2) -0.0113(2) 0.7204(8) 0.0546(14) Uani 1 1 d . . . H034 H 0.4168 -0.0288 0.7007 0.066 Uiso 1 1 calc R . . C17 C 0.4539(2) 0.3560(2) 0.6887(7) 0.0546(14) Uani 1 1 d . . . H020 H 0.4215 0.3383 0.6441 0.065 Uiso 1 1 calc R . . C18 C 0.45208(18) 0.40705(18) 0.6886(7) 0.0464(12) Uani 1 1 d . . . H029 H 0.4184 0.4233 0.647 0.056 Uiso 1 1 calc R . . C19 C 0.5 0.4355(3) 0.75 0.0337(15) Uani 1 2 d S . . C20 C 0.5 0.4896(3) 0.75 0.0343(14) Uani 1 2 d S . . C21 C 0.5499(2) 0.5185(2) 0.7829(7) 0.0497(14) Uani 1 1 d . . . H035 H 0.5846 0.5022 0.8043 0.06 Uiso 1 1 calc R . . C22 C 0.5489(2) 0.5688(2) 0.7843(7) 0.0518(13) Uani 1 1 d . . . H039 H 0.5828 0.5862 0.8097 0.062 Uiso 1 1 calc R . . N1 N 0.31628(17) 0.28250(15) 1.3894(5) 0.0393(9) Uani 1 1 d . . . N2 N 0.05252(14) 0.27993(15) 0.8456(5) 0.0400(9) Uani 1 1 d . . . H2 H 0.0205 0.2796 0.778 0.048 Uiso 0.5 1 calc PR . . N3 N 0.5 0.22755(19) 0.75 0.0381(12) Uani 1 2 d S . . N4 N 0.5 -0.0366(2) 0.75 0.0444(14) Uani 1 2 d S . . N5 N 0.5 0.3305(2) 0.75 0.0427(13) Uani 1 2 d S . . H5 H 0.5 0.2983 0.75 0.051 Uiso 1 2 calc SR . . N6 N 0.5 0.5952(3) 0.75 0.0519(16) Uani 1 2 d S . . O1 O 0.36549(14) 0.28278(14) 1.4880(5) 0.0607(10) Uani 1 1 d . . . O2 O 0.5 -0.08567(19) 0.75 0.0705(17) Uani 1 2 d S . . O3 O 0.5 0.6423(2) 0.75 0.082(2) Uani 1 2 d S . . Cl1 Cl 0.18631(5) 0.45991(5) 1.04498(16) 0.0424(3) Uani 1 1 d . . . Cl2 Cl 0.31649(6) 0.39330(5) 0.90306(19) 0.0522(4) Uani 1 1 d . . . Cl3 Cl 0.31466(5) 0.46197(5) 0.46428(16) 0.0412(3) Uani 1 1 d . . . Cl4 Cl 0.18048(6) 0.39554(5) 0.59737(19) 0.0516(4) Uani 1 1 d . . . Bi1 Bi 0.249462(9) 0.458606(5) 0.75416(3) 0.02718(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.039(2) 0.028(2) 0.041(2) 0.0010(19) 0.000(2) 0.0092(19) C2 0.035(3) 0.025(2) 0.034(2) -0.0052(19) 0.001(2) -0.0019(17) C3 0.032(2) 0.026(2) 0.029(2) 0.0007(17) 0.0082(17) 0.0028(18) C4 0.038(3) 0.022(2) 0.047(3) 0.000(2) -0.001(3) 0.0002(17) C5 0.045(3) 0.028(3) 0.056(3) 0.003(2) -0.010(2) 0.000(2) C6 0.032(2) 0.027(2) 0.030(2) -0.0003(18) 0.0094(18) 0.002(2) C7 0.038(2) 0.032(2) 0.042(2) 0.004(2) -0.004(2) -0.0016(19) C8 0.042(3) 0.033(3) 0.045(3) 0.004(2) -0.004(2) 0.005(2) C9 0.040(2) 0.034(3) 0.052(3) -0.001(2) 0.000(2) -0.002(2) C10 0.039(2) 0.029(2) 0.050(3) -0.001(2) -0.003(2) 0.0038(19) C11 0.040(2) 0.030(3) 0.050(3) -0.005(2) -0.001(2) -0.0045(19) C12 0.032(2) 0.036(3) 0.044(3) 0.000(2) -0.0035(19) 0.0025(19) C13 0.028(3) 0.034(4) 0.033(3) 0 0.008(2) 0 C14 0.027(3) 0.035(4) 0.033(3) 0 0.000(2) 0 C15 0.030(2) 0.042(3) 0.077(4) 0.007(3) -0.003(2) -0.002(3) C16 0.034(3) 0.042(3) 0.085(4) 0.003(3) -0.010(3) -0.004(2) C17 0.043(3) 0.042(3) 0.076(4) -0.002(3) -0.010(3) -0.009(2) C18 0.028(2) 0.041(3) 0.068(3) 0.004(2) -0.008(2) 0.002(2) C19 0.024(3) 0.041(4) 0.036(3) 0 -0.003(2) 0 C20 0.030(3) 0.040(4) 0.032(3) 0 0.002(3) 0 C21 0.031(3) 0.054(4) 0.062(3) 0.005(3) -0.006(2) 0.000(3) C22 0.035(3) 0.044(3) 0.074(4) 0.003(3) -0.005(3) -0.009(3) N1 0.034(2) 0.040(2) 0.042(2) -0.0033(19) -0.0018(17) -0.001(2) N2 0.0320(19) 0.049(3) 0.038(2) 0.0020(18) -0.0041(16) 0.0021(17) N3 0.042(3) 0.029(3) 0.043(3) 0 0.007(2) 0 N4 0.045(3) 0.027(3) 0.058(3) 0 -0.012(3) 0 N5 0.048(3) 0.028(3) 0.051(3) 0 -0.002(3) 0 N6 0.057(4) 0.039(4) 0.058(4) 0 -0.003(3) 0 O1 0.043(2) 0.052(3) 0.081(3) -0.002(2) -0.0225(19) 0.0012(18) O2 0.065(4) 0.025(3) 0.116(5) 0 -0.021(3) 0 O3 0.085(4) 0.036(4) 0.121(5) 0 -0.005(4) 0 Cl1 0.0379(7) 0.0413(8) 0.0487(7) -0.0066(7) 0.0090(6) -0.0099(7) Cl2 0.0503(8) 0.0381(9) 0.0664(9) 0.0138(7) -0.0029(7) 0.0122(7) Cl3 0.0339(7) 0.0418(8) 0.0483(7) 0.0056(6) 0.0056(6) 0.0103(6) Cl4 0.0485(8) 0.0416(9) 0.0622(9) -0.0104(7) -0.0052(7) -0.0138(7) Bi1 0.02659(6) 0.02221(6) 0.03202(7) 0.00021(11) -0.00043(4) -0.00069(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.347(5) . ? C1 C2 1.366(6) . ? C2 C3 1.393(5) . ? C3 C4 1.390(5) . ? C3 C6 1.471(6) . ? C4 C5 1.360(6) . ? C5 N1 1.357(5) . ? C6 C10 1.383(6) . ? C6 C7 1.384(6) . ? C7 C8 1.385(6) . ? C8 N2 1.333(5) . ? C9 N2 1.332(5) . ? C9 C10 1.381(6) . ? C11 N3 1.346(5) . ? C11 C12 1.377(6) . ? C12 C13 1.388(5) . ? C13 C12 1.388(5) 2_656 ? C13 C14 1.488(9) . ? C14 C15 1.380(6) . ? C14 C15 1.380(6) 2_656 ? C15 C16 1.366(7) . ? C16 N4 1.343(6) . ? C17 N5 1.325(5) . ? C17 C18 1.362(6) . ? C18 C19 1.400(6) . ? C19 C18 1.400(6) 2_656 ? C19 C20 1.441(9) . ? C20 C21 1.411(6) 2_656 ? C20 C21 1.411(6) . ? C21 C22 1.342(7) . ? C22 N6 1.356(6) . ? N1 O1 1.305(5) . ? N3 C11 1.346(5) 2_656 ? N4 O2 1.307(7) . ? N4 C16 1.343(6) 2_656 ? N5 C17 1.325(5) 2_656 ? N6 O3 1.255(7) . ? N6 C22 1.356(6) 2_656 ? Cl1 Bi1 2.7193(11) . ? Cl1 Bi1 2.9685(13) 6_566 ? Cl2 Bi1 2.5249(13) . ? Cl3 Bi1 2.7457(11) . ? Cl3 Bi1 2.9542(13) 6_565 ? Cl4 Bi1 2.5335(13) . ? Bi1 Cl3 2.9542(13) 6_566 ? Bi1 Cl1 2.9685(13) 6_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 120.7(4) . . ? C1 C2 C3 122.0(4) . . ? C4 C3 C2 115.3(4) . . ? C4 C3 C6 122.2(4) . . ? C2 C3 C6 122.4(4) . . ? C5 C4 C3 121.9(4) . . ? N1 C5 C4 120.8(4) . . ? C10 C6 C7 116.1(4) . . ? C10 C6 C3 121.9(4) . . ? C7 C6 C3 121.9(4) . . ? C6 C7 C8 120.9(4) . . ? N2 C8 C7 121.2(4) . . ? N2 C9 C10 121.3(4) . . ? C9 C10 C6 121.0(4) . . ? N3 C11 C12 123.5(4) . . ? C11 C12 C13 118.4(5) . . ? C12 C13 C12 119.2(6) 2_656 . ? C12 C13 C14 120.4(3) 2_656 . ? C12 C13 C14 120.4(3) . . ? C15 C14 C15 115.9(7) . 2_656 ? C15 C14 C13 122.1(3) . . ? C15 C14 C13 122.1(3) 2_656 . ? C16 C15 C14 121.7(5) . . ? N4 C16 C15 120.5(5) . . ? N5 C17 C18 122.5(5) . . ? C17 C18 C19 121.1(5) . . ? C18 C19 C18 114.4(7) . 2_656 ? C18 C19 C20 122.8(3) . . ? C18 C19 C20 122.8(3) 2_656 . ? C21 C20 C21 113.6(7) 2_656 . ? C21 C20 C19 123.2(3) 2_656 . ? C21 C20 C19 123.2(3) . . ? C22 C21 C20 122.3(5) . . ? C21 C22 N6 122.2(5) . . ? O1 N1 C1 120.0(4) . . ? O1 N1 C5 120.7(4) . . ? C1 N1 C5 119.3(4) . . ? C9 N2 C8 119.5(4) . . ? C11 N3 C11 117.0(5) 2_656 . ? O2 N4 C16 120.1(3) . 2_656 ? O2 N4 C16 120.1(3) . . ? C16 N4 C16 119.7(7) 2_656 . ? C17 N5 C17 118.3(6) 2_656 . ? O3 N6 C22 121.3(3) . 2_656 ? O3 N6 C22 121.3(3) . . ? C22 N6 C22 117.5(7) 2_656 . ? Bi1 Cl1 Bi1 96.96(4) . 6_566 ? Bi1 Cl3 Bi1 96.71(3) . 6_565 ? Cl2 Bi1 Cl4 94.82(4) . . ? Cl2 Bi1 Cl1 92.63(4) . . ? Cl4 Bi1 Cl1 88.79(4) . . ? Cl2 Bi1 Cl3 88.54(4) . . ? Cl4 Bi1 Cl3 93.58(4) . . ? Cl1 Bi1 Cl3 177.26(3) . . ? Cl2 Bi1 Cl3 89.97(5) . 6_566 ? Cl4 Bi1 Cl3 171.12(4) . 6_566 ? Cl1 Bi1 Cl3 83.51(3) . 6_566 ? Cl3 Bi1 Cl3 94.02(3) . 6_566 ? Cl2 Bi1 Cl1 170.65(4) . 6_565 ? Cl4 Bi1 Cl1 89.24(5) . 6_565 ? Cl1 Bi1 Cl1 95.88(3) . 6_565 ? Cl3 Bi1 Cl1 82.79(3) . 6_565 ? Cl3 Bi1 Cl1 87.16(3) 6_566 6_565 ? _database_code_depnum_ccdc_archive 'CCDC 952307' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sad _audit_creation_date 2013-02-20T14:46:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C10 H9 Bi Cl4 N2 O' _chemical_formula_weight 523.97 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' 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 18.8244(8) _cell_length_b 9.7773(2) _cell_length_c 16.5190(7) _cell_angle_alpha 90 _cell_angle_beta 94.968(5) _cell_angle_gamma 90 _cell_volume 3028.93(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 2.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 12.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.114 _exptl_absorpt_correction_T_max 0.319 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_unetI/netI 0.0929 _diffrn_reflns_number 22424 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.98 _diffrn_reflns_theta_max 32.01 _diffrn_reflns_theta_full 32.01 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 5215 _reflns_number_gt 2962 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0154P)^2^+2.7411P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5215 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1204 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.0626 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.108 _refine_diff_density_min -0.82 _refine_diff_density_rms 0.197 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.815566(10) 0.109688(19) 0.066893(11) 0.03303(6) Uani 1 1 d . . . Cl4 Cl 0.94656(7) 0.15750(17) 0.12071(10) 0.0628(4) Uani 1 1 d . . . Cl2 Cl 0.85395(8) -0.05569(16) -0.05427(8) 0.0523(4) Uani 1 1 d . . . Cl1 Cl 0.67168(7) 0.11630(15) 0.00509(8) 0.0478(3) Uani 1 1 d . . . Cl3 Cl 0.81210(9) -0.10033(17) 0.15712(10) 0.0732(5) Uani 1 1 d . . . N1 N 0.8117(2) 0.3233(5) 0.2155(2) 0.0367(10) Uani 1 1 d . . . O1 O 0.76853(18) 0.2355(4) 0.1723(2) 0.0476(9) Uani 1 1 d . . . C6 C 0.9492(3) 0.6018(5) 0.3473(3) 0.0361(11) Uani 1 1 d . . . C1 C 0.8579(3) 0.2773(5) 0.2753(3) 0.0469(14) Uani 1 1 d . . . H1 H 0.86 0.1843 0.2872 0.056 Uiso 1 1 calc R . . N2 N 1.0394(3) 0.7793(6) 0.4317(3) 0.0608(15) Uani 1 1 d . . . C4 C 0.8058(3) 0.4582(6) 0.1988(3) 0.0415(13) Uani 1 1 d . . . H4 H 0.7722 0.4889 0.1583 0.05 Uiso 1 1 calc R . . C3 C 0.8999(3) 0.5053(5) 0.3026(3) 0.0324(11) Uani 1 1 d . . . C7 C 1.0118(3) 0.5580(6) 0.3899(3) 0.0486(14) Uani 1 1 d . . . H7 H 1.0234 0.4656 0.3896 0.058 Uiso 1 1 calc R . . C8 C 1.0561(3) 0.6464(7) 0.4318(4) 0.0557(16) Uani 1 1 d . . . H8 H 1.0978 0.6153 0.4603 0.067 Uiso 1 1 calc R . . C5 C 0.8494(3) 0.5496(5) 0.2418(3) 0.0385(12) Uani 1 1 d . . . H5 H 0.8453 0.6425 0.2301 0.046 Uiso 1 1 calc R . . C9 C 0.9349(3) 0.7413(6) 0.3500(4) 0.0538(15) Uani 1 1 d . . . H9 H 0.8937 0.7758 0.3222 0.065 Uiso 1 1 calc R . . C2 C 0.9019(3) 0.3661(5) 0.3187(3) 0.0439(14) Uani 1 1 d . . . H2 H 0.934 0.3327 0.36 0.053 Uiso 1 1 calc R . . C10 C 0.9806(4) 0.8276(6) 0.3929(4) 0.0652(19) Uani 1 1 d . . . H10 H 0.9703 0.9205 0.3949 0.078 Uiso 1 1 calc R . . H3 H 1.069(3) 0.837(6) 0.461(4) 0.07(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.03380(10) 0.02881(10) 0.03653(11) -0.00091(10) 0.00334(7) 0.00232(10) Cl4 0.0402(8) 0.0599(10) 0.0858(12) -0.0107(9) -0.0085(8) 0.0007(7) Cl2 0.0561(9) 0.0556(9) 0.0442(8) -0.0100(7) -0.0013(7) 0.0115(7) Cl1 0.0393(7) 0.0496(8) 0.0548(8) 0.0036(7) 0.0051(6) -0.0062(7) Cl3 0.0864(12) 0.0582(10) 0.0805(11) 0.0329(9) 0.0399(10) 0.0204(9) N1 0.036(2) 0.036(3) 0.040(3) -0.007(2) 0.009(2) -0.004(2) O1 0.045(2) 0.046(2) 0.052(2) -0.0166(19) 0.0071(18) -0.0107(19) C6 0.036(3) 0.032(3) 0.042(3) -0.003(3) 0.011(2) 0.003(3) C1 0.066(4) 0.028(3) 0.046(3) 0.003(3) -0.001(3) 0.002(3) N2 0.047(3) 0.060(4) 0.077(4) -0.023(3) 0.014(3) -0.014(3) C4 0.040(3) 0.040(3) 0.044(3) -0.001(3) -0.001(3) 0.011(3) C3 0.039(3) 0.025(3) 0.034(3) -0.001(2) 0.008(2) 0.003(2) C7 0.046(3) 0.040(3) 0.059(4) -0.004(3) 0.002(3) 0.002(3) C8 0.044(3) 0.059(5) 0.063(4) -0.006(3) -0.001(3) -0.003(3) C5 0.045(3) 0.027(3) 0.043(3) -0.002(2) 0.005(3) 0.006(2) C9 0.052(4) 0.033(3) 0.075(4) -0.007(3) -0.002(3) 0.003(3) C2 0.056(3) 0.035(4) 0.038(3) 0.002(2) -0.007(3) 0.000(3) C10 0.062(4) 0.034(3) 0.101(5) -0.025(4) 0.018(4) -0.009(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O1 2.365(3) . ? Bi1 Cl3 2.5415(14) . ? Bi1 Cl4 2.5904(14) . ? Bi1 Cl2 2.7191(13) . ? Bi1 Cl1 2.8114(13) . ? Bi1 Cl1 2.9493(14) 7_655 ? Cl1 Bi1 2.9493(14) 7_655 ? N1 C1 1.336(6) . ? N1 O1 1.345(5) . ? N1 C4 1.350(6) . ? C6 C7 1.387(7) . ? C6 C9 1.391(7) . ? C6 C3 1.476(7) . ? C1 C2 1.360(7) . ? C1 H1 0.93 . ? N2 C10 1.318(8) . ? N2 C8 1.337(7) . ? N2 H3 0.91(6) . ? C4 C5 1.370(7) . ? C4 H4 0.93 . ? C3 C2 1.387(6) . ? C3 C5 1.391(7) . ? C7 C8 1.350(7) . ? C7 H7 0.93 . ? C8 H8 0.93 . ? C5 H5 0.93 . ? C9 C10 1.359(8) . ? C9 H9 0.93 . ? C2 H2 0.93 . ? C10 H10 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Bi1 Cl3 87.62(10) . . ? O1 Bi1 Cl4 93.41(9) . . ? Cl3 Bi1 Cl4 90.95(6) . . ? O1 Bi1 Cl2 172.45(9) . . ? Cl3 Bi1 Cl2 88.46(5) . . ? Cl4 Bi1 Cl2 93.11(5) . . ? O1 Bi1 Cl1 81.08(9) . . ? Cl3 Bi1 Cl1 99.13(5) . . ? Cl4 Bi1 Cl1 168.25(5) . . ? Cl2 Bi1 Cl1 93.18(4) . . ? O1 Bi1 Cl1 82.70(9) . 7_655 ? Cl3 Bi1 Cl1 167.82(5) . 7_655 ? Cl4 Bi1 Cl1 82.31(4) . 7_655 ? Cl2 Bi1 Cl1 101.96(4) . 7_655 ? Cl1 Bi1 Cl1 86.69(4) . 7_655 ? Bi1 Cl1 Bi1 93.31(4) . 7_655 ? C1 N1 O1 120.2(4) . . ? C1 N1 C4 121.2(5) . . ? O1 N1 C4 118.6(4) . . ? N1 O1 Bi1 118.4(2) . . ? C7 C6 C9 116.4(5) . . ? C7 C6 C3 121.7(5) . . ? C9 C6 C3 121.9(5) . . ? N1 C1 C2 120.1(5) . . ? N1 C1 H1 120 . . ? C2 C1 H1 120 . . ? C10 N2 C8 122.5(6) . . ? C10 N2 H3 119(4) . . ? C8 N2 H3 118(4) . . ? N1 C4 C5 119.8(5) . . ? N1 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C2 C3 C5 116.7(5) . . ? C2 C3 C6 121.8(5) . . ? C5 C3 C6 121.5(4) . . ? C8 C7 C6 121.5(6) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? N2 C8 C7 119.1(6) . . ? N2 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C4 C5 C3 120.8(5) . . ? C4 C5 H5 119.6 . . ? C3 C5 H5 119.6 . . ? C10 C9 C6 120.7(6) . . ? C10 C9 H9 119.6 . . ? C6 C9 H9 119.6 . . ? C1 C2 C3 121.4(5) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? N2 C10 C9 119.8(6) . . ? N2 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? _database_code_depnum_ccdc_archive 'CCDC 952308' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sad _audit_creation_date 2013-02-20T11:53:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H18 Bi2 Br8 N4 O2' _chemical_formula_weight 1403.62 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1031(6) _cell_length_b 12.8928(5) _cell_length_c 12.5741(10) _cell_angle_alpha 90 _cell_angle_beta 104.077(6) _cell_angle_gamma 90 _cell_volume 1588.68(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 2.934 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 21.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.078 _exptl_absorpt_correction_T_max 0.133 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_av_unetI/netI 0.0633 _diffrn_reflns_number 22302 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 30 _diffrn_reflns_theta_full 30 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 4610 _reflns_number_gt 3225 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0133P)^2^+1.6465P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4610 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0509 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.05 _refine_diff_density_min -1.097 _refine_diff_density_rms 0.219 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.38799(2) 0.938027(14) 0.108959(17) 0.02491(6) Uani 1 1 d . . . Br4 Br 0.36970(5) 0.91460(4) -0.12762(5) 0.03462(14) Uani 1 1 d . . . Br1 Br 0.57707(6) 0.77043(4) 0.16193(5) 0.04081(16) Uani 1 1 d . . . Br3 Br 0.21940(6) 1.11445(4) 0.06690(5) 0.04173(16) Uani 1 1 d . . . Br2 Br 0.17243(7) 0.81531(5) 0.10855(7) 0.0599(2) Uani 1 1 d . . . C3 C 0.7651(5) 1.0273(4) 0.5228(4) 0.0257(12) Uani 1 1 d . . . N1 N 0.5302(4) 0.9866(3) 0.3648(4) 0.0288(10) Uani 1 1 d . . . O1 O 0.4089(4) 0.9680(3) 0.2957(3) 0.0395(10) Uani 1 1 d . . . N2 N 1.1012(5) 1.0831(4) 0.7888(5) 0.0408(13) Uani 1 1 d . . . C10 C 1.0732(6) 1.1514(4) 0.7065(5) 0.0422(16) Uani 1 1 d . . . H10 H 1.1277 1.2098 0.7087 0.051 Uiso 1 1 calc R . . C8 C 0.5255(6) 0.5024(4) 0.2896(5) 0.0399(15) Uani 1 1 d . . . H8 H 0.5463 0.5479 0.3486 0.048 Uiso 1 1 calc R . . C7 C 0.4174(5) 0.5216(4) 0.2024(5) 0.0294(13) Uani 1 1 d . . . H7 H 0.3656 0.5814 0.2017 0.035 Uiso 1 1 calc R . . C6 C 0.8845(5) 1.0469(4) 0.6152(5) 0.0280(12) Uani 1 1 d . . . C4 C 0.5667(6) 1.0858(4) 0.3902(5) 0.0331(13) Uani 1 1 d . . . H4 H 0.5125 1.1397 0.3545 0.04 Uiso 1 1 calc R . . C9 C 0.9656(6) 1.1357(4) 0.6199(5) 0.0369(14) Uani 1 1 d . . . H9 H 0.9454 1.184 0.5634 0.044 Uiso 1 1 calc R . . C1 C 0.6101(6) 0.9070(4) 0.4123(5) 0.0348(14) Uani 1 1 d . . . H1 H 0.5854 0.8391 0.3916 0.042 Uiso 1 1 calc R . . C5 C 0.6833(6) 1.1072(4) 0.4684(5) 0.0323(13) Uani 1 1 d . . . H5 H 0.7083 1.1758 0.4854 0.039 Uiso 1 1 calc R . . C2 C 0.7256(6) 0.9262(4) 0.4898(5) 0.0327(13) Uani 1 1 d . . . H2 H 0.7801 0.8709 0.522 0.039 Uiso 1 1 calc R . . H3 H 1.166(6) 1.102(4) 0.845(5) 0.05(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02585(10) 0.02632(10) 0.02060(11) -0.00131(9) 0.00185(8) -0.00162(9) Br4 0.0342(3) 0.0389(3) 0.0282(3) -0.0084(3) 0.0029(3) -0.0021(2) Br1 0.0412(3) 0.0389(3) 0.0398(4) 0.0029(3) 0.0049(3) 0.0089(3) Br3 0.0487(4) 0.0362(3) 0.0403(4) 0.0077(3) 0.0109(3) 0.0095(3) Br2 0.0462(4) 0.0390(3) 0.1032(7) -0.0240(4) 0.0349(4) -0.0154(3) C3 0.033(3) 0.026(3) 0.020(3) 0.000(2) 0.008(3) -0.002(2) N1 0.024(2) 0.043(3) 0.018(3) -0.004(2) 0.002(2) 0.000(2) O1 0.028(2) 0.068(3) 0.020(2) -0.007(2) 0.0020(19) -0.0002(19) N2 0.028(3) 0.048(3) 0.034(3) -0.001(3) -0.016(2) 0.003(2) C10 0.034(3) 0.039(3) 0.046(5) 0.004(3) -0.006(3) -0.004(3) C8 0.037(4) 0.036(3) 0.043(4) -0.010(3) 0.002(3) -0.008(3) C7 0.025(3) 0.032(3) 0.028(3) -0.006(3) 0.000(3) 0.000(2) C6 0.028(3) 0.030(3) 0.027(3) -0.002(3) 0.008(2) 0.002(2) C4 0.040(3) 0.031(3) 0.028(3) 0.003(3) 0.006(3) 0.009(2) C9 0.035(3) 0.031(3) 0.041(4) 0.010(3) 0.002(3) -0.005(2) C1 0.048(4) 0.026(3) 0.029(4) 0.000(2) 0.007(3) -0.002(3) C5 0.043(3) 0.027(3) 0.027(3) -0.001(3) 0.007(3) -0.005(3) C2 0.039(3) 0.032(3) 0.023(3) 0.001(3) 0.000(3) 0.004(2) #----------------------------------------------------------------------------# # 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 O1 2.338(4) . ? Bi1 Br2 2.6909(6) . ? Bi1 Br3 2.8136(6) . ? Bi1 Br1 2.8536(6) . ? Bi1 Br4 2.9509(7) . ? Bi1 Br4 3.0625(6) 3_675 ? Br4 Bi1 3.0625(6) 3_675 ? C3 C5 1.391(7) . ? C3 C2 1.397(7) . ? C3 C6 1.480(7) . ? N1 O1 1.340(5) . ? N1 C4 1.347(6) . ? N1 C1 1.352(7) . ? N2 C10 1.335(7) . ? N2 C8 1.342(7) 4_676 ? N2 H3 0.87(6) . ? C10 C9 1.353(8) . ? C10 H10 0.93 . ? C8 N2 1.342(7) 4_575 ? C8 C7 1.369(8) . ? C8 H8 0.93 . ? C7 C6 1.384(7) 4_575 ? C7 H7 0.93 . ? C6 C7 1.384(7) 4_676 ? C6 C9 1.400(7) . ? C4 C5 1.367(7) . ? C4 H4 0.93 . ? C9 H9 0.93 . ? C1 C2 1.350(7) . ? C1 H1 0.93 . ? C5 H5 0.93 . ? C2 H2 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Bi1 Br2 88.54(9) . . ? O1 Bi1 Br3 87.58(9) . . ? Br2 Bi1 Br3 91.28(2) . . ? O1 Bi1 Br1 89.94(9) . . ? Br2 Bi1 Br1 92.91(2) . . ? Br3 Bi1 Br1 175.080(19) . . ? O1 Bi1 Br4 176.03(10) . . ? Br2 Bi1 Br4 94.91(2) . . ? Br3 Bi1 Br4 90.381(18) . . ? Br1 Bi1 Br4 91.835(18) . . ? O1 Bi1 Br4 86.85(9) . 3_675 ? Br2 Bi1 Br4 175.17(2) . 3_675 ? Br3 Bi1 Br4 87.073(17) . 3_675 ? Br1 Bi1 Br4 88.549(17) . 3_675 ? Br4 Bi1 Br4 89.638(17) . 3_675 ? Bi1 Br4 Bi1 90.362(17) . 3_675 ? C5 C3 C2 116.9(5) . . ? C5 C3 C6 122.2(5) . . ? C2 C3 C6 120.8(5) . . ? O1 N1 C4 118.6(5) . . ? O1 N1 C1 120.3(5) . . ? C4 N1 C1 121.1(5) . . ? N1 O1 Bi1 121.7(3) . . ? C10 N2 C8 122.2(6) . 4_676 ? C10 N2 H3 115(4) . . ? C8 N2 H3 122(4) 4_676 . ? N2 C10 C9 120.1(6) . . ? N2 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N2 C8 C7 119.2(6) 4_575 . ? N2 C8 H8 120.4 4_575 . ? C7 C8 H8 120.4 . . ? C8 C7 C6 120.6(5) . 4_575 ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 4_575 . ? C7 C6 C9 117.6(5) 4_676 . ? C7 C6 C3 120.4(5) 4_676 . ? C9 C6 C3 122.0(5) . . ? N1 C4 C5 120.0(5) . . ? N1 C4 H4 120 . . ? C5 C4 H4 120 . . ? C10 C9 C6 120.2(5) . . ? C10 C9 H9 119.9 . . ? C6 C9 H9 119.9 . . ? C2 C1 N1 119.9(5) . . ? C2 C1 H1 120 . . ? N1 C1 H1 120 . . ? C4 C5 C3 120.6(5) . . ? C4 C5 H5 119.7 . . ? C3 C5 H5 119.7 . . ? C1 C2 C3 121.3(5) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? _database_code_depnum_ccdc_archive 'CCDC 952309' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sad _audit_creation_date 2013-04-16T11:13:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H9 Bi Br4 N2 O' _chemical_formula_sum 'C10 H9 Bi Br4 N2 O' _chemical_formula_weight 701.81 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.4049(8) _cell_length_b 21.2014(18) _cell_length_c 9.3965(6) _cell_angle_alpha 90 _cell_angle_beta 107.241(5) _cell_angle_gamma 90 _cell_volume 1599.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7233 _cell_measurement_theta_min 2 _cell_measurement_theta_max 32.05 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 2.915 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 21.009 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS (Sheldrick, Bruker, 2008))' _exptl_absorpt_correction_T_min 0.0338 _exptl_absorpt_correction_T_max 0.3654 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.1097 _diffrn_reflns_av_unetI/netI 0.1187 _diffrn_reflns_number 30390 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 32.05 _diffrn_reflns_theta_full 32.05 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 5525 _reflns_number_gt 3082 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2i (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.7399P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5525 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1326 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.291 _refine_diff_density_min -1.732 _refine_diff_density_rms 0.305 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.51179(4) 0.347755(15) 1.23301(3) 0.02709(10) Uani 1 1 d . . . Br2 Br 0.62973(11) 0.39629(5) 1.52894(9) 0.0379(2) Uani 1 1 d . . . Br1 Br 0.30304(12) 0.44941(5) 1.15403(10) 0.0396(2) Uani 1 1 d . . . Br4 Br 0.73549(13) 0.40588(5) 1.12226(12) 0.0470(3) Uani 1 1 d . . . Br3 Br 0.74271(11) 0.23611(5) 1.30326(12) 0.0458(3) Uani 1 1 d . . . O1 O 0.3830(7) 0.3146(3) 0.9837(6) 0.0407(16) Uani 1 1 d . . . N2 N 0.7178(11) 0.0464(4) 0.5019(10) 0.044(2) Uani 1 1 d . . . N1 N 0.4438(8) 0.2691(3) 0.9109(7) 0.0297(16) Uani 1 1 d . . . C3 C 0.4974(10) 0.2862(4) 0.7951(9) 0.035(2) Uani 1 1 d . . . H3 H 0.5031 0.3287 0.7722 0.042 Uiso 1 1 calc R . . C10 C 0.6159(12) 0.0910(5) 0.4290(11) 0.048(3) Uani 1 1 d . . . H10 H 0.5856 0.0932 0.3256 0.057 Uiso 1 1 calc R . . C6 C 0.5978(9) 0.1302(4) 0.6629(9) 0.0271(18) Uani 1 1 d . . . C9 C 0.5557(10) 0.1341(5) 0.5102(10) 0.037(2) Uani 1 1 d . . . H9 H 0.4856 0.1663 0.461 0.045 Uiso 1 1 calc R . . C4 C 0.5441(9) 0.2406(4) 0.7099(9) 0.031(2) Uani 1 1 d . . . H4 H 0.5771 0.2521 0.6274 0.037 Uiso 1 1 calc R . . C2 C 0.4873(10) 0.1623(4) 0.8703(9) 0.033(2) Uani 1 1 d . . . H2 H 0.4851 0.1203 0.8985 0.04 Uiso 1 1 calc R . . C7 C 0.7039(13) 0.0810(4) 0.7345(10) 0.043(2) Uani 1 1 d . . . H7 H 0.7311 0.0765 0.8374 0.052 Uiso 1 1 calc R . . C8 C 0.7670(12) 0.0399(5) 0.6539(11) 0.044(2) Uani 1 1 d . . . H8 H 0.8412 0.0084 0.7005 0.053 Uiso 1 1 calc R . . C1 C 0.4373(10) 0.2084(4) 0.9494(10) 0.035(2) Uani 1 1 d . . . H1 H 0.399 0.1977 1.0295 0.041 Uiso 1 1 calc R . . C5 C 0.5412(9) 0.1772(4) 0.7486(8) 0.0277(18) Uani 1 1 d . . . H5 H 0.738(12) 0.022(4) 0.464(11) 0.03(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.03109(16) 0.02295(16) 0.02765(18) -0.00157(14) 0.00936(12) 0.00121(14) Br2 0.0460(5) 0.0376(6) 0.0292(5) -0.0005(4) 0.0101(4) -0.0037(4) Br1 0.0507(5) 0.0367(6) 0.0331(5) 0.0055(4) 0.0151(4) 0.0123(4) Br4 0.0534(6) 0.0393(6) 0.0588(6) 0.0002(5) 0.0326(5) -0.0034(5) Br3 0.0429(5) 0.0329(5) 0.0610(7) -0.0023(5) 0.0144(5) 0.0041(4) O1 0.042(3) 0.043(4) 0.036(4) -0.011(3) 0.010(3) 0.009(3) N2 0.057(5) 0.034(5) 0.048(6) -0.019(4) 0.026(5) -0.003(4) N1 0.023(3) 0.035(4) 0.029(4) -0.008(3) 0.004(3) -0.001(3) C3 0.040(5) 0.030(5) 0.036(5) 0.008(4) 0.013(4) -0.005(4) C10 0.049(6) 0.061(8) 0.032(5) -0.002(5) 0.007(5) 0.010(5) C6 0.029(4) 0.027(4) 0.026(4) 0.001(4) 0.009(3) -0.003(4) C9 0.031(4) 0.050(6) 0.030(5) 0.003(4) 0.009(4) 0.011(4) C4 0.027(4) 0.040(6) 0.027(5) 0.012(4) 0.012(3) 0.007(4) C2 0.036(5) 0.035(6) 0.026(5) 0.005(4) 0.006(4) 0.003(4) C7 0.075(7) 0.029(5) 0.028(5) -0.002(4) 0.018(5) 0.001(5) C8 0.052(6) 0.034(6) 0.045(6) 0.006(5) 0.013(5) 0.007(5) C1 0.038(5) 0.039(6) 0.031(5) -0.003(4) 0.017(4) -0.015(4) C5 0.024(4) 0.033(5) 0.025(4) 0.001(4) 0.005(3) 0.000(4) #----------------------------------------------------------------------------# # 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 O1 2.377(6) . ? Bi1 Br4 2.7012(10) . ? Bi1 Br1 2.7390(10) . ? Bi1 Br2 2.8530(9) . ? Bi1 Br3 3.0076(10) . ? Bi1 Br3 3.0979(10) 4_565 ? Br3 Bi1 3.0979(10) 4_665 ? O1 N1 1.367(8) . ? N2 C10 1.322(13) . ? N2 C8 1.371(13) . ? N2 H5 0.67(9) . ? N1 C1 1.344(11) . ? N1 C3 1.345(10) . ? C3 C4 1.385(12) . ? C3 H3 0.93 . ? C10 C9 1.380(12) . ? C10 H10 0.93 . ? C6 C9 1.374(11) . ? C6 C7 1.407(12) . ? C6 C5 1.448(11) . ? C9 H9 0.93 . ? C4 C5 1.394(12) . ? C4 H4 0.93 . ? C2 C1 1.367(12) . ? C2 C5 1.387(11) . ? C2 H2 0.93 . ? C7 C8 1.361(12) . ? C7 H7 0.93 . ? C8 H8 0.93 . ? C1 H1 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Bi1 Br4 85.46(15) . . ? O1 Bi1 Br1 84.11(15) . . ? Br4 Bi1 Br1 89.99(3) . . ? O1 Bi1 Br2 172.90(14) . . ? Br4 Bi1 Br2 97.50(3) . . ? Br1 Bi1 Br2 89.42(3) . . ? O1 Bi1 Br3 93.42(15) . . ? Br4 Bi1 Br3 88.05(3) . . ? Br1 Bi1 Br3 176.96(3) . . ? Br2 Bi1 Br3 93.14(3) . . ? O1 Bi1 Br3 83.82(15) . 4_565 ? Br4 Bi1 Br3 168.35(3) . 4_565 ? Br1 Bi1 Br3 93.43(3) . 4_565 ? Br2 Bi1 Br3 93.67(3) . 4_565 ? Br3 Bi1 Br3 88.045(15) . 4_565 ? Bi1 Br3 Bi1 150.38(4) . 4_665 ? N1 O1 Bi1 125.0(4) . . ? C10 N2 C8 124.1(9) . . ? C10 N2 H5 120(9) . . ? C8 N2 H5 115(9) . . ? C1 N1 C3 121.8(8) . . ? C1 N1 O1 119.4(7) . . ? C3 N1 O1 118.7(8) . . ? N1 C3 C4 120.0(8) . . ? N1 C3 H3 120 . . ? C4 C3 H3 120 . . ? N2 C10 C9 118.3(9) . . ? N2 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C9 C6 C7 118.4(8) . . ? C9 C6 C5 120.8(8) . . ? C7 C6 C5 120.7(7) . . ? C6 C9 C10 120.9(9) . . ? C6 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C3 C4 C5 119.5(8) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C1 C2 C5 120.9(9) . . ? C1 C2 H2 119.6 . . ? C5 C2 H2 119.6 . . ? C8 C7 C6 120.3(9) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 N2 117.9(9) . . ? C7 C8 H8 121.1 . . ? N2 C8 H8 121.1 . . ? N1 C1 C2 119.7(8) . . ? N1 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C2 C5 C4 118.1(8) . . ? C2 C5 C6 122.9(8) . . ? C4 C5 C6 119.0(7) . . ? _database_code_depnum_ccdc_archive 'CCDC 952310' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sad _audit_creation_date 2013-06-17T16:24:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H19 N4 O2, Bi Cl6, C2 H6 O S' _chemical_formula_sum 'C22 H25 Bi Cl6 N4 O3 S' _chemical_formula_weight 847.23 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 19.2567(8) _cell_length_b 13.3429(5) _cell_length_c 12.3084(7) _cell_angle_alpha 90 _cell_angle_beta 107.434(3) _cell_angle_gamma 90 _cell_volume 3017.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4022 _cell_measurement_theta_min 3.65 _cell_measurement_theta_max 30.02 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.135 _exptl_crystal_size_min 0.075 _exptl_crystal_density_diffrn 1.865 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.475 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.440 _exptl_absorpt_correction_T_max 0.615 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0837 _diffrn_reflns_av_unetI/netI 0.116 _diffrn_reflns_number 20645 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 30.02 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 4384 _reflns_number_gt 2374 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2i (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0199P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4384 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1143 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0607 _refine_ls_wR_factor_gt 0.05 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.582 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.14 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.108 10.257 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.148 0.159 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.125 0.123 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4301(2) 0.1362(3) 0.3608(3) 0.0363(10) Uani 1 1 d . . . H1 H 0.4467 0.1583 0.4359 0.044 Uiso 1 1 calc R . . C2 C 0.4081(2) 0.2038(3) 0.2752(3) 0.0347(10) Uani 1 1 d . . . H2 H 0.4105 0.272 0.2915 0.042 Uiso 1 1 calc R . . C3 C 0.3819(2) 0.1714(3) 0.1631(3) 0.0294(9) Uani 1 1 d . . . C4 C 0.3794(2) 0.0693(3) 0.1440(3) 0.0379(11) Uani 1 1 d . . . H4 H 0.3614 0.045 0.07 0.046 Uiso 1 1 calc R . . C5 C 0.4031(2) 0.0036(3) 0.2325(4) 0.0430(11) Uani 1 1 d . . . H5 H 0.4018 -0.065 0.2188 0.052 Uiso 1 1 calc R . . C6 C 0.35718(19) 0.2440(3) 0.0677(3) 0.0299(8) Uani 1 1 d . . . C7 C 0.3332(2) 0.3393(3) 0.0840(3) 0.0417(11) Uani 1 1 d . . . H7 H 0.3318 0.3586 0.156 0.05 Uiso 1 1 calc R . . C8 C 0.3114(2) 0.4054(3) -0.0052(4) 0.0497(12) Uani 1 1 d . . . H8 H 0.2969 0.4699 0.0068 0.06 Uiso 1 1 calc R . . C9 C 0.3321(3) 0.2870(4) -0.1288(4) 0.0548(14) Uani 1 1 d . . . H9 H 0.3306 0.2693 -0.2026 0.066 Uiso 1 1 calc R . . C10 C 0.3561(3) 0.2194(3) -0.0420(4) 0.0492(13) Uani 1 1 d . . . H10 H 0.3718 0.1564 -0.0569 0.059 Uiso 1 1 calc R . . C11 C 0.5316(6) 0.5582(8) 0.1675(12) 0.267(7) Uani 1 1 d . . . H11A H 0.544 0.6198 0.209 0.401 Uiso 0.5 1 calc PR . . H11B H 0.5112 0.5725 0.0878 0.401 Uiso 0.5 1 calc PR . . H11C H 0.5746 0.518 0.179 0.401 Uiso 0.5 1 calc PR . . H11D H 0.5552 0.6218 0.1879 0.401 Uiso 0.5 1 d PR . . H11E H 0.4825 0.5685 0.1201 0.401 Uiso 0.5 1 d PR . . H11F H 0.5577 0.5195 0.1266 0.401 Uiso 0.5 1 d PR . . Bi1 Bi 0.25 0.25 -0.5 0.02979(8) Uani 1 2 d S . . Cl1 Cl 0.23845(6) 0.41447(8) -0.37373(8) 0.0399(3) Uani 1 1 d . . . Cl2 Cl 0.22341(7) 0.12434(8) -0.34269(9) 0.0498(3) Uani 1 1 d . . . Cl3 Cl 0.39355(6) 0.23767(10) -0.38833(10) 0.0583(3) Uani 1 1 d . . . N1 N 0.42820(18) 0.0383(3) 0.3385(3) 0.0383(9) Uani 1 1 d . . . N2 N 0.31115(18) 0.3770(3) -0.1079(3) 0.0456(10) Uani 1 1 d . . . H2A H 0.2968 0.4189 -0.1632 0.055 Uiso 1 1 calc R . . O1 O 0.44896(16) -0.0302(2) 0.4228(2) 0.0559(9) Uani 1 1 d . . . O2 O 0.5 0.3914(6) 0.25 0.253(6) Uani 1 2 d S . . S1 S 0.4705(2) 0.4955(4) 0.2140(7) 0.190(3) Uani 0.5 1 d P . . H1A H 0.5 0 0.5 0.08(2) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.042(3) 0.034(3) 0.030(2) 0.0041(19) 0.005(2) -0.002(2) C2 0.043(3) 0.027(2) 0.032(2) 0.0021(19) 0.009(2) 0.001(2) C3 0.030(2) 0.027(3) 0.032(2) 0.0027(18) 0.011(2) 0.0009(18) C4 0.046(3) 0.033(3) 0.030(2) -0.0002(19) 0.006(2) 0.002(2) C5 0.045(3) 0.031(3) 0.049(3) -0.002(2) 0.008(2) 0.003(2) C6 0.0326(19) 0.031(2) 0.0270(18) -0.003(2) 0.0098(16) 0.001(2) C7 0.061(3) 0.036(3) 0.032(2) -0.001(2) 0.020(2) 0.016(2) C8 0.074(3) 0.036(3) 0.043(3) 0.004(2) 0.024(3) 0.019(2) C9 0.084(4) 0.051(3) 0.028(2) 0.000(2) 0.014(3) 0.013(3) C10 0.079(3) 0.034(3) 0.034(3) -0.0032(19) 0.015(3) 0.021(2) C11 0.300(14) 0.149(10) 0.48(2) 0.000(12) 0.313(15) -0.042(10) Bi1 0.04745(14) 0.02150(11) 0.02089(10) 0.00056(13) 0.01095(9) -0.00032(15) Cl1 0.0611(7) 0.0310(6) 0.0293(5) -0.0028(5) 0.0165(5) -0.0002(5) Cl2 0.0888(9) 0.0324(6) 0.0372(6) 0.0016(5) 0.0324(6) -0.0048(6) Cl3 0.0552(7) 0.0644(9) 0.0495(6) -0.0020(7) 0.0070(6) 0.0024(7) N1 0.036(2) 0.037(2) 0.038(2) 0.0121(18) 0.0055(18) -0.0057(17) N2 0.056(2) 0.050(3) 0.030(2) 0.0155(18) 0.0111(19) 0.017(2) O1 0.060(2) 0.045(2) 0.0499(19) 0.0279(16) -0.0037(18) -0.0028(17) O2 0.100(6) 0.054(6) 0.59(2) 0 0.074(9) 0 S1 0.074(3) 0.092(4) 0.386(11) 0.035(5) 0.041(5) -0.008(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.333(5) . ? C1 C2 1.355(5) . ? C1 H1 0.93 . ? C2 C3 1.389(5) . ? C2 H2 0.93 . ? C3 C4 1.381(5) . ? C3 C6 1.486(5) . ? C4 C5 1.366(5) . ? C4 H4 0.93 . ? C5 N1 1.331(5) . ? C5 H5 0.93 . ? C6 C10 1.383(5) . ? C6 C7 1.389(5) . ? C7 C8 1.372(5) . ? C7 H7 0.93 . ? C8 N2 1.318(5) . ? C8 H8 0.93 . ? C9 N2 1.318(5) . ? C9 C10 1.368(6) . ? C9 H9 0.93 . ? C10 H10 0.93 . ? C11 S1 1.679(11) . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C11 H11D 0.96 . ? C11 H11E 0.96 . ? C11 H11F 0.9601 . ? Bi1 Cl3 2.6983(11) 7_554 ? Bi1 Cl3 2.6983(11) . ? Bi1 Cl2 2.7233(10) . ? Bi1 Cl2 2.7233(10) 7_554 ? Bi1 Cl1 2.7364(10) 7_554 ? Bi1 Cl1 2.7364(10) . ? N1 O1 1.350(4) . ? N2 H2A 0.86 . ? O1 H1A 1.213(3) . ? O2 S1 1.516(7) 2_655 ? O2 S1 1.516(7) . ? S1 S1 1.215(10) 2_655 ? S1 C11 1.693(12) 2_655 ? S1 H11E 1.5805 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 120.6(4) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C1 C2 C3 120.1(4) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C4 C3 C2 117.4(4) . . ? C4 C3 C6 121.4(4) . . ? C2 C3 C6 121.1(4) . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C5 C4 119.7(4) . . ? N1 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C10 C6 C7 116.7(4) . . ? C10 C6 C3 121.7(4) . . ? C7 C6 C3 121.6(3) . . ? C8 C7 C6 120.5(4) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? N2 C8 C7 119.7(4) . . ? N2 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? N2 C9 C10 120.0(4) . . ? N2 C9 H9 120 . . ? C10 C9 H9 120 . . ? C9 C10 C6 120.6(4) . . ? C9 C10 H10 119.7 . . ? C6 C10 H10 119.7 . . ? S1 C11 H11A 109.5 . . ? S1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? S1 C11 H11D 132.5 . . ? H11A C11 H11D 23.1 . . ? H11B C11 H11D 96.2 . . ? H11C C11 H11D 97.8 . . ? S1 C11 H11E 67.4 . . ? H11A C11 H11E 104 . . ? H11B C11 H11E 47.5 . . ? H11C C11 H11E 144.9 . . ? H11D C11 H11E 109.5 . . ? S1 C11 H11F 116.1 . . ? H11A C11 H11F 130.8 . . ? H11B C11 H11F 72 . . ? H11C C11 H11F 38.3 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? Cl3 Bi1 Cl3 180.00(2) 7_554 . ? Cl3 Bi1 Cl2 91.01(4) 7_554 . ? Cl3 Bi1 Cl2 88.99(4) . . ? Cl3 Bi1 Cl2 88.99(4) 7_554 7_554 ? Cl3 Bi1 Cl2 91.01(4) . 7_554 ? Cl2 Bi1 Cl2 180.00(5) . 7_554 ? Cl3 Bi1 Cl1 90.27(4) 7_554 7_554 ? Cl3 Bi1 Cl1 89.73(4) . 7_554 ? Cl2 Bi1 Cl1 88.55(4) . 7_554 ? Cl2 Bi1 Cl1 91.45(4) 7_554 7_554 ? Cl3 Bi1 Cl1 89.73(4) 7_554 . ? Cl3 Bi1 Cl1 90.27(4) . . ? Cl2 Bi1 Cl1 91.45(4) . . ? Cl2 Bi1 Cl1 88.55(4) 7_554 . ? Cl1 Bi1 Cl1 180 7_554 . ? C5 N1 C1 121.4(4) . . ? C5 N1 O1 117.0(4) . . ? C1 N1 O1 121.5(3) . . ? C8 N2 C9 122.4(4) . . ? C8 N2 H2A 118.8 . . ? C9 N2 H2A 118.8 . . ? N1 O1 H1A 111.1(3) . . ? S1 O2 S1 47.2(4) 2_655 . ? S1 S1 O2 66.4(2) 2_655 . ? S1 S1 C11 69.5(6) 2_655 . ? O2 S1 C11 108.5(5) . . ? S1 S1 C11 68.2(8) 2_655 2_655 ? O2 S1 C11 107.7(6) . 2_655 ? C11 S1 C11 104.4(7) . 2_655 ? S1 S1 H11E 102.9 2_655 . ? O2 S1 H11E 130.9 . . ? C11 S1 H11E 34.1 . . ? C11 S1 H11E 111.8 2_655 . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 952311'